Vacation Rentals By Owner In Anna Maria, FL

Summary:brbrExperience the ultimate Anna Maria Island getaway at Tripletail! This stunning 4-bedroom, 4-bath bayfront home offers breathtaking waterfront views and is perfectly located near Pine Avenue and the City Pier. Enjoy mornings watching dolphins, afternoons by the private pool, and evenings relaxing in the hot tub. With beach access and a host of amenities, Tripletail promises an unforgettable vacation.brbrbrbrThe Space:brbrDesigned for both gathering and privacy, Tripletail’s layout is ideal for families and couples traveling together:brbrbrbrMain Level:brbrbrbrKing bedroom with waterfront accessbrbrbrbrSecond king bedroombrbrbrbrFully equipped kitchen, dining area, and family room with water viewsbrbrbrbrUpper Level:brbrbrbrTwo additional king bedrooms, each with private bathroomsbrbrbrbrCozy sitting area perfect for reading, games, or relaxing after beach daysbrbrbrbrGuest Access:brbrYou'll have exclusive access to the entire house, including all four bedrooms, four bathrooms, the living room, kitchen, dining room, laundry room, balconies, and front yard. Enjoy the convenience of a private entrance and amenities like the outdoor pool, hot tub, and BBQ grill. A personalized smart lock code ensures easy, keyless entry anytime after 4 PM.brbrbrbrThe Neighborhood:brbrExplore the best of Anna Maria Island's Beaches from our prime location! Our home is perfectly situated near Pine Avenue, a charming hub just around the corner, offering a delightful array of boutique shops, cozy cafes, and diverse dining options. You're also just moments away from the historic City Pier, perfect for a leisurely stroll or enjoying the sunset. For those seeking adventure, we provide adult bikes for exploring the island's scenic streets and paddleboards and a kayak for enjoying the calm bay waters.brbrbrbrGetting Around:brbrGetting around is easy! Tripletail is conveniently located near Pine Avenue, just a short walk from the beach, shops, and restaurants. The free island trolley has a stop on Pine Avenue, offering easy access to explore the island. You'll find free parking both on the property and on the street. For those arriving by air, the closest major airport is about an hour's drive away.brbrbrbrOther Things to Note:brbrHeated Pool, hot tub and fenced yard with turf.brbrbrbrFour adult bikes, paddle boards, kayak, beach chairs all included.brbrbrbrPlease review and agree to the Reservation Agreement. Rates and Availability are subject to change until reservation is completed. A deposit must be received in order to reserve the dates you desire.brbrbrbrPets- Non-Aggressive breeds, vaccinated & current on a flea prevention program allowed only with prior approval. Pet Fee and Pet Waiver Required. $300 per petbrbrAny unauthorized pets= 25% surchargebrbrbrbrTraveler must provide photo ID and guest listbrbrIf for some reason the property you booked is unavailable, we may offer to rebook the Traveler at another property, if a substantially similar property is available for the same period and under a new reservation. Owner is not responsible for events beyond our control, ie: inclement weather, storms, evacuations, etc. Travel Insurance is recommended and may be purchased independently from several sites (Red Sky Travel Insurance, Square Mouth, etc.)brbrbrbrDue to the extensive equipment provided at the home, there are additional documents required. The use of the bikes, SUP and Kayak require a signed Equipment Waiver for anyone 18+brbrbrbrAll Drivers of the property's Golf Cart must be 25, and provide a copy of a valid U.S. Driver's License and Insurance.brbrbrbrInteraction with Guests:brbrWe give our guests space to relax but are always available if needed! You’ll receive a personal smart lock code before check-in, and we’re just a message, call, or email away if you have any questions or need anything during your stay.brbrbrbrFor direct support, contact our office phone.

Tripletail | Beachfront | Pool | Hot Tub

Anna Maria, Florida, United States

Bed

Bath

Sleeps

$459.33

When you arrive at Anna Maria Island vacation rental home “A Mermaid's Tale” you are greeted with true island style and luxury. This 3 bedroom 3 bathroom home spaciously accommodates up to 6 guests with 1 King bed, 1 Queen bed, 2 Twin beds and endless charm. Located in the coveted North End near Bean Point of the island in the city of Anna Maria “A Mermaid's Tale” is around the corner and across the street from powder soft Gulf of Mexico beaches. brbrInside this Anna Maria vacation rental home find an abundance of style and all the amenities you look for from the perfect vacation destination. A designer decorated home, each of the bedrooms are equipped with premium linens, luxury decor and plenty of space. The master suite is absolutely stunning with balcony access and a King bed. The master bathroom is gorgeous and truly luxurious with a large tiled walk in shower, double sinks and an oversized garden tub making for the most relaxing soak you’ll ever have. Relax on the designer furnishings in either the second floor living room or first floor den and take advantage of the wireless internet. When moving luggage and groceries take the elevator! brbrThe kitchen has new granite counter tops along with stainless appliances, a dishwasher, and room for three at the center island counter. The kitchen, living and dining room, all located on the second floor, have the perfect layout for entertaining and open up to the second floor screened porch area overlooking the pool. Fire up the propane grill, and dine al fresco on the sun deck or covered ground level pool side dining area. Also take in a sunset from your private rooftop terrace!brbrWhen you are ready to explore the island walk down North Shore to Pine Avenue where you will find both north and southbound free trolley stops. The free trolley runs almost the entire length of the island and passes by tons of dining and shopping options. Leave your car in one of the three parking spaces, and never worry about where to park! brbrFor a relaxing and stylish Anna Maria Island vacation reserve “A Mermaid's Tale” today!brbrDon’t see availability for your exact dates, give our office a call 941-778-6066.brbrTo be eligible for a refund, less our $250 cancellation fee, guests must cancel in writing outside 60 days from arrival.brbrVRC18-000078brbrMax Vehicles Allowed: 2 Max Day Guests Allowed: 2brbrPlease be sure to obey all traffic laws and be sure you are parking in a permitted area if parking on the streets. If you park in a non-parking zone or against traffic, you will be ticketed.brbrIMPORTANT INFORMATION:brbrYour booking is with Island Real Estate Vacations. We will send you check-in instructions 30 days prior to your arrival date. Please review the cancellation policy prior to booking. Island Real Estate Vacations will charge your credit card for your deposit payment. You will also see a separate charge by VRBO for their service fee.brbrPayment of reservation deposit is considered acceptance of all terms regardless of signature status of contract. Guest is responsible for adhering to the rental terms and dates. Any error on Guest’s part is not the responsibility of the agent. Sub-leasing of your vacation rental is strictly prohibited. A mid-stay clean and charge equal to the standard cleaning fee are required for all stays 21 nights or longer. By providing your phone number, you agree to receive text messages from our company. Message and data rates may apply. Message frequency varies.brbrYour final balance is due 60 days prior to your arrival date. Please note unless alternative arrangements are made, the bank account or credit card on file will be charged your remaining balance automatically at 60 days. If you do not wish to pay with the bank account or credit card on file, please reach out to pay several days in advance of 60 days prior to your arrival. If you initially paid with an eCheck and received the booking incentive, please remember future payments must also be made with an eCheck. Thank you for choosing eCheck to help reduce the cost of business. Please note the eCheck payment option cannot be used within 14 days of arrival. Any refunds on checks and echecks will be delayed at least 14 days after deposit or until funds are verified.brbrAll our properties provide luxury linens for you to enjoy during your stay.brbrAnna Maria Island’s noise ordinance aims to ensure citizens can enjoy a peaceful environment. The ordinance applies to all areas of the city, including public and private property, and places of business. It defines noise as any sound that annoys or disturbs a reasonable person of ordinary sensibilities or causes or tends to cause an adverse physical or psychological effect on such reasonable person. The noise ordinance limits the maximum permissible noise levels to: brbr7 AM–10 PM: 65 decibels: (Consistently shouting in the pool exceeds 65 decibels)br10 PM–7 AM: 50 decibels: (An audible conversation from 50’ or 15 meters away exceeds 50 decibels)brbrThe ordinance also prohibits plainly audible noise, which refers to any sound that can be clearly heard by a person using their normal hearing faculties. This means that a person can still be in violation if the noise can be easily heard by responding officers from a distance of 100 feet from the property line. Fines for excessive noise can range from $100 to $1,000.

A Mermaid's Tale - By Island Real Estate Vacations

Anna Maria, Florida, United States

Bed

Bath

Sleeps

$475.32

BRAND NEW POOL!brbrLocated on the coveted northern end of Anna Maria Island, “Maria's Way” is a charming beach cottage offering three bedrooms and two bathrooms. Sleeping up to six guests with two king beds and two twins; this single-family Anna Maria vacation rental home has just been updated with a designer flare. Walk to Bean Point, the best beach on west coast of Florida, and enjoy the secluded sugar sand beach. brbr“Maria's Way” spaciously accommodates guests with all the amenities of a fabulous beach vacation. Inside this Anna Maria Island vacation rental find a comfortable old Florida cottage feel with a stylish modern update. The kitchen has all the basics including a dishwasher and beautiful counters with seating for six. The dining room seats everyone comfortably or have a snack on the screen front porch. Kick back in the living room and enjoy five smart TVs throughout the home, perfect for streaming your favorite shows, along with wireless internet. There is a full bathroom in the master bedroom and a full bathroom just off the living room. “Maria's Way” has great outdoor space. brbrNestled in the heart of Anna Maria, from “Maria's Way” walk to the City Pier. You can use the three complimentary bikes to get around the island with ease, and take advantage of the beach wagon, four chairs, beach umbrella, cooler, and four ice packs for a comfortable and convenient day at the beach. When the day is done, go for a relaxing swim in the pool.brbrThere are plenty of fun things to do when staying on the Anna Maria Island. Nearby is the Pine Avenue shopping district with unique shops, dining and great ice cream from Two Scoops. Catch the free trolley on Pine Avenue and head south passing nearly everything this narrow barrier island has to offer. Going off Island Anna Maria is located on the West coast of Florida 45 minutes south of Tampa and 30 minutes north of Sarasota. Come down for Baseball spring training in nearby Bradenton and Sarasota. brbrReserve “Maria's Way” and make this your holiday destination!brbrDon’t see availability for your exact dates, give our office a call 941-778-6066.brTo be eligible for a refund, less our $250 cancellation fee, guests must cancel in writing outside 60 days from arrival.brbrIMPORTANT INFORMATION:brbrYour booking is with Island Real Estate Vacations. We will send you check-in instructions 30 days prior to your arrival date. Please review the cancellation policy prior to booking. Island Real Estate Vacations will charge your credit card for your deposit payment. You will also see a separate charge by VRBO for their service fee.brbrPayment of reservation deposit is considered acceptance of all terms regardless of signature status of contract. Guest is responsible for adhering to the rental terms and dates. Any error on Guest’s part is not the responsibility of the agent. Sub-leasing of your vacation rental is strictly prohibited. A mid-stay clean and charge equal to the standard cleaning fee are required for all stays 21 nights or longer. By providing your phone number, you agree to receive text messages from our company. Message and data rates may apply. Message frequency varies.brbrYour final balance is due 60 days prior to your arrival date. Please note unless alternative arrangements are made, the bank account or credit card on file will be charged your remaining balance automatically at 60 days. If you do not wish to pay with the bank account or credit card on file, please reach out to pay several days in advance of 60 days prior to your arrival. If you initially paid with an eCheck and received the booking incentive, please remember future payments must also be made with an eCheck. Thank you for choosing eCheck to help reduce the cost of business. Please note the eCheck payment option cannot be used within 14 days of arrival. Any refunds on checks and echecks will be delayed at least 14 days after deposit or until funds are verified.brbrAll our properties provide luxury linens for you to enjoy during your stay.brbrbrVR21-000010brbrPets: Yes, 2 Up to 75LBS Max Vehicles Allowed: 2 Max Day Guests Allowed: 2br• Dog Friendly - fee of $250 plus tax per dog.brbrPlease be sure to obey all traffic laws and be sure you are parking in a permitted area if parking on the streets. If you park in a non-parking zone or against traffic, you will be ticketed.brbrAnna Maria Island’s noise ordinance aims to ensure citizens can enjoy a peaceful environment. The ordinance applies to all areas of the city, including public and private property, and places of business. It defines noise as any sound that annoys or disturbs a reasonable person of ordinary sensibilities or causes or tends to cause an adverse physical or psychological effect on such reasonable person. The noise ordinance limits the maximum permissible noise levels to: br7 AM–10 PM: 65 decibels: (Consistently shouting in the pool exceeds 65 decibels)br10 PM–7 AM: 50 decibels: (An audible conversation from 50’ or 15 meters away exceeds 50 decibels)brThe ordinance also prohibits plainly audible noise, which refers to any sound that can be clearly heard by a person using their normal hearing faculties. This means that a person can still be in violation if the noise can be easily heard by responding officers from a distance of 100 feet from the property line. Fines for excessive noise can range from $100 to $1,000.

Marias Way - 3BR/2BA Pool Home - Anna Maria City -By Island Real Estate Vacation

Anna Maria, Florida, United States

Bed

Bath

Sleeps

$730.21

Welcome to the serene luxury of Bayside Bliss which is a fully remodeled three-bedroom/three-bathroom, ground level cottage north of Pine Avenue in the City of Anna Maria. You are only 2 houses away from the Bay beach! Enjoy easy Island life surrounded by tropical landscaping. It sleeps up to 8 guests. The open floor plan streamlines the living area, kitchen, and dining room. There is plenty of seating in the large living room with its large flat screen TV for your viewing pleasure and ...sleeper sofa. The beautiful, high-end kitchen is suited for all levels of chefs. It is stocked with everything you will need for light lunch or to prepare your catch of the day! There is an eat-in kitchen island and a dining room table for the whole family. A second King Ensuite bedroom is on the other side of the house for a convenient split layout. brbrHIGHLIGHTSbrbrPrivate pool/spabrbrPool COOLING for hot summer days!brbr278 sq ft. of screened in patiobrbrPet friendly propertybrbr0.1 miles from bay access brbr0.7 miles from beach accessbrbrBEDROOMSbrbrSleeps 8brbrPrimary Bedroom: Ensuite King brbrSecond Bedroom: Ensuite KingbrbrThird Bedroom: Two TwinsbrbrBATHROOMSbrbrPrimary Ensuite: Walk-in ShowerbrbrSecond Bathroom: Shower/Tub CombobrbrThird Ensuite: Walk-in Shower brbrEXTERIORbrbrBring your family and enjoy all the amenities Bayside Bliss has to offer for time well spent together! Tucked away in a quiet side street on the sought-after North end of the island you can relax out-back on the screened in lanai. Enjoy the brand new, large 26' x 12' salt water pool with heating/cooling year round and spa in the backyard! There is a $150 pool fee per week in addition. brbrStroll to the beach and soak up the sun! Return, freshen up and explore Pine Avenue for shopping or eating out, take in the Bay water views and the lights of the Sunshine Skyway at night on the Rod and Reel Pier. brbrThe weekly pool heat/cool fee is $150.00. Pool heaters in private homes are locked for your safety and controls must not be tampered with as they are monitored by the pool company. 86 F is the highest heat temperature setting which might not be always reached. Please note if cold days and nights occur, water temperatures will drop and may stay cooler longer. Pool heaters will not operate and will automatically shut down if outside temperatures get too cold. While we take every precaution to ensure that pools are heated as specified, weather conditions may affect the temperature of the pool. Nothing can be done about this issue. Outdoor spas are not hot tubs and require heat at the additional cost. The temperature of a spa is typically set at the same temperature as the pool. In the event of pool equipment malfunction during your stay, Duncan Real Estate will expedite repairs as quickly as possible. It may be necessary to close swimming pools for maintenance purposes. No refund or rent adjustment will be made for circumstances beyond our control, malfunctions, or loss of use of equipment or amenities. brbrBayside Bliss has three parking spots reserved for guests. brbrBayside Bliss is a pet friendly property for dogs up to 50 lbs. The non-refundable pet fee is $150.00 per pet and will be charged for each week. Short stays are not prorated. The pet fee does not cover any damage caused by the pet.brbrPlease no smoking anywhere on this property. Thank you.brbrPlease keep in mind that you are vacationing in a residential area. Please be a good neighbor by keeping the noise to a respectful level during the day and night. Excessive and unreasonable noise can deprive neighbors of the peaceful enjoyment of their private property.brbrAmenities Include:brbr- Bedroom 1 King Ensuitebrbr- Bedroom 2 King Ensuitebrbr- Bedroom 3 2 Twinsbrbr- Extra Beds Queen Sleeperbrbr- Queen Sleeperbrbr- Work Spacebrbr- Bathroom 1 Walk-in Showerbrbr- Bathroom 2 Shower/Tubbrbr- Bathroom 3 Walk-in Showerbrbr- Beach Access 0.7 milesbrbr- Bay Access 0.1 milesbrbr- Ground Levelbrbr- Central A Cbrbr- Sqft under a c 1650brbr- Free Parkingbrbr- Parking Spotsbrbr- Dogs up to 50 lbsbrbr- Bath Towelsbrbr- Beach Towelsbrbr- Hair Dryerbrbr- Ice Makerbrbr- Drip Coffee maker Dripbrbr- Dishwasherbrbr- High Speed WIFIbrbr- TV 5brbr- TV Streaming Onlybrbr- Washerbrbr- Ironbrbr- Smoke Alarmbrbr- Private Poolbrbr- Pool Dimensions 26'x12'brbr- Spabrbr- Screened Lanaibrbr- Propane Grillbrbr- Fire Pitbrbr- Beach Amenitiesbrbr- Exterior Outlet L side of housebrbr

Bayside Bliss by Duncan Real Estate

Anna Maria, Florida, United States

Bed

Bath

Sleeps

$1059.62

Coconut Hut by Anna Maria Life Vacation Rentalsbr213 Coconut Ave, Anna Maria, FL 34217brbrWhat You'll Love About This Home:brLocation! Less than 1 Block to Beach! North of Pine Ave!br3 Bed / 3.5 Bathbr1 King & Twin & Twin Trundle in connecting office, 1 King, 1 Twin & Twin/Twin BunkbedbrPrivate Heated Pool & SpabrPool LoungersbrPoolside Cabana Hut with Bathroom & TVbrPatio Dining for 6brGas GrillbrPool TablebrPutting GreenbrKeurigbrProfessional Linen Service, Washer & DryerbrComplimentary WIFIbrBeach Towels, Beach Chairs, Beach WagonbrParking for 2 CarsbrbrDetails:brLocated on the block to the beach and 2.5 blocks to Pine Ave, Coconut Hut is your North End vacation home!brbrThe bright and welcoming living space features the kitchen, living and dining rooms. A dining table for six and kitchen counter bar seating provide room for all to enjoy a meal. brbrThe master bedroom features a king-sized bed, an office den with a twin bed and twin trundle, and an ensuite bathroom. This bedroom also includes patio doors which lead to an outdoor seating area. One of the guest rooms has a king bed and ensuite bathroom and the final guest room includes a twin bed and twin over twin bunkbeds. Each bedroom includes a TV, and crisp linens and plush towels from our professional linen company.brbrYour guests will stay connected with complimentary WIFI and enjoy all of the comforts of home, including a washer and dryer.brbrA sparkling, heated pool and spa highlight the backyard and is complete with pool loungers and Adirondack chairs for relaxing. Guests will enjoy grilling and dining poolside at the patio table for six. A pool table and putting green add to the fun.brbrCoconut Hut is easy walking distance to many shops and restaurants, and to the free island trolley, which travels the entire length of the 7 miles of the island. Hop on and off at your leisure and explore shopping, dining and the beaches. The perfect location for your next beach vacation!brbrYou are vacationing in a residential area. Please be a good neighbor by keeping the noise to a respectful level during the day and night. Excessive and unreasonable noise can deprive neighbors of the peaceful enjoyment of their private property.brbrBedroom 1: King bed, attached office den with a Twin bed and Twin trundle, Ensuite Bathroom, TV on Floor 1brBedroom 2: King bed, Ensuite Bathroom, TV on Floor 1brBedroom 3: Twin bed, Twin over Twin bunkbeds, TV on Floor 1brbrPlease note:brPets are not allowed in this home.brAmenities are subject to change.brbrVR16-000395 brbrGolf Cart DEAL ALERT!!! brReserve now a street legal GOLF CART from Fun & More Rentals! 4, 6 or 8 passenger gas or electric carts to choose.brFUN way to explore the island for the entire family.brMention Anna Maria Life Vacation Rentals and receive this VIP deal!brwww.FunAndMoreRentals.combr941-462-2719brbrIMPORTANT INFORMATION: brbrYour booking is with Anna Maria Life Vacation Rentals. We will send you check-in instructions 14 days prior to your arrival date. We will send you our rental agreement in an electronic signature document. Please review and return to us by following the instructions.brbr** Your signed rental agreement must be returned in order to receive your check-in details. brbrVRBO BOOKINGSbrbrAnna Maria Life Vacation Rentals will charge your credit card for your deposit payment. You will also see a separate charge by VRBO for their service fee. brbrYour final balance is due 60 days prior to your arrival date. We will send you a final payment reminder 90 days prior to arrival. We do not automatically charge your card for your final balance. brbrThe instructions for making your final payment will be included in your final payment reminder.brbrPlease review the cancellation policy prior to booking. brbrGOOGLE VACATION RENTAL BOOKINGSbrbrYour payment is due in full at the time of booking and the final balance information above does not apply to your reservation.

Coconut Hut: Pool & Spa, Pool Table, Putting Green by Anna Maria Life Vacation Rentals

Anna Maria, Florida, United States

Bed

Bath

Sleeps

$1274.64

***Photos Updated September 2025***brExperience the ultimate waterfront getaway at this stunning bayfront property in Anna Maria. With breathtaking views of the bay, inviting outdoor spaces, and plenty of amenities, this home is the perfect retreat for family and friends. Two kayaks and a paddle board are included for guests to enjoy exploring the calm bay waters right from the backyard.brbrThe main floor features an open-concept living area with sweeping water views that extend out over a large sun deck. This level includes a master bedroom with a King bed and TV, as well as a second bedroom with a California King and TV. Both rooms share a convenient hallway bathroom.brbrThe lower level offers a third bedroom with two twin beds, a TV, and direct pool patio access, along with a full bathroom with a walk-in shower.brbrStep outside to your private tropical oasis. The heated pool and expansive deck provide plenty of space to relax, dine, and gather. Whether it’s morning coffee on the sun deck, afternoons by the pool, or sunrise views over the bay, the outdoor areas are designed for making the most of the Anna Maria Island lifestyle.brbrBedroom Details:brBedroom 1: King Bed w/ TVbrBedroom 2: California King Bed w/ TVbrBedroom 3: Two Twin Beds w/ TV & Direct Pool Patio Accessbrbr***OVERCROWDING CONSEQUENCES***brMaximum occupancy of rental homes on Anna Maria Island are set by the Cities and are strictly enforced. An occupant is any person staying overnight, regardless of the number of nights. Due to recent issues of overcrowding in the area, if maximum occupancy is exceeded during your stay, a $1000 (one thousand dollar) overcrowding fee will be charged to the payment method on file and your party will be immediately evicted. We appreciate your understanding and cooperation to keep Anna Maria Island enjoyable for everyone.

Sea La Vie AM: Bay front, pool, hot tub, rooftop deck, and water sports gear!

Anna Maria, Florida, United States

Bed

Bath

Sleeps

$1053.76

Summary:brbrEscape to Waves, a stunning house on Anna Maria Island, offering luxurious comfort and direct beach access. Perfectly positioned just across the street from the beach, Waves offers stunning water views and the convenience of stepping from your front door to the sugar-white sands in moments.brbrbrbrThe Space:brbrThe home has been redesigned from top to bottom, blending contemporary coastal style with relaxed comfort, making it ideal for families, couples, and friends traveling together. The open-concept living space is bright and inviting, perfect for gathering. It features plush seating, large windows, and soft Gulf breezes, creating a calming atmosphere for movie nights, conversations, and relaxation. The gourmet kitchen is equally impressive, featuring stainless steel appliances, granite countertops, and generous prep space for group meals. The dining area provides seating for shared moments and memories. Each bedroom is thoughtfully designed to deliver comfort and privacy: The Primary Suite offers a king bed, a spa-like en-suite bath with a walk-in shower, and a private balcony with water views. There are three additional bedrooms, providing cozy and stylish accommodations ideal for families and groups. Three full bathrooms offer convenience for everyone.brbrbrbrGuest Access:brbrGuests have exclusive access to a private heated pool, perfect for year-round enjoyment, and a putting green for some friendly competition. Enjoy water views from multiple outdoor spaces and take advantage of quick and easy beach access just steps away. Included are adult bikes, a paddle board (SUP), and a kayak for your enjoyment. A complimentary 6-passenger golf cart is also provided.brbrbrbrThe Neighborhood:brbrExperience the beauty of Anna Maria Island's north end. From its powdery white sand beaches to its charming, eclectic boutiques and restaurants, the north end of Anna Maria Island is a must-see destination. Take in the stunning views of the Gulf of Mexico and explore all that the sea has to offer. Relax and soak up the sun on the beach, or challenge yourself with a variety of outdoor sports and activities sure to create lasting memories. Soak up the atmosphere and enjoy the local vibe of this picturesque island paradise. With so much to do and see, you won't want to miss out on the incredible beauty of the north end of Anna Maria Island.brbrbrbrGetting Around:brbrIdeally situated on Anna Maria Island's walkable North End, offering easy access to the beach, Bean Point, and the shops and restaurants of Pine Avenue. For exploring further, the free island trolley provides convenient transportation, with a stop located right on Pine Ave. Free parking is available on the premises and on the street. The closest major airport is approximately a 1-hour drive away.brbrbrbrOther Things to Note:brbrPlease review and agree to the Reservation Agreement. brbrRates and Availability are subject to change until reservation is completed. A deposit must be received in order to reserve the dates you desire. brbrbrbrPets- Non-Aggressive breeds, vaccinated & current on a flea prevention program allowed only with prior approval. Pet Fee and Pet Waiver Required. brbr$300 per pet Any unauthorized pets= 25% surcharge brbrbrbrTraveler must provide photo ID and guest list brbrIf for some reason the property you booked is unavailable, we may offer to rebook the Traveler at another property, if a substantially similar property is available for the same period and under a new reservation. Owner is not responsible for events beyond our control, ie: inclement weather, storms, evacuations, etc. Travel Insurance is recommended and may be purchased independently from several sites (Red Sky Travel Insurance, Square Mouth, etc.) brbrbrbrDue to the extensive equipment provided at the home, there are additional documents required. brbrThe use of the bikes, SUP and Kayak require a signed Equipment Waiver for anyone 18+ brbrbrbrAll Drivers of the property's Golf Cart must be 25, and provide a copy of a valid U.S. Driver's License and Insurance.brbrbrbrInteraction with Guests:brbrWe give our guests space to relax but are always available if needed! You’ll receive a personal smart lock code before check-in, and we’re just a message, call, or email away if you have any questions or need anything during your stay. brbrbrbrFor direct support, contact our office phone.

Waves | Heated Pool | Steps to Beach | Golf Cart

Anna Maria, Florida, United States

Bed

Bath

Sleeps

$597.8

521 Spring Ave, Anna Maria, FL 34216brWhat You'll Love About This Home:brbrLocation! 2 Houses from the Bay! 5 Blocks to Gulf!br2 Bedrooms / 2 Bathroomsbr2 KingsbrPrivate Heated PoolbrPool Loungers & UmbrellasbrCovered Canopy Outdoor Furnished Lounge AreabrUmbrella Patio Dining for 4 - Pool LevelbrUmbrella Patio Dining for 4 - Verandah off Main Living AreabrGas GrillbrGame Room with Pool & Ping Pong, TV & Lounge FurniturebrCorn HolebrKeurig & Drip Coffee MakerbrProfessional Linen Service, Washer & DryerbrComplimentary WIFIbrBeach Towels, Chairs, WagonbrDriveway Parking for 2 CarsbrbrDetails:brWelcome to your Decked Out, perfectly situated just two houses from the bay and only five blocks from the gorgeous Gulf of Mexico beaches. brbrThis bright, coastal-inspired living room is the perfect place to unwind during your vacation. The space features rich hardwood floors, a spacious leather sectional with plush pillows, and two woven accent chairs that create a warm, inviting atmosphere. Large windows and French doors fill the room with natural light and offer lush tropical views, enhancing the relaxing getaway feel. The kitchen is stocked with both a Keurig and drip coffee maker, giving you options for the perfect morning brew. You'll also enjoy the convenience of a washer and dryer, professional linen service, and complimentary WIFI throughout the home. brbrThis beautifully appointed 2-bedroom, 2-bathroom home offers the perfect blend of comfort, style, and coastal luxury, The master bedroom features a plush king-sized bed, its own ensuite bathroom, and private balcony access, creating a peaceful retreat for morning coffee or evening relaxation. The guest room offers a comfortable queen bed and access to a private balcony, allowing guests to step outside and enjoy fresh island breezes at any time of day. Both bedrooms include a TV and are thoughtfully designed with serene décor and high-quality linens, from our professional linen service, ensuring every guest sleeps well and wakes refreshed for another day in paradise. br brStep outside and discover your own private paradise. The heated pool invites you to take a refreshing dip year-round, while pool loungers and umbrellas ensure you can soak up the Florida sun in total comfort. Enjoy meals al fresco at the umbrella-shaded poolside dining area for four, or head up to the verandah off the main living area, where an additional covered dining space—also for four—offers lovely views and cool breezes. Fire up the gas grill for an evening barbecue, then unwind beneath the furnished canopy lounge area, surrounded by swaying palms and the peaceful sounds of island life.brbrFor indoor fun, the home features a fully equipped game room, complete with pool table, ping pong, TV, and comfortable lounge seating—perfect for family game nights or a break from the sun. Outdoors, enjoy a round of corn hole in between dips in the pool.brbrEverything you need for the beach is ready and waiting—beach towels, chairs, and a wagon for easy transport. Parking is a breeze with a driveway that accommodates two cars.brbrWhether you're relaxing by the pool, strolling to the bay at sunset, or spending the day on the Gulf's powder-soft sand, this home offers all the amenities and atmosphere you need for a truly unforgettable vacation.brbrBedroom 1 - King Bed, Ensuite Bathroom, Balcony, TVbrBedroom 2 - Queen Bed, Balcony, TVbrbrPlease note:brThis home is not pet friendly.brAmenities are subject to change.brDriveway parking is available for a maximum of 2 cars. Parking for additional cars is not available. brbrYou are vacationing in a residential area. Please be a good neighbor by keeping the noise to a respectful level during the day and night. Excessive and unreasonable noise can deprive neighbors of the peaceful enjoyment of their private property. The maximum occupancy is four.brbrVR16-000136

Decked Out: Steps to Bay & Beach, Pool, Games by Anna Maria Life Vacation Rentals

Anna Maria, Florida, United States

Bed

Bath

Sleeps

$462.2

Welcome to Anna Maria Aloha!brOn Anna Maria Island (Anna Maria, Florida)brbrExperience Anna Maria Aloha — a tranquil island cottage made for rest, renewal, and connection.brbrNestled on the peaceful North End of Anna Maria Island, just 500 feet from the soft white sands of the Gulf—no streets to cross—this single-level home invites you to breathe deeply, slow down, and savor the island's easy rhythm.brbrPerfect for: couples, small families, and travelers seeking a calm coastal retreat.brbrHighlightsbr- Ground-level home on beach block—about 500 ft to the Gulf of Mexicobr- 3 Bedrooms | 2 Full Baths (1 King Suite, 1 Queen Bedroom, 1 Custom Bunk Room)br- Outdoor dining area with grill and showerbr- Fully equipped kitchen with stainless-steel appliancesbr- Open living and dining spaces with Smart TV and cablebr- Pet-friendly with prior approval (see policies)br- Beach gear rental credit includedbrbrInterior SpacesbrStep inside to an open layout filled with soft coastal hues, warm textures, and sunlight drifting through the windows. The living room centers around a comfortable sofa and Smart TV — a space for quiet mornings, unhurried evenings, and easy connection.brbrThe layout flows naturally between living, dining, and kitchen spaces, creating a sense of calm and togetherness.brbrKitchen & DiningbrThe kitchen is simple, inviting, and fully equipped for relaxed island meals. Stainless-steel appliances and open shelving keep the space bright and functional.brbrYou'll find everything you need for breakfast before the beach or dinner after sunset:br- Stove / oven, microwave, dishwasher, refrigerator with freezer and ice makerbr- 12-cup coffeemaker, blender, and toasterbr- Cookware, dishes, and utensils for sixbrbrGather around the dining table for family meals or step outside to enjoy dinner in the soft evening air.brbrBedrooms & Bathsbr- Each bedroom is designed for rest and comfort, blending coastal charm with thoughtful simplicity.br- Primary King Suite: Private bath with tub/shower combo, Smart TV, and easy access to the outdoor shower for rinsing off sandy toes.br- Queen Bedroom (Maui Room): Bright, airy, and comfortable, with Smart TV and soft natural light.br- Bunk Room (Kauai Room): Custom twin XL bunks and Smart TV — a cheerful space for kids or extra guests.br- Second Full Bath: Convenient hall access with tub/shower combo and fresh white towels.brbrLayout Overviewbr- Single-level home (no stairs inside)br- Open-concept living, dining, and kitchen areabr- Three bedrooms and two full bathsbr- Laundry closet with washer and dryerbr- Covered outdoor patio with grill and dining spacebrbrOutdoor LivingbrStep outside to your private backyard haven — a space designed for slowing down and breathing in the salt air. Enjoy your morning coffee beneath the palms, rinse off in the outdoor shower after the beach, or share dinner as the sky turns gold.brbrShaded seating offers a comfortable place to relax, while the soft hum of the island sets the pace for the evening ahead.brbrOutdoor Highlightsbr- Dining table and lounge chairsbr- Gas grill (propane provided)br- Outdoor showerbr- Short walk to beach access (approx. 500 ft)br- Trolley stop nearby for island exploringbrbrAdditional Amenitiesbr- Wireless internet and cable televisionbr- Central A/C and heatbr- Washer and dryerbr- Professionally laundered linens and towelsbr- Hair dryer, iron, and ironing boardbr- Beach towels providedbr- Beach gear rental credit included (chairs, umbrellas, carts — details provided after booking)brbrParkingbr- Driveway accommodates 1–2 vehiclesbrbrAnna Maria Aloha welcomes guests who value care, connection, and simplicity. From its walkable location near Pine Avenue's local cafés and shops to the quiet rhythm of its beachside neighborhood, this home offers the comfort of slowing down — and the space to enjoy it.brbrWrite your vacation story here, where life moves with the tide and every sunrise feels like an invitation.brbrPoliciesbrbrPlease Remember: You are vacationing in a residential area. Please be a good neighbor by keeping the noise to a respectful level during the day and night. Excessive and unreasonable noise can deprive neighbors of the peaceful enjoyment of their private property. *Exceeding the noise ordinance could result in disciplinary actions including fines and/or termination of your rental agreement without refund.brbrNO SMOKING.brbrPets are welcome with prior approval, provided they meet our pet policy guidelines. We allow a maximum of two pets, each weighing under 65 lbs. A pet fee applies based on the length of your stay: $100 for stays under 4 days, $200 for stays of 4-14 days, and $400 for stays of 15+ days, per pet.brbrBooking & Fee PolicybrInclude all guests and pets in your reservation request for accurate pricing. Additional fees apply for extra occupancy (over 2 guests per bedroom) or undeclared pets.brbrOptional Services (subject to approval)brEarly check-in/late departure, elevator access, and mid-stay cleaning for stays of 28+ days. Fees for approved add-ons are collected after booking.brbrReservations & Guest RequirementsbrMost stays are 7 nights, Saturday–Saturday, though flexible dates may be available outside peak/holiday weeks—confirm before booking, as changes are not always possible afterward. Guests must be 25+, provide valid ID, and remain for the full stay. Standard occupancy is 2 per bedroom; extra guests are $25/person/night up to the maximum allowed.brbrQuiet Hoursbr10 PM–8 AM. Maintain reasonable noise at all times to respect neighbors; excessive noise is not permitted.brbrCleaning & LinensbrHome is professionally cleaned and sanitized between stays. Starter amenities provided; daily service available for a fee. Stays of 28+ days require a mid-stay clean. Linens/towels are commercially laundered through our Professional Linen Program; no extra sets stored onsite.brbrGolf Cart RentalsbrExplore the island with ease! After booking, reserve a golf cart through our sister company, Once Upon A Beach Carts, and enjoy an exclusive discount available only to our vacation rental guests.brbrProperty SecuritybrExterior cameras may monitor entries, driveways, pool equipment, and backyard access for security, deliveries, and occupancy compliance. Cameras do not face private areas.brbrPayments & Cancellation PolicybrPolicies updated October 6, 2025 — see full Terms & Conditions for details.brbrPayment SchedulebrDepositbr- Reservations up to 20 days: 50% of total amount due at time of booking.brRemaining Balancebr- Reservations up to 20 days: Remaining 50% due 30 days prior to check-in.brbrCancellation PolicybrFor Reservations of 20 Days or Lessbr- More than 30 days before arrival: Full refund of deposit (including taxes) minus non-refundable booking administration fee.br- 14–29 days before arrival: Refund of 50% of total rental, fees, and taxes, minus non-refundable booking administration fee.br- Less than 14 days before arrival: Refunds only for base rental rate, fees, and taxes for nights we are able to rebook, minus non-refundable booking administration fee.br- Please note: While we make every effort to rebook, we cannot guarantee the same rate or number of nights. For any nights that cannot be re-rented, as well as for non-arrivals, late arrivals, early departures, or alterations resulting in lost revenue, no refunds or price adjustments will be made.brbrTravel InsurancebrCSA Travel Insurance is available to U.S. guests (except NY and HI residents) and is strongly encouraged to protect your trip from unforeseen events. No refunds are given for COVID-19, weather, or beach conditions outside our cancellation policy. Hurricane season runs June 1–Nov 30; insurance can safeguard your plans. In the event of a mandatory evacuation, home unavailability, or government order halting vacation rentals, guests receive a full refund of base rate, applicable fees (minus booking fee), and taxes.brbrAdditional TermsbrNo refunds for events beyond our control (weather, red tide, travel issues, etc.). Cancellation requests must be submitted in writing by the registered guest—phone/text not accepted.brbrCity of Anna Maria Vacation Rental License: VR16-000537brMax Occupancy: 6 Guests | Max Vehicles: 2brInformation deemed reliable but not guaranteed; subject to change or withdrawal without notice.

Anna Maria Aloha – Beach Block Cottage, Steps to Gulf, Outdoor Living, Pet OK

Anna Maria, Florida, United States

Bed

Bath

Sleeps

$353.99

**Photos Updated April 2025**brThe Sea Spray Cottages are an adorable group of Units located in the North End of Anna Maria, West of Gulf Drive and only a few houses to the highly acclaimed Gulf Beach. brbrSea Spray 5 is a stand alone cottage with 3 Bedrooms and 2 Baths located at the front right of the property with its own private pool. Comfortable beachy furnishings and a full kitchen with Stainless Steel appliances. brbrThis property features a private driveway, a screened patio at the front of the home, and plenty of outdoor space to enjoy the Florida sunshine! This unit has its own washer and dryer located in just off of the kitchen. There is a flat screen TV in the living room and master bedroom. The master bedroom also has it own private ensuite bath. brbrYou will absolutely love the short stroll to the beach as well as the Island charm offered by this home.brbrPETS: Please note this property is NOT pet friendly. brbrPARKING: 2 cars maximum are able to park at this home. We ask our guests to please plan accordingly and coordinate with your group. There is no overnight parking available for additional vehicles.brbr***OVERCROWDING CONSEQUENCES***brMaximum occupancy of rental homes on Anna Maria Island are set by the Cities and are strictly enforced. An occupant is any person staying overnight, regardless of the number of nights. Due to recent issues of overcrowding in the area, if maximum occupancy is exceeded during your stay, a $1000 (one thousand dollar) overcrowding fee will be charged to the payment method on file and your party will be immediately evicted. We appreciate your understanding and cooperation to keep Anna Maria Island enjoyable for everyone.brbrYou are vacationing in a residential area. Please be a good neighbor by keeping the noise to a respectful level during the day and night. Excessive and unreasonable noise can deprive neighbors of the peaceful enjoyment of their private property.brbr*Exceeding the noise ordinance could result in disciplinary actions including fines and/or termination of your rental agreement without refund.

Sea Spray 5: *Heated Pool *Steps to beach *Close to shops and dining

Anna Maria, Florida, United States

Bed

Bath

Sleeps

$491.55

Purple Alamanda Unit A (Downstairs Unit) - 2 bedroom/1 bath Duplex on the North End of Anna Maria , Bean Point Beach less than 5 min walk brbrSet on the desired North End of Anna Maria Island, this fully remodeled coastal retreat is just steps from the pristine shoreline of Bean Point Beach—one of the island’s most exclusive and serene beaches.brbrThe duplex property features fully remodeled units thoughtfully arranged around a freestyle heated pool, creating a private, resort-style atmosphere. Guests may reserve a single unit or the entire property , total of 5 units available for rent in multiple duplexes making it ideal for extended families or refined group gatherings seeking both togetherness and privacy.brbrLocated in a low-traffic area, the neighborhood is ideal for biking around the island in a relaxed and safe setting. Guests can also enjoy easy transportation on the free Anna Maria Island trolley, which runs approximately every 20 minutes and offers multiple convenient stops throughout the island.brbrBicycle and golf cart rentals are readily available nearby, making it simple to explore at your own pace. A variety of restaurants, charming local shops, and the Publix supermarket are all within a 10-minute drive and are easily accessible by bike or golf cart, adding to the effortless island lifestyle.brbrPurple Alamanda Unit A offers a peaceful private patio, perfect for morning coffee or evening unwinding. brbrThe interior is fully remodeled and elegantly furnished with a relaxed yet elevated coastal aesthetic. brbr- Master Bedroom - one king bed br- 2nd bedroom -two twin beds br- Bathroom - Full bathroom with a walk-in shower with a rain shower head and handheld fixturebr- Fully equipped kitchen provides everything needed for effortless meal preparation during your stay.br- Living Room -an open, thoughtfully designed layout with a generous U-shaped sofa br- Dinning Area - a dining space that comfortably seats four, ideal for both relaxed lounging and casual island dining.brbrStep outside to lush tropical surroundings, where beautiful palms create a serene island atmosphere from the moment you arrive.brbr - A private back patio featuring a dining table with umbrella, perfect for enjoying morning coffee or relaxed outdoor meals.br- A propane BBQ grill is provided for convenient outdoor grilling ( by lower level car port and the pool area ) br- An outdoor heated pool with loungers is fully fenced and surrounded by tropical palms, creating a resort-style setting br- An outdoor shower is conveniently available to rinse off the sand after a day at the beach before enjoying a refreshing swim.br- A shaded tiki seating area offers the perfect place to relax and cool off after sunny island daysbr- Cornhole games add a fun, casual touch for friendly competition and laid-back afternoons.brbrOutdoors is surrounded by lush tropical landscaping and located just moments from the Gulf, this north-end escape delivers effortless island luxury—thoughtfully updated, quietly refined, and unmistakably Anna Maria.brbrbrMaximum Occupancy: 4 guests brParking: Limited to two vehicles (1 by the unit ,1 in guest parking) brbrExtras You’ll Love:brbrComplimentary High-speed Wi-Fi and Smart TVs for your entertainmentbrOn-site parking for conveniencebrProfessional Linen ServicesbrBeach Chairs, Beach Wagon, & Beach Umbrella provided brbrLinens and Amenities: - The starters included are the following: brbrPer Guest: 1 Bath Towel, 1 Hand Towel, 1 Washcloth, 1 Beach Towel , 1 Bath Mat per bath brPer Full Bathroom: 2 Rolls of Toilet Paper, Hand Soap, Starter size Shampoo, Conditioner, Body Wash , Cosmetic Cloth, Bath MatbrPer Kitchen: 1 Kitchen Towel and cloth , 1 Roll of Paper Towel, Dish Soap, Sponge, Dishwasher Pods-3 , Laundry Detergent, Garbage Bags -3brbrPools : Our pools are serviced weekly. Due to the tropical nature of the island , it is not unusual to find unexpected debris in the pool. Pool heaters will not operate if the outside temperatures get below 60F . There will be days when weather conditions will to allow pool heaters to accommodate swimming. No credit, discount, and /or rate adjustments can be granted for circumstances beyond our control.brbrCancellation Policy : br100% refund if cancelled 14 days before check-in; 50% refund if cancelled 7-14 days before check-in ( minus admin fee) , 0% if cancelled less than 7 days .brbrNoise Ordinance :brAnna Maria Island, Florida has a noise ordinance to maintain the tranquility of the island. The ordinance prohibits loud noises during quiet hours, which are from 10 PM to 8 AM every day. brWhat is prohibited brLoud music, including amplified instruments, Loud vehicle noises, Loud shouting, yelling, or screaming, Loudspeakers or other sound equipment for commercial advertising, Loud noises from animals.brbrTurtles: brTurtle season rules (May–October):br-No lights or flashes – avoid flashlights, phone flash, flash photography at night.br-Respect marked areas – don’t write on, step into, or tamper with flagged nests.br-Leave beaches clean & flat – remove all items, fill holes, flatten sandcastles.brbrShells : brAvoid taking any shells that have living organisms inside—if it's alive, leave it be.

BEST LOCATION! NORTH END OF ANNA MARIA, FL STEPS TO BEACH & DINING - LOWER UNIT

Anna Maria, Florida, United States

Bed

Bath

Sleeps

$1,632

The Willow Inn by Anna Maria Life Vacation Rentalsbr201 Willow Ave, Anna Maria, FL 34216brbrWhat You'll Love About This Home:brLocation - 1 Block to the Beach! Corner of Gulf & Willow!br4 Bedrooms / 4.5 Bathroomsbr3 King Beds, 2 Queen Beds with 2 Twin Upper Bunk BedsbrHeated Pool & SpabrIn Pool LoungersbrElevator (access to all 3 floors)brRoof Top Deck with Adirondack ChairsbrGas BBQ GrillbrLiving Room FireplacebrPutting GreenbrPool Side Adirondack Chairs & Pool LoungersbrOutdoor Verandah with Lounge FurniturebrPool Level Outdoor Dining Table for 8brPool Level Entertainment Area with Large TV, Lounge Furniture, Fireplace & Ping Pong TablebrProfessional Linen Service, Washer & DryerbrComplimentary WIFIbrBeach Towels, Beach Chairs, Beach WagonbrParking for 4 Vehiclesbr:brDetails:brLocated on the corner of Gulf & Willow, The Willow Inn is one block to the crystal-clear waters of the Gulf of Mexico! With gorgeous outdoor spaces, multiple balconies and living areas, our custom home has everything you need to vacation in style.brbrThe main living level of the home features a living room with a gas fireplace, gourmet kitchen, dining area and sliding glass doors to a balcony overlooking the tropical backyard and pool. A large kitchen island includes bar seating for four. Enjoy a meal at the dining room table which seats eight.brbrThis level also includes two king bedrooms with en-suite bathrooms. The master bedroom features a private balcony, oversized walk-in shower and free-standing bathtub. The second king bedroom also has a walk-in shower. The third level has a separate living area with a TV, wine chiller, and access to the roof top deck where you can relax in an Adirondack chair and take in a peaceful sunrise. The additional bedrooms on this level, one with a king bed and the other with two twins over two queen bunkbeds, have their own private en-suite bathroom. Each bedroom has a TV and includes crisp linens and plush towels from our professional linen company. Your guests will stay connected with complimentary WFI and enjoy all of the comforts of home, including a washer and dryer. The convenience of an elevator provides easy access to each level of the home.brbrOur sparkling, heated pool is one of the largest private pools on the island and is complete with a spa and in-pool loungers. You will love the putting green, poolside entertainment area with a ping pong table, fire place, large screen TV an cozy lounge seating. A gas grill and dining table for eight, lend to lovely dinners al fresco. An outdoor shower allows you to rinse the sand from your suit before entering the pool.brbrThe Willow Inn is easy walking distance to Gulf Ave, restaurants, and the free island trolley, which travels the entire length of the 7 miles of the island. Hop on and off at your leisure and explore shopping, dining and the beaches. The perfect location for your next beach vacation!brbrBedroom 1 - King Bed, Ensuite Bathroom, TV - Floor 2brBedroom 2 - King Bed, Ensuite Bathroom, TV - Floor 2brBedroom 3 - King Bed, Ensuite Bathroom, TV - Floor 2brBedroom 4 - 2 Sets of Twin over Queen Bunkbeds, Ensuite Bathroom, TV - Floor 3brbrPlease note:brPets are not allowed in this home.brAmenities are subject to change.brbrYou are vacationing in a residential area. Please be a good neighbor by keeping the noise to a respectful level during the day and night. Excessive and unreasonable noise can deprive neighbors of the peaceful enjoyment of their private property. The maximum occupancy is eight.brbrVR21-000076brbrGolf Cart DEAL ALERT!!! brReserve now a street legal GOLF CART from Fun & More Rentals! 4, 6 or 8 passenger gas or electric carts to choose.brFUN way to explore the island for the entire family.brMention Anna Maria Life Vacation Rentals and receive this VIP deal!brwww.FunAndMoreRentals.combr941-462-2719brbrIMPORTANT INFORMATION: brbrYour booking is with Anna Maria Life Vacation Rentals. We will send you check-in instructions 14 days prior to your arrival date. We will send you our rental agreement in an electronic signature document. Please review and return to us by following the instructions.brbr** Your signed rental agreement must be returned in order to receive your check-in details. brbrVRBO BOOKINGSbrbrAnna Maria Life Vacation Rentals will charge your credit card for your deposit payment. You will also see a separate charge by VRBO for their service fee. brbrYour final balance is due 60 days prior to your arrival date. We will send you a final payment reminder 90 days prior to arrival. We do not automatically charge your card for your final balance. brbrThe instructions for making your final payment will be included in your final payment reminder.brbrPlease review the cancellation policy prior to booking. brbrGOOGLE VACATION RENTAL BOOKINGSbrbrYour payment is due in full at the time of booking and the final balance information above does not apply to your reservation.

The Willow Inn: Huge Pool, Game Room, One Block to Beach by Anna Maria Life Vacation Rentals

Anna Maria, Florida, United States

Bed

Bath

Sleeps

$1225.46

Love Me Blue by Exclusive Vacations brVR24-000043 brbrWelcome to Love Me Blue, part of our Exclusive Collection. This luxury beach home offers four bedrooms, four and a half baths, located on the north end of Anna Maria Island! Just a three-minute walk to the serene Bean Point beach and one mile to the shops and restaurants of Pine Avenue, this stunning home combines resort-style amenities with elegant island living. Featuring a rooftop deck, private pool with a spa, and exclusive touches like a golf cart and luxury beach gear, Love Me Blue is the ultimate Gulf Coast getaway for families and groups.brbrHighlights br• 3-minute walk to Bean Point beach br• 4 Bedrooms / 4.5 Bathrooms br• 3 Kings, 2 Twins br• Rooftop deck with sunrise and sunset views br• Private pool with in-ground spa br• Ping pong, pool table, Connect 4, and Pac-Man br• Outdoor dining area and BBQ grill br• Dog friendly br• Electric vehicle charger br• Elevator access br• 4 Parking spots brbrExclusive Amenities: br• 6 Seat Club Car Cru Golf Cart br• Luxury Beach Bikes br• Luxury Beach Chairs and a Beach Cart br• Upgraded Bed and Bath Linens and Toiletries br• Portable Pack and Play brbrStep outside and dive into your private pool and spa, perfect for unwinding after beach days. The rooftop deck is ideal for taking in panoramic views of Anna Maria Island at sunrise or sunset. Challenge your friends and family to games of ping pong, pool, connect 4, or Pac-Man in the game area, and then gather for meals in the outdoor dining space. With fun, relaxation, and luxury at every turn. brbrInside, the open concept living area is filled with natural light and chic coastal décor. The spacious living room includes plush seating and a TV for family movie nights. The fully equipped modern kitchen features stainless steel appliances, a large island with seating, and a formal dining table where everyone can gather for memorable meals. brbrThe primary suite is a peaceful retreat with a king bed, private balcony, and ensuite bathroom with a double vanity and walk-in shower. The second bedroom also includes a king bed and ensuite bathroom with a shower and tub combo. The third bedroom features a king bed and ensuite walk-in shower, while the fourth bedroom has two twin beds and an ensuite bathroom with a walk-in shower. Each room is furnished with TVs, ample storage, and premium linens. brbrRoom Details br• Primary Bedroom: King bed, ensuite bathroom with double vanity and walk-in shower br• Second Bedroom: King bed, ensuite bathroom with shower/tub combo br• Third Bedroom: King bed, ensuite bathroom with walk-in shower br• Fourth Bedroom: Two Twin beds, ensuite bathroom with walk-in shower brbrThis home includes a washer and dryer, Wi-Fi, private parking, and an outdoor shower. Guests can enjoy multiple balconies with seating or entertainment in the game room. Guests will love the added luxuries that make this home truly special, including a 6 seat Club Car Cru golf cart, luxury beach bikes, and premium beach chairs with a beach cart for easy transport. Inside, you’ll find upgraded bed and bath linens, and a portable pack-and-play for families traveling with little ones. A dedicated EV charging outlet and residential elevator add modern convenience, while the home’s thoughtful design ensures comfort throughout. brbrNestled on the coveted north end of Anna Maria Island, Love Me Blue is just a short stroll to Bean Point, one of the island’s most picturesque beaches. Spend the day shelling, swimming, and watching dolphins before heading to Pine Avenue, just one mile away, for boutique shopping, fresh seafood, and ice cream parlors. With easy access to the Gulf waters, parks, and island attractions, this home places you close to everything Anna Maria has to offer. brbrLove Me Blue is a luxury retreat designed for families and groups seeking the perfect mix of fun, relaxation, and island elegance. Book your stay today and start making unforgettable memories! br brbr- brThis home is managed by AMI Locals, an Anna Maria Island property management company. brbrThis property allows dogs with host approval prior to arrival. Please note there will be an additional pet fee associated, see our AMI Locals Rental Policies for full details. brbr4 cars maximum are able to park at this home. We ask our guests to please plan accordingly and coordinate with your group. There is no overnight parking available for additional vehicles. brbrWe do not accept reservations from anyone under 25 years of age. We do not allow persons under 25 to occupy a property unless accompanied by someone over 25 years of age. Please see our AMI Locals Rental Policies for full details. brbrPlease Remember: You are vacationing in a residential area. Please be a good neighbor by keeping the noise to a respectful level during the day and night. Excessive and unreasonable noise can deprive neighbors of the peaceful enjoyment of their private property. *Exceeding the noise ordinance could result in disciplinary actions including fines and/or termination of your rental agreement without refund.

Rooftop Views! Pool, Spa and Game Room!

Anna Maria, Florida, United States

Bed

Bath

8

Sleeps

$641.31

Welcome to Hangin' on Hammock!brOn Anna Maria Island (Anna Maria, FL)brbrPlease Note: The pool and spa are currently under construction and are scheduled for completion by May 2026. Construction is set to begin January 1, 2026. Because the pool and spa are not yet available, reduced rates are being offered for stays now through the end of the year.brbrTucked along a quiet stretch on the north end of Anna Maria Island, this home blends easy island living with space to gather, unwind, and enjoy the water.brFresh paint, updated furniture, and bright interiors create a breezy coastal feel. Outside, a private saltwater pool and spa, outdoor kitchen, and dock invite long afternoons in the sun or peaceful mornings by the mangroves.brbrWalk to Pine Avenue's local shops and cafés or take a short stroll to the Gulf beaches to watch the sunset paint the sky.brbrPerfect for: families, couples traveling together, and small groups looking for a comfortable home base with room to play and relax.brbrHighlightsbr- Canalfront single-family home near Pine Avenue and the beachbr- 4 Bedrooms | 2 Full Bathroomsbr- Heated saltwater private pool & spa with outdoor kitchen and dining areabr- Game room with pool table, bar, and sleeper sofabr- Private dock on canal (not boat-accessible) — ideal for kayaking and fishingbr- 2 kayaks provided for guest usebr- Updated living spaces with new furnishings and décorbr- Fully equipped kitchen with island seatingbr- Driveway parking for up to 4 vehicles (no garage access)br- Pet-friendly with prior approvalbrbrInterior SpacesbrStep inside to an open, light-filled living area with vaulted ceilings and plenty of natural light. Comfortable seating and soft coastal tones make this the heart of the home — a place to gather, read, or share the stories of the day.brbrThe kitchen features modern appliances and an inviting island for easy meals or morning coffee. The dining area flows naturally into the living space, leading to porches at both the front and back of the home.brbrBedrooms are thoughtfully arranged for rest and privacy:br- Primary King Bedroom: En-suite bath and access to the front deck porch.br- King Bedroom: Also opens to the back porch for quiet mornings by the water.br- Queen Bedroom: Access to the shared back porch overlooking the canal.br- Twin Bedroom: Two twin beds, washer & dryer inside, accessed through the main hall bathroom.brbrLayout Overviewbr- Ground Level: Entryway and game room with pool table, bar, and sleeper sofa.br- Main Level: Open living, dining, and kitchen areas; hallway to bedrooms and baths; access to front and rear porches.br- Bedrooms: Three (king, queen, twin) open to the back porch; one primary king suite at the front with private bath and porch.br- Bathrooms: Two total — a full hall bath with tub/shower combo and the primary king en-suite bath.brbrOutdoor LivingbrStep outside to a peaceful backyard framed by mangroves and gentle water views.brbrTake a swim in the heated saltwater pool, relax in the spa, or fire up the outdoor kitchen for dinner on the patio. The spacious dining area and loungers make it easy to spend the whole day outdoors.brbrThe private dock offers a quiet place to cast a line, launch one of the provided kayaks, or simply enjoy the rhythm of island life.brbrWhether sipping morning coffee on the porch or grilling by the water at dusk, this home invites you to slow down and stay awhile.brbrKitchen & DiningbrDesigned for both function and connection, the kitchen includes:br- Stove, oven, and microwavebr- Refrigerator/freezer with ice makerbr- Dishwasher and garbage disposalbr- 12-cup coffeemaker, blender, and toasterbr- Cookware, utensils, and dinnerwarebr- Island seating for casual dining or conversationbrbrThe adjoining dining area comfortably seats the whole group for shared meals and family game nights.brbrAdditional Amenitiesbr- Air conditioning and heatbr- Cable television and high-speed Wi-Fibr- Washer and dryerbr- Linens, bath towels, and beach towels (professionally laundered)br- Hair dryer, iron, and ironing boardbr- Beach gear rental credit (chairs, umbrellas, carts — details provided after booking)br- Sleeper sofabrbrParkingbr- Driveway parking for up to 4 vehiclesbr- No garage accessbrbrGuest Accessbr- Guests have private access to the entire home, pool, spa, dock, and outdoor spaces.br- Check-in is direct and contactless — arrival details and a personalized access code are shared before your stay.brbrPoliciesbrbrPlease Remember: You are vacationing in a residential area. Please be a good neighbor by keeping the noise to a respectful level during the day and night. Excessive and unreasonable noise can deprive neighbors of the peaceful enjoyment of their private property. *Exceeding the noise ordinance could result in disciplinary actions including fines and/or termination of your rental agreement without refund.brbrNO SMOKING.brbrPets are welcome with prior approval, provided they meet our pet policy guidelines. We allow a maximum of two pets, each weighing under 65 lbs. A pet fee applies based on the length of your stay: $100 for stays under 4 days, $200 for stays of 4-14 days, and $400 for stays of 15+ days, per pet.brbrBooking & Fee PolicybrInclude all guests and pets in your reservation request for accurate pricing. Additional fees apply for extra occupancy (over 2 guests per bedroom) or undeclared pets.brbrOptional Services (subject to approval)brEarly check-in/late departure, elevator access, and mid-stay cleaning for stays of 28+ days. Fees for approved add-ons are collected after booking.brbrReservations & Guest RequirementsbrMost stays are 7 nights, Saturday–Saturday, though flexible dates may be available outside peak/holiday weeks—confirm before booking, as changes are not always possible afterward. Guests must be 25+, provide valid ID, and remain for the full stay. Standard occupancy is 2 per bedroom; extra guests are $25/person/night up to the maximum allowed.brbrQuiet Hoursbr10 PM–8 AM. Maintain reasonable noise at all times to respect neighbors; excessive noise is not permitted.brbrCleaning & LinensbrHome is professionally cleaned and sanitized between stays. Starter amenities provided; daily service available for a fee. Stays of 28+ days require a mid-stay clean. Linens/towels are commercially laundered through our Professional Linen Program; no extra sets stored onsite.brbrGolf Cart RentalsbrExplore the island with ease! After booking, reserve a golf cart through our sister company, Once Upon A Beach Carts, and enjoy an exclusive discount available only to our vacation rental guests.brbrPool & SpabrPool heated year-round to 82–85°F; heating may be affected by cooler weather. Heaters/filters off during quiet hours (10 PM–8 AM). Spa, if available, is part of the pool, seasonal, not a commercial hot tub, and may be unavailable in summer. Guests may not adjust equipment; violations may result in fines or damages.brbrProperty SecuritybrExterior cameras may monitor entries, driveways, pool equipment, and backyard access for security, deliveries, and occupancy compliance. Cameras do not face private areas.brbrPayments & Cancellation PolicybrPolicies updated October 6, 2025 — see full Terms & Conditions for details.brbrPayment SchedulebrDepositbr- Reservations up to 20 days: 50% of total amount due at time of booking.brRemaining Balancebr- Reservations up to 20 days: Remaining 50% due 30 days prior to check-in.brbrCancellation PolicybrFor Reservations of 20 Days or Lessbr- More than 30 days before arrival: Full refund of deposit (including taxes) minus non-refundable booking administration fee.br- 14–29 days before arrival: Refund of 50% of total rental, fees, and taxes, minus non-refundable booking administration fee.br- Less than 14 days before arrival: Refunds only for base rental rate, fees, and taxes for nights we are able to rebook, minus non-refundable booking administration fee.br- Please note: While we make every effort to rebook, we cannot guarantee the same rate or number of nights. For any nights that cannot be re-rented, as well as for non-arrivals, late arrivals, early departures, or alterations resulting in lost revenue, no refunds or price adjustments will be made.brbrTravel InsurancebrCSA Travel Insurance is available to U.S. guests (except NY and HI residents) and is strongly encouraged to protect your trip from unforeseen events. No refunds are given for COVID-19, weather, or beach conditions outside our cancellation policy. Hurricane season runs June 1–Nov 30; insurance can safeguard your plans. In the event of a mandatory evacuation, home unavailability, or government order halting vacation rentals, guests receive a full refund of base rate, applicable fees (minus booking fee), and taxes.brbrAdditional TermsbrNo refunds for events beyond our control (weather, red tide, travel issues, etc.). Cancellation requests must be submitted in writing by the registered guest—phone/text not accepted.brbrCity of Anna Maria Vacation Rental License: VRC24-000039brMax Occupancy: 8 Guests | Max Vehicles: 4brInformation deemed reliable but not guaranteed; subject to change or withdrawal without notice.

Hangin' on Hammock – Canalfront Pool Home with Spa, Dock & Game Room Near Pine Avenue

Anna Maria, Florida, United States

Bed

Bath

Sleeps

$1293.69

Sail Away by AMI Locals brVR19-000048 brbrWelcome to Sail Away, a spectacular six bedroom, six and a half bath canal-front luxury home in the heart of Anna Maria Island. With a private dock, a resort style pool with a swim up bar, and a rooftop deck showcasing stunning island views, this vacation rental is designed for unforgettable gatherings with family and friends. Just a short walk from the beautiful beaches of Anna Maria and Pine Avenue’s boutique shops and waterfront dining, Sail Away offers the perfect blend of relaxation and island adventure. brbrHighlights br• Canal front with private dock (fits up to 19ft boat) br• 8-minute walk to Anna Maria beach br• 6 Bedroom / 6.5 Bath br• 5 King beds, 1 Twin-over-Twin bunk bed br• Private pool with in-ground spa and swim-up bar br• Rooftop deck with sweeping island views br• Game room with pool, ping pong, and foosball tables br• Elevator access br• BBQ grill and outdoor shower br• 4 Parking spaces brbrThe backyard is an island oasis with a sparkling pool featuring a sun shelf and swim up bar, a relaxing spa, and a sunken fire pit perfect for evening gatherings. Lounge in the Florida sunshine, fire up the BBQ grill for outdoor dining, or catch the big game on the outdoor bar’s mounted TV. Boaters will love the private dock, able to accommodate boats up to 19 ft, while the rooftop deck offers panoramic views of Anna Maria Island’s turquoise waters and vibrant sunsets. brbrInside, the open concept living room invites you to unwind with plush seating, a large TV, and an elegant electric fireplace. A decorative wine cellar adds a touch of sophistication, while the gourmet kitchen is equipped with a six burner stove, double ovens, premium appliances, and a massive island that makes group cooking a breeze. The dining area offers a spacious setup for group meals and additional seating at the bar for larger gatherings, providing flexible dining options for everyone. Upstairs, a second living space with a wine fridge, TV, and access to the rooftop deck provides an additional spot to relax and entertain. brbrThe third-floor primary suite is a showstopper, complete with balcony access, a spacious walk-in closet, and a spa-like ensuite bathroom featuring a soaking tub, walk-in shower, and double vanity. The second suite, also on the third floor, offers a king bed, balcony views, and a luxurious ensuite bathroom. Three more king bedrooms on the second floor each feature their own ensuite baths and balconies, while the bunk room is a nautical retreat with twin-over-twin beds and a shower/tub combo. brbrRoom Details br• Primary Bedroom, 3rd floor: King bed, balcony, walk-in closet, ensuite bathroom with soaking tub and walk-in shower br• Second Bedroom, 3rd floor: King bed, balcony, ensuite bathroom with walk-in shower br• Third Bedroom, 2nd floor: King bed, balcony, ensuite bathroom with walk-in shower br• Fourth Bedroom, 2nd floor: King bed, balcony, ensuite bathroom with walk-in shower br• Fifth Bedroom, 2nd floor: King bed, ensuite bathroom with walk-in shower br• Sixth Bedroom, 2nd floor: Twin-over-Twin bunk bed, ensuite bathroom with shower/tub combo brbrFor added convenience, Sail Away includes an elevator, washer and dryer, and a game room with a pool table, foosball, and ping pong. Beach days are a breeze with easy access to Anna Maria’s beach, and nearby Pine Avenue offers charming shops, restaurants, and ice cream stops to enjoy after a day in the sun. brbrSail Away is the ultimate island retreat for families, groups, or travelers seeking luxury, space, and fun. Reserve your stay today and start planning your perfect getaway! br br- brNo pets are allowed in this property. brbr4 cars maximum are able to park at this home. One of the garages is locked as owner’s storage. We ask our guests to please plan accordingly and coordinate with your group. There is no overnight parking available for additional vehicles. brbrThis home is managed by AMI Locals, an Anna Maria Island property management company. brbrThese premises are monitored by video surveillance in select exterior areas. brbrWe do not accept reservations from anyone under 25 years of age. We do not allow persons under 25 to occupy a property unless accompanied by someone over 25 years of age. brbrPlease see our AMI Locals Rental Policies for full details. brbr Please Remember: You are vacationing in a residential area. Please be a good neighbor by keeping the noise to a respectful level during the day and night. Excessive and unreasonable noise can deprive neighbors of the peaceful enjoyment of their private property. *Exceeding the noise ordinance could result in disciplinary actions including fines and/or termination of your rental agreement without refund.

Island Escape! Pool, Spa, Ping Pong and Fire Pit for Group Fun

Anna Maria, Florida, United States

Bed

Bath

Sleeps

$798.68

Welcome to The Sand Castle located just a few steps from the Gulf beaches of Anna Maria Island. Built in 1924, the Castle is one of the oldest homes on the island. While it was lovingly restored in 2015, the history of the home can still be seen. The Sand Castle is a 4 bedroom, 3 and a half bath with the back patio surrounded by tropical landscaping where you can enjoy the heated pool, outdoor shower and Weber grill.brbrAs you enter in the home through the screened in porch, you will be in the stone turret with the staircase to the left and to the right the traditional dining room with seating for 8. The fully equipped vintage inspired kitchen is located off of the dining room. Straight through the entry way is the cozy living area with an electric fireplace and access to the screened in porch. Located off of the living area is the master suite with a comfortable king bed complete with 600 thread count prima cotton wrinkle free sheets and access to the side patio. The master bath is has a time inspired claw foot tub, walk in shower and double vanity.brbrUp the spiral staircase you will find three bedrooms. One complete with a queen sized bed and full bathroom. The second bedroom complete with 2 queen sized beds. The third bedroom complete with a queen bed as well. In the hallway you will find the mini coffee bar and access to the porch with a great view of the back patio. Located off that same hallway is the last full bathroom.brbrLinens, towels, beach towels, beach wagon, chairs and umbrella is provided in this home.brbrLizzie Lu's Island Retreat is a full-service property manager on Anna Maria Island to ensure our guests enjoy some of the nicest, well stocked homes on the island. For an additional charge, we offer GEM cars among other services. Rest assured we are here to assist as needed in the most efficient manner possible. While vacationing on Anna Maria Island, please adhere to our local rules and regulations for our residential community which are included in our homes as well as our arrival information.

Historic 1924 Luxury Beach Home with Large Heated Pool 3 Houses to Beach

Anna Maria, Florida, United States

Bed

Bath

Sleeps

$552.09

Welcome to Shady Mango! An inviting ground-level vacation home just three blocks from the beach! With two bedrooms and two bathrooms, this rental sleeps up to six guests. You and your guests can sit back, relax, watch movies, and connect over effortless conversations in the living area. The fully equipped kitchen has ample counter space, making meal prep a breeze. Delight in your delicious island-inspired homemade and Anna Maria Island take-out at the indoor table or outside at the dining table, where you can also enjoy the island breeze. There is an electric fireplace in the house for guest use. br br The primary bedroom offers a calming atmosphere perfect for catching up on much-needed sleep and has a tv for late-night entertainment. The second bedroom is perfect for another couple and has plenty of closet space for vacation attire and beach necessities. The primary bedroom has a bathroom which features a stand-alone tub. The guest bathroom has a walk-in shower.br br Relax in your private huge backyard oasis, where you and your guests can make a splash in the pool, soothe your muscles in the spa, and relax on one of the many lounge chairs. There is a BBQ grill perfect for grilling locally caught seafood. Explore the beautiful beaches Anna Maria Island offers, swim in the warm turquoise waters, and feel the sugary sand cover your feet. Afterward, browse the fantastic boutiques along famous, historic Pine Ave or head to any local restaurants for delicious treats and fresh seafood! Hop on the free trolley and explore the Island! Anna Maria Island has many guided tours. Kayak or paddleboard the Bay and the calm Gulf of Mexico, where you might even encounter some wildlife!br br HIGHLIGHTSbr br 1080 sq. ft. br Private Pool (26x14 ft.) and spabr Outdoor Showerbr Anna Maria - Pine Avenuebr Fireplace - electricbr 0.1 mile from bay access br 0.2 miles from beach accessbr br BEDROOMSbr br Sleeps 6br Primary Bedroom: Kingbr Second Bedroom: Queenbr Closed porch: Twin/Trundlebr br BATHROOMbr br Primary Bathroom: Claw-foot Tubbr Second Bathroom: Walk-in Showerbr br EXTERIORbr br After a long day at the beach, head back to Shady Mango and take advantage of its beautiful outdoor scape. Enjoy the outdoor shower to rinse off any sand and then take a dip in the crystal-clear private heated pool and large spa. There is a gas grill and multiple outdoor dining spots to enjoy a bite to eat in a beautiful, tropical landscape.br br The pool heat is $150.00 a week. Pool heaters in private homes are locked for your safety and controls must not be tampered with as they are monitored by the pool company. 86 F is the highest heat temperature setting which might not be always reached. Please note if cold days and nights occur, water temperatures will drop and may stay cooler longer. Pool heaters will not operate and will automatically shut down if outside temperatures get too cold. While we take every precaution to ensure that pools are heated as specified, weather conditions may affect the temperature of the pool. Nothing can be done about this issue. Outdoor spas are not hot tubs and require heat at the additional cost. The temperature of a spa is typically set at the same temperature as the pool. In the event of pool equipment malfunction during your stay, Duncan Real Estate will expedite repairs as quickly as possible. It may be necessary to close swimming pools for maintenance purposes. No refund or rent adjustment will be made for circumstances beyond our control, malfunctions, or loss of use of equipment or amenities. br br There are parking spaces for two cars at Shady Mango.br br Please keep in mind that you are vacationing in a residential area. Please be a good neighbor by keeping the noise to a respectful level during the day and night. Excessive and unreasonable noise can deprive neighbors of the peaceful enjoyment of their private property.br Amenities Include:br - Bedroom 1 Kingbr - Bedroom 2 Queenbr - Extra Beds Twin/Trundlebr - Bathroom 1 Claw-foot Tubbr - Bathroom 2 Walk-in Showerbr - Hot Waterbr - Ground Level Ybr - Central A Cbr - Cental Heatbr - Sqft under a c 1080br - Free Parkingbr - Parking Spots 2br - Self Check Inbr - Keyless Entrybr - Bath Towelsbr - Beach Towelsbr - Quality Linensbr - Hair Dryerbr - Hangersbr - Refrigeratorbr - Stovebr - Cookwarebr - Toasterbr - Blenderbr - Drip Coffee makerbr - Dishwasherbr - Microwavebr - Dining Tablebr - High Speed WIFIbr - TV 3br - Cable Channelsbr - Washerbr - Dryerbr - Ironbr - Ironing Boardbr - Cleaning Kitbr - First Aid Kitbr - Fire Extinguisherbr - Smoke Alarmbr - Private Pool Ybr - Pool Dimensions 26x14br - Spabr - Sun Loungersbr - Patiobr - Outdoor Diningbr - Propane Grillbr - Fire Pitbr - Board Gamesbr - Outdoor gamesbr - Exterior Outletbr - Mold Free Certificatebr - Duncan Emerald Club

Shady Mango by Duncan Real Estate

Anna Maria, Florida, United States

Bed

Bath

Sleeps

$412.39

Welcome to your perfect Anna Maria Island getaway! This highly rated home offers a private retreat with one of the larger pools on the island, a beautifully landscaped backyard, and a 20' tall tiki hut - hand-built by Native Americans - featuring a bar and seating for six. Lounge by the spa, play poolside games, or fire up the grill on one of two spacious decks with outdoor dining. brbrInside, you'll find quality furnishings, a large master suite with a king bed, a whimsical guest room with queen bed, and nook in the living room with a twin over twin bunkbed. The spacious family and game rooms, plus a dining area for six, provide plenty of room to relax. Enjoy smart TVs, games, books, and more for entertainment. brbrThis prime North End location means you’re just a short walk from the island’s best experiences. Stroll to the bay beaches, take the secret path shortcut out the back gate to North Bay Park, or enjoy fresh seafood at the nearby restaurants. The famous Gulf beaches, City Pier, and charming Pine Avenue shops are all within a 10-minute walk, while the free island trolley makes exploring even easier. Whether you're dolphin-watching, spotting wild parrots, or collecting sand dollars on the shore, nature lovers will be in paradise.brbrWith its unbeatable location and top-notch amenities, this home is the perfect island escape. Book now and make unforgettable memories!brbrBEACH GEAR: 4 beach chairs with shades, cooler and beach wagon.brbrPETS: Dogs are allowed with prior approval. Must be well trained and less than 40lbs. 2 dogs max. A $150 non-refundable pet fee applies per pet.brbrPARKING: 2 cars maximum are able to park at this home. We ask our guests to please plan accordingly and coordinate with your group. There is no overnight parking available for additional vehicles.brbr***OVERCROWDING CONSEQUENCES***brMaximum occupancy of rental homes on Anna Maria Island are set by the Cities and are strictly enforced. An occupant is any person staying overnight, regardless of the number of nights. Due to recent issues of overcrowding in the area, if maximum occupancy is exceeded during your stay, a $1000 (one thousand dollar) overcrowding fee will be charged to the payment method on file and your party will be immediately evicted. We appreciate your understanding and cooperation to keep Anna Maria Island enjoyable for everyone.brbrYou are vacationing in a residential area. Please be a good neighbor by keeping the noise to a respectful level during the day and night. Excessive and unreasonable noise can deprive neighbors of the peaceful enjoyment of their private property.brbr*Exceeding the noise ordinance could result in disciplinary actions including fines and/or termination of your rental agreement without refund.

Sassy Seahorse: Heated pool, hot tub, ping pong, Foosball and pool table!

Anna Maria, Florida, United States

Bed

Bath

Sleeps

$1199.04

Hip Nautic by AMI Locals brVR22-000090 brbrWelcome to Hip Nautic, a luxury four bedroom, four and a half bath beach retreat just steps from the beautiful bayside shores of Anna Maria Island. Perfectly situated near Pine Avenue’s shopping and dining, this modern, pet-friendly home offers upscale amenities including a private pool and spa, rooftop deck with bay views, and elevator access. Designed for families and groups seeking the ultimate island getaway, Hip Nautic combines coastal elegance and comfort for an unforgettable stay. brbrHighlights br• 4-minute walk to Bean Point Beach br• 4 Bedrooms / 4.5 Bathrooms br• 2 Kings, 1 Queen, 1 Twin-over-Full bunk br• Rooftop deck with water views br• Private pool and in-ground spa br• Elevator br• Dog friendly (with approval and additional fee) br• Ping pong table br• 3 parking spaces br• Near Pine Avenue shops and dining brbrThe outdoor living area is designed for relaxation and entertainment. Unwind beside the private heated pool and spa, soak up the sun from the loungers, or fire up the BBQ grill for a family cookout beneath the shaded outdoor dining area. The spacious rooftop deck is a true showstopper, perfect for morning coffee, sunset cocktails, or stargazing under the island sky. Every corner of Hip Nautic has been curated to make your stay effortless, stylish, and serene. brbrStep inside to discover modern coastal sophistication. The open main living area features floor to ceiling windows framing tranquil water views and filling the space with natural light. The gourmet kitchen is fully equipped with stainless steel appliances, a wine fridge, quartz countertops, and an elegant waterfall island with seating; ideal for preparing fresh island meals. Enjoy family breakfasts in the custom built-in breakfast nook or gather in the bright, comfortable living room with a plush sectional and TV for movie nights. brbrEach bedroom at Hip Nautic offers relaxing, spa-like comfort with luxury linens, soft lighting, and ensuite bathrooms. The primary suite on the third floor features a king bed, private balcony overlooking the bay, and an ensuite bathroom with a free-standing soaking tub and walk-in shower. brThe second bedroom has a king bed and ensuite bathroom with a walk-in shower, while the third bedroom offers a queen bed and its own ensuite. The fourth bedroom is ideal for younger guests, with a twin-over-full bunk bed and an ensuite bathroom with a tub-shower combination. brbrRoom Details br-Primary Bedroom (3rd Floor): King bed, balcony, ensuite bathroom with standalone tub and walk-in shower br-Second Bedroom (2nd Floor): King bed, ensuite bathroom with walk-in shower br-Third Bedroom (2nd Floor): Queen bed, ensuite bathroom with walk-in shower br-Fourth Bedroom (2nd Floor): Twin-over-Full bunk, ensuite bathroom with shower-tub combination brbrGuests will appreciate simple extras like Wi-Fi, washer and dryer, elevator access, and ping pong table. From Hip Nautic, it’s a short walk to the bayside beaches, Bean Point, Bayfront Park, and the charming shops and restaurants of Pine Avenue. Rent a kayak or paddleboard, explore nearby Gulf waters, or take the Anna Maria Island trolley to discover more of the island’s hidden gems. brbrWhether you’re seeking a family-friendly coastal getaway or a stylish luxury escape, Hip Nautic by AMI Locals delivers an exceptional Anna Maria Island vacation rental experience. Enjoy breathtaking views, modern design, and all the comforts of home just steps from the beach. brbrBook your stay at Hip Nautic by AMI Locals today and start making unforgettable island memories! brbr- brThis home is managed by AMI Locals, an Anna Maria Island property management company. brbrWith host approval before check-in, this property accepts dogs only (No cats or other animals are allowed). An additional pet fee will apply. See our AMI Locals Rental Policies for full details. brbr3 cars maximum can park at this home. We ask our guests to please plan accordingly and coordinate with your group. There is no overnight parking available for additional vehicles. brbrWe do not accept reservations from anyone under 25 years of age. We do not allow persons under 25 to occupy a property unless accompanied by someone over 25 years of age. Please see our AMI Locals Rental Policies for full details. brbrPlease Remember: You are vacationing in a residential area. Please be a good neighbor by keeping the noise to a respectful level during the day and night. Excessive and unreasonable noise can deprive neighbors of the peaceful enjoyment of their private property. *Exceeding the noise ordinance could result in disciplinary actions including fines and/or termination of your rental agreement without refund.

Luxury Beach Retreat with Rooftop Deck and Pool in Anna Maria! - Hip Nautic

Anna Maria, Florida, United States

Bed