Vacation Rentals By Owner In Anna Maria, FL

$1565.8

Coastal Elegance! Pool, Putting Green, Movie Room, and More!

Anna Maria, Florida, United States

Periwinkle Place by Exclusive Vacations brVR25-000004 brbrIndulge in the ultimate luxury beach home at Periwinkle Place, part of our Exclusive Collection. This stunning estate in the heart of Anna Maria offers six spacious bedrooms and six and a half bathrooms. Just a five-minute walk from the pristine shoreline and steps from the shops and dining on Pine Avenue, Periwinkle Place combines coastal style with upscale amenities, including a pool with hot tub, private dock, golf cart, a private movie room and more, for an unforgettable beach vacation! Perfect for large families, retreats, or multi-generational gatherings, this home combines sophistication, comfort, and endless outdoor entertainment for your perfect stand getaway. brbrHighlights br• 5-minute walk to Anna Maria Beach br• 6 Bedrooms / 6.5 Bathrooms br• 5 Kings, 2 Twins/ Queen bunks br• Private Dock br• Private Pool with hot tubbr• Outdoor Kitchen br• Private Movie Room br• Putting Green br• Elevator access to all floors br• Short walk to Pine Avenue shops and dining br• Pet-friendly with approvalbrbrExclusive Amenities br• 6 Seat Club Car Cru Golf Cart for Guest Use br• Luxury Beach Bikes for Guest Use br• Beach Chairs and a Beach Cart for Guest Use br• Upgraded Bed and Bath Linens and Toiletries br• Portable Pack and Play br brExperience outdoor luxury with a private pool with hot tub, putting green, and lush tropical landscaping creating your own backyard paradise. The outdoor kitchen and BBQ grill make outdoor entertaining easy, while scenic balconies and a rooftop deck offer breathtaking views of the Gulf and surrounding water. Explore local water sports, fish from your private dock, or return after a day at the beach for a relaxing dip or sunset drinks. brbrStep inside this modern estate and be greeted by a seamless open-concept design. The elegant living room invites relaxation with plush seating, a large TV, and stylish decor, perfect for movie nights or unwinding in style. The gourmet kitchen boasts premium appliances, expansive countertops, and plenty of space for culinary creations, ideal for entertaining. The sophisticated dining area, seating eight comfortably, makes every meal a memorable occasion. br brRetreat to one of six luxurious bedrooms, each offering a tranquil sanctuary. The primary suite features a lavish king bed, a walk-in closet, and an ensuite with a double vanity, spacious walk-in shower, and a spa-like soaking tub. The remaining five bedrooms, all with plush decor, feature four king beds and one bunk room with two twins-over-a queen bed, each with ensuite bathrooms and walk-in showers to ensure privacy and comfort for everyone. The home also includes a half bath and an additional washer and dryer for convenience. brbrRoom Details br• Primary Bedroom: King bed, ensuite with walk-in shower and double vanity  br• Second Bedroom: King bed, ensuite with walk-in shower  br• Third Bedroom: Two Twins-over-a Queen bunk bed and ensuite bathroom br• Fourth Bedroom: King bed, ensuite with walk-in shower  br• Fifth Bedroom: King bed, ensuite with walk-in shower  br• Sixth Bedroom: King bed, ensuite with walk-in shower  br brBook Periwinkle Place today and enjoy an escape filled with water views, outdoor entertainment, and luxurious comforts. Perfect for family reunions, groups, or those seeking a stylish retreat, this home blends island charm with modern luxury. Reserve your dates now and start creating lifelong memories on Anna Maria Island! br 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 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. brbrUse of the provided golf cart requires the driver to maintain a current U.S. automobile insurance. Proof of insurance is required upon request.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.

7

Bed

6

Bath

8

Sleeps

$728.93

/ Nightly

Private Vacation Home

Chilli Fish by Duncan Real Estate

Anna Maria, Florida, United States

Chilli Fish offers the best of island living on the North end of Anna Maria Island. This gorgeous home features 4 bedrooms, 3 baths with a private pool and is just a short stroll to the white sandy beaches. There is plenty of room to host 8 guests. brbrEnter the home and get greeted by wonderful beachy decor and wide plank flooring and beautiful area rugs. brbrThis Island home offers a comfortable living area with plenty of seating, a dining area and a stunning renovated open kitchen area. There is also a full laundry room inside the house. Get to know the Island and explore its little side streets or take the easily accessible free Island trolley!brbrThe ground level floor plan makes it easy to take advantage of the backyard. The pool area is very inviting with the sun on it throughout the day and provides total privacy with mature palm trees. brbrHIGHLIGHTSbrbr1,900 sq. ft. brbrPool deck spacebrbrPrivate poolbrbrLuxury Rental brbr0.2 miles from bay access brbr0.4 miles from beach accessbrbrBEDROOMSbrbrSleeps 8brbrPrimary Bedroom: King EnsuitebrbrSecond Bedroom: King Ensuite brbrThird Bedroom: Queen Ensuite brbrFourth Bedroom: 2 x FullbrbrBATHROOMSbrbrPrimary Bathroom: Walk-in ShowerbrbrSecond Bathroom: Walk-in ShowerbrbrThird Bathroom: Shower/Tub Combo brbrEXTERIORbrbrRelax in the pool after your day at the beach. Enjoy evening cocktails in the covered patio area with the outdoor big screen TV for watching your favorite games or cook up fresh seafood on the grill and dine alfresco. This is Island style living at its best.brbrThe 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. brbrThere are four designated parking spaces in the driveway for this property. 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 Kingbrbr- Bedroom 2 Kingbrbr- Bedroom 3 Queenbrbr- Bedroom 4 2 Fullbrbr- Hot Waterbrbr- Beach Access 0.4 milesbrbr- Bay Access 0.2 milesbrbr- Ground Levelbrbr- Central A Cbrbr- Cental Heatbrbr- Sqft under a c 1650brbr- Parking Spots 4brbr- Front Security Camerabrbr- Keyless Entrybrbr- Bath Towelsbrbr- Beach Towelsbrbr- Quality Linensbrbr- Hair Dryerbrbr- Hangersbrbr- Refrigeratorbrbr- Ice Makerbrbr- Stovebrbr- Ovenbrbr- Cookwarebrbr- Toasterbrbr- Blenderbrbr- Keurigbrbr- Drip Coffee makerbrbr- Dishwasherbrbr- Microwavebrbr- Garbage Disposalbrbr- Dining Tablebrbr- High Speed WIFIbrbr- TV Streaming Onlybrbr- Washerbrbr- Dryerbrbr- Ironbrbr- Ironing Boardbrbr- Cleaning Kitbrbr- Fire Extinguisherbrbr- Smoke Alarmbrbr- Carbon Monoxide Alarmbrbr- Private Pool Ybrbr- Pool Alarmsbrbr- Sun Loungersbrbr- Patiobrbr- Propane Grillbrbr- Beach Amenitiesbrbr- Board Gamesbrbr- Duncan Emerald Clubbrbr

Bed

Bath

Sleeps

$522.66

/ Nightly

Private Vacation Home

Chardonnay Shores - Beautiful 2 Bedroom Home

Anna Maria, Fl, United States

Chardonnay Shores by Anna Maria Island AccommodationsbrbrWelcome to Chardonnay Shores, a beautifully refreshed three-bedroom, two-bath Anna Maria Island vacation rental located in the heart of Anna Maria City, just a short stroll from the sugar-white sands of Anna Maria City Beach and the charming shops and restaurants of Pine Avenue. This stunning home has undergone a major renovation and now feels like an entirely new coastal retreat. Designed for families and groups looking for the perfect island getaway, Chardonnay Shores combines stylish interiors, fun-filled outdoor spaces, and a fantastic location close to everything that makes Anna Maria Island unforgettable.brbrHighlightsbr• Recently renovated upscale home br• 3 Bedrooms / 2 Bathrooms br• 2 Kings, 1 Twin over Full Bunk, 1 Queen Sleeper Sofa br• Private heated pool br• Converted garage game room br• Movie screen, ping pong, shuffleboard, and Connect 4 br• Newly turfed backyard with putting green br• Two outdoor showers br• Family friendly island retreat br• Convenient location near Pine Avenue shopping and dining br• 4 parking spaces brbrStep outside and discover your own private island escape designed for both relaxation and fun. The newly turfed backyard creates a fresh, clean outdoor space perfect for gathering with family and friends after a beach day. Practice your short game on the private putting green, rinse off the sand with two convenient outdoor showers, or unwind under the Florida sunshine with plenty of room to lounge and play. brbrThe converted garage game room is one of Chardonnay Shores’ standout features, offering endless entertainment for guests of all ages. Challenge the family to ping pong, shuffleboard, or Connect 4, then settle in for a movie night with the large projector screen for the ultimate vacation hangout space. Whether you're enjoying sunny afternoons outside or game nights indoors, this home is built for making memories. Inside, Chardonnay Shores offers a bright and welcoming open layout with fresh coastal finishes and comfortable spaces designed for easy vacation living. The living room features plush seating and a queen sleeper sofa, creating the perfect place to gather for movie nights, morning coffee, or planning your next beach adventure. Large windows bring in natural light and add to the airy island feel throughout the home.brbrThe kitchen is beautifully updated and fully equipped with everything needed for preparing family meals, from quick breakfasts before the beach to evening dinners after sunset walks on the shore. Ample counter space, modern appliances, and a nearby dining area make entertaining effortless while keeping everyone connected.brThe primary bedroom is a peaceful retreat featuring a king bed, soft linens, and a private ensuite bathroom with a walk-in shower. This relaxing space is designed to help guests unwind after long days spent exploring Anna Maria Island, with plenty of room for luggage and a calm coastal atmosphere.brbrThe second bedroom also offers a king bed, making it ideal for another couple or additional guests seeking comfort and privacy. The third bedroom is perfect for kids or flexible group sleeping arrangements, featuring a twin over full bunk bed that adds both function and fun to the space. These guest rooms share a conveniently located hallway bathroom with a shower and tub combination, ideal for families returning from beach days and outdoor adventures.brbrRoom Detailsbr• Primary Bedroom: King bed and ensuite bathroom with walk-in shower br• Second Bedroom: King bed br• Third Bedroom: Twin over Full Bunk br• Hall Bathroom: Shower and tub combination br• Bonus: Queen Sleeper Sofa in living room brbrChardonnay Shores includes thoughtful extras that make your stay even more convenient, including a washer and dryer, outdoor showers for rinsing off after the beach, and a spacious layout that allows everyone to spread out comfortably. Its prime Anna Maria location places you just minutes from local boutiques, waterfront dining, and the beloved Pine Avenue district, where guests can enjoy shopping, ice cream stops, and sunset strolls.brbrChardonnay Shores by Anna Maria Island Accommodations is the perfect blend of comfort, style, and location for your next Anna Maria Island vacation. With a beautifully renovated interior, exciting game room, private putting green, and close proximity to the beach and Pine Avenue, this home offers everything you need for an unforgettable stay. Book your getaway today and start making memories in paradise.brbr-brThis home is managed by Anna Maria Island Accommodations, an Anna Maria Island property management company.brbrThis property does not allow pets of any kind. brbrThis property has an active Ring doorbell at the entrance. 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 Anna Maria Island Accommodations 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.

Bed

Bath

Sleeps

$3445.6

/ Nightly

Private Vacation Home

Luxury Beachfront on the Sand of Gulf of Mexico

Anna Maria, Florida, United States

Photos Updated January 2025!brbrSunnyside Escape is a newly built luxury home situated on the famous white sand gulf beaches of Anna Maria Island. The property is filled with top-of-the-line appliances and finishes throughout the home. Take in the view while lounging in the main living room, cooking, or enjoying a meal in the dining room. Large floor-to-ceiling windows allow spectacular views throughout the home. brbrThe large back deck has a space for everyone. Whether you are looking to soak in the sun in the gorgeous infinity pool, cookout your favorite meal in the outdoor kitchen, or lounge in the shade, Sunnyside Escape will provide! Take a quick stroll down to the water's edge with exclusive access to the gulf beaches. After a long day in the sun, the media room is the perfect refuge to watch a movie on the oversized sectional. Missing your Peloton rides while you are on vacation We have you covered with a Peloton bike in the upstairs gym. All you need to bring is your shoes and access to your account! brbrFloor 2 (main living level): brBedroom 1: King with TV and ensuite bathroom with walk-in showerbrMedia Room with large sectional with extra-large TVbrHalf bath in hallbrLaundry room with second half bath and direct access to pool patiobr(Please note that the fireplace in the living room and on balcony have been disabled and are not available for guest use.)brbrFloor 3:brBedroom 2: King master with TV, ensuite bathroom with walk-in shower, and Gulf ViewsbrBedroom 3: Queen Bed with ensuite bathroom with walk-in shower brBedroom 4: Queen Bed with ensuite bathroom with walk-in shower brExercise room with Peloton. brbrNOTE: For security and insurance purposes, there are exterior-only video cameras on the premises.brbr**PETS: Please note this property is NOT pet friendly. **brbrPARKING: 4 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. *Note that the garage is owner-use only and is not available for parking.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.

Bed

Bath

Sleeps

$801.62

/ Nightly

Private Vacation Home

Sandy Beach Retreat - 3 bedroom on the beach with amazing views and private pool

Anna Maria, Florida, United States

Welcome to Sandy Beach Retreat! You will fall in love with the beautiful beaches of Anna Maria Island as your backyard in this luxury vacation home! Spend your days lounging by the private heated pool or simply cross over to dip your toes in the Gulf waters. A one-of-a-kind, luxurious home located along the Gulf waters of Anna Maria! This multilevel 3-bedroom, 2.5 bathrooms home has all the best amenities featuring panoramic views, a private pool and an elevator to make bringing in your gear or groceries a breeze. Create your perfect beach getaway with family and friends as the home can comfortably sleep 6 guests! Literally just a couple steps from the sugary white sandy beach, close to incredible restaurants and shopping where you can find unique take-home treasures. Lazy beach days ahead!! Quiet spaces, large gathering spaces- this place literally has it all! When your day is done on the beach, then take a dip in the refreshing pool. Fire up the grill and take in the glowing sunsets nightly, straight from the comforts of your own beach house! In the evening, have your camera and cocktails ready! Sandy Beach Retreat will give your VIP sunset views from the privacy of your own home with open air decks. Great location and steps from the sand. Don’t feel like driving Then take a ride on the free Island trolley to other popular areas of Anna Maria Island where you can discover all the natural beauty this area has to offer. Grab your beach bags and escape from it all here at Sandy Beach Retreat! Home Layout: Bedroom #1: King Bedroom #2: King Bedroom #3:Twin

Bed

Bath

Sleeps

$902.09

/ Nightly

Private Vacation Home

Luxury North End Escape | 3 king beds + pool/spa

Anna Maria, Florida, United States

⭐️Super host Property + Verified for Cleanliness + Communication⭐br 228 Gladiolus Street - `Castaway Cove`br Castaway Cove | North End AMI | Pool + Spa + Walk to EverythingbrbrStay in the heart of the north end of Anna Maria Island at Castaway Cove, just steps from top restaurants, boutiques, Bay beaches, Gulf beaches, and the famous Anna Maria City Pier.brbr✨ Highlights:brbr• Private pool + hot tubbr• 3 King bedroomsbr• 2 full bathroomsbr• Sleeper sofa for extra guestsbr• Prime walkable locationbrbr Sleeping Setup:brbr• Primary: King bed, TV, ensuite with walk-in showerbr• Bedroom 2: King bed, TVbr• Bedroom 3: King bed, TVbr• Living Room: Sleeper sofabrbrEnjoy mornings at the beach, afternoons by the pool, and evenings dining just steps away — no car needed!brbrGood to Know:br• Entry code sent day of arrival after inspectionbr• Welcome book with WiFi + local tips providedbr• Rental agreement required prior to check-inbrbrCastaway Cove is the perfect island retreat for couples, families, or friends looking for location, comfort, and coastal charm all in one.brbrPlease note a starter set of supplies are left for your arrival. Anything beyond what is left renters are responsible for providing. Starter set includes. 2 rolls of toilet paper per bathroom, small hand soap, 1 roll of paper towels, 2 garbage bags, small dish soap and 2 pods for dishwasher.brbrPools are heated October - April at no additional costs. Full disclosure if temperate drop below 60 heaters do not work at full capacity fighting the ambient temp. Below 60 the heaters do not come on until temperatures risebrPlease Remember: You are vacationing in a residential area. Please be a good neighbor by keeping the noise to a respectful level. Noise ordinance is in effect 10pm to 7am. Excessive and unreasonable noise can result in disciplinary actions including fines and/or termination of your rental agreement without refund.brQuiet hours between 10pm - 6ambrNo partiesbrNo smoking

3

Bed

2

Bath

8

Sleeps

$812.8

/ Nightly

Private Vacation Home

North end AMI, 5* luxury home in one of the prettiest towns on gulf coast!

Anna Maria, Florida, United States

Welcome to Castaway Cove, this beautiful residence is a Bean Point gem, a stunning 4 bedroom property and 2.5 bathroom on the exclusive Northern end of Anna Maria Island! Hide away from the world, relax and soak up the sun in the private backyard with heated pool and lush tropical landscaping.brbrWalk to Pine Ave & City Pier from this designer 4BR/4.5BA home on Anna Maria’s coveted north end. Enjoy a private heated pool & spa, three suite bedrooms, a kids’ bunk room, and the convenience of an elevator — just a 5-minute stroll to the sugar-sand beach. brbrThe downstairs game room provides an excellent 8ft Pool Table and Air Hockey table, perfect for adults and kids, or enjoy either of the 2 Smart HD TV's (internet only). Want to work on your beach body during your stay Make use of the Bow-flex weights & treadmill in the Castaway Cove gym or stretch out your back on the inversion table! Have a refreshing outdoor hot or cold outdoor shower after the workout.brbrWe have 2 Adult Bikes, 2 Kids Bikes + one small Bike, all for you to use around the island at your leisure.brbrGet the best of both worlds in a gorgeous home with fantastic amenities and a great location with the pristine white sandy beaches of Bean Point just a short 2 minute walk away! Three houses to the beach. Other fantastic local spots to visit are the renowned Rod and Reel Pier and Restaurant located just a brief 4 minute walk away, or the beautiful, newly renovated Anna Maria Pier and the popular Pine Avenue showcasing local boutiques and restaurants and so much more!brbrThe sleeping arrangements include a King-sized bed in the Master bedroom, 2 Queen sized beds on the upper floor and a set of bunk beds-comfortably accommodating a group of 8.brbrEnjoy the fully equipped kitchen, with new appliances in 2023, ideal for making a home cooked meal with the fresh catch of the day or simply indulge in the local cuisine, there are many fantastic restaurants or home delivery to choose from! Our Bull Outdoor Kitchen is down by the pool to make the best BBQ in town, recently added our new pool bar with refrigerator to keep all those drinks ice cold!brbrFor your convenience, Wi-Fi internet, a stereo, DVD player and a TV in each bedroom is provided-although you will probably spend most of your time pool-side or catching the sun on the beach-the choice is up to you, you are on vacation after all!brbr**Please keep in mind if the elevator becomes inoperable due to any reason, the stairs will be the only form of transportation to and from your unit**brbrBaby care facilities include a high chair, a stair gate, 2 pack 'n' plays and a sun tent for the beach. There is also a large trunk of toys by the pool.

Bed

Bath

Sleeps

$729.93

/ Nightly

Private Vacation Home

Hop, Skip and a Beach - 4Bed Pool Home in Anna Maria City - By Island Real Estat

Anna Maria, Florida, United States

Oh so close to the beach all it takes is a Hop, Skip and a Jump to get to the Beach! This newer 4 bedroom private pool home is west of Gulf Drive in beautiful Anna Maria City. This home has everything you and your family will need, and is less than 2 minutes to the flour soft sand beaches of the Gulf of Mexico. Hop, Skip and a Beach is an elevated home that boasts a private heated pool with spa(hot tub) and many other covered areas poolside ideal for lounging after a busy day of exploring Anna Maria Island. Enjoy an outdoor meal under the covered lanai or the island tiki overlooking the spacious pool. There is also a brand new game room with bar, large TV, electronic dart board, and vintage fridge! Also take in a game of corn hole with custom boards offered by the owner.brbrThere are so many outdoor decks you will need to extend your stay in order to enjoy them all, and get yourself enough of the fresh sea air everyone talks about. The great room area is open to the fully stocked gourmet kitchen, living area and dining area. Just at the top of the stairs is a washer and dryer on the third floor for guest convenience. Three of the four bedrooms are located upstairs on the third floor including the Master suite. This private West of Gulf Drive home comfortably accommodates a group of 8 with a King sized bed in the master bedroom, a second master with King bed, a Queen bed in the fourth guest bedroom off the living area and a full over queen bunkbed in the third bedroom perfect for kids or adults.brbrHop, Skip and a Beach is located on the North end of Anna Maria Island in Anna Maria City. The elevated home is just a short trolley ride, bike ride or walk away from some of the great local shops and restaurants. Walk the beach for 15 minutes to the famed Sandbar restaurant for a beachside cocktail.brbrPlease note: this property books Saturday to Saturday. We may sometimes gladly accept non Saturday to Saturday stays from middle of August to middle of December or for short stays. Please ask a reservation specialist for more details.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.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.brbrbrVR17-000012brbrMax Vehicles Allowed:4 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.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.

Bed

Bath

Sleeps

$489.87

/ Nightly

Private Vacation Home

Dock of the Bay by Duncan Real Estate

Anna Maria, Florida, United States

Welcome to Dock of the Bay!br br Located on the North end of Anna Maria, Dock of the Bay is a newly remodeled two- bedroom, three-bathroom vacation home directly on a canal with a private pool. This property has boat access to the intercoastal passing 2 low clearance bridges. br br Dock of the Bay is a direct walk to Bean Point which is one of the most picturesque parts of Anna Maria Island.br br br HIGHLIGHTSbr br 2228 sq. ft. br Private Pool 35x20'br Boat dock br Canal accessbr Screened lanai br br Dog friendly up to 25 lbs.br br BEDROOMSbr br Sleeps 4br Primary Bedroom: King Ensuitebr Second Bedroom: Queen and bunk bedsbr br BATHROOMSbr br Primary Bathroom: Walk-in Showerbr Second Bathroom: Walk-in Showerbr Third Bathroom: Walk-in Shower br br EXTERIORbr br Relax on the large-screened lanai after a day at the beach and look out for mullets jumping in the canal. Take a dip in the lagoon shaped pool with shallow wading area. Dock of the Bay is located on quiet Gladiolus St and just a short walk away from the Bay side and Pine Avenue shopping area. Here you can try out the delicious local cuisines, browse through shops and much more! If you are looking to unwind, Dock of the Bay is your perfect location! Come experience for yourself all the best that Anna Maria Island has to offer!br br There are three parking spaces designated for this property in the driveway and garage.br br The weekly pool heat 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. 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 pools for maintenance purposes. No refund or rent adjustment except for pool heat fees will be made for circumstances beyond our control, malfunctions, or loss of use of equipment or amenities.br br br This property welcomes any day arrival for the months mid-August to January except holiday weeks. Please contact us for approval.br Amenities Include:br - Bedroom 1 Kingbr - Bedroom 2 Queen and bunk bedsbr - Bathroom 1 Walk-in Showerbr - Bathroom 2 Walk-in Showerbr - Bathroom 3 Walk-in Showerbr - Water View Ybr - Canal Viewbr - Canal Accessbr - Beach Access 0.3 milesbr - Ground Level Ybr - Central A Cbr - Cental Heatbr - Sqft under a c 2228 sqftbr - Parking Spotsbr - Garagebr - Dogs up to 25 lbs Ybr - Self Check Inbr - Keyless Entrybr - Bath Towelsbr - Beach Towelsbr - Quality Linensbr - Hair Dryerbr - Hangersbr - Refrigeratorbr - Ice Makerbr - Stovebr - Cookwarebr - Toasterbr - Blenderbr - Drip Coffee makerbr - Dishwasherbr - Microwavebr - Garbage disposalbr - Breakfast Barbr - High Speed WIFIbr - TV 3br - TV Streaming Onlybr - Washerbr - Dryerbr - Ironbr - Ironing Boardbr - Cleaning Kitbr - First Aid Kitbr - Fire Extinguisherbr - Smoke Alarmbr - Carbon Monoxide Alarmbr - Private Pool Ybr - Pool Dimensions 35x20'br - Spa Ybr - Pool Alarmsbr - Sun Loungersbr - Screened Lanaibr - Outdoor Diningbr - Boat Dockbr - Fishing Dockbr - Propane Grillbr - Beach Amenitiesbr - Board Gamesbr - Exterior Outletbr - Duncan Emerald Club

Bed

Bath

Sleeps

$292.67

/ Nightly

Apartment

2b/1.5ba duplex unit short walk to gulf beach in quiet Anna Maria neighborhood.

Anna Maria, Florida, United States

216 Spring Avenue, is a 2b/1.5 duplex apartment located approximately 2 blocks to gulf beach where you can enjoy nice walks along the shore and view beautiful sunsets. Centrally located to several restaurants, shops and trolley stop to enjoy rides on the island free trolley. Fully furnished apartment with a well-equipped kitchen, and small screened porch off living room. All towels and linens included. Amenities include Washer/Dryer, Dishwasher, Wireless Internet, *Streaming TV & Antenna (*Tenant must be subscribed to their own streaming apps for TV use). Solar powered security camera installed in front and back of unit. *Starter set of toilet paper, paper towel & hand soap supplied. *Note beach chairs and beach toys NOT included.

Bed

Bath

Sleeps

$766.89

/ Nightly

Private Vacation Home

Blue Mermaid Beach Bungalow

Anna Maria, Florida, United States

Highlightsbr- 2 minute walk to the Beach of Anna Maria Islandbr- 5 minute walk to Pine Ave.br• Private Poolbr• Outdoor Showerbr• Beach gear (chairs, umbrella, towel, kid's toys)brbrBlue Mermaid by Reel Coastal Propertiesbr111 Sycamore AvebrAnna Maria, FL 34216brbrWelcome to Blue Mermaid, where you are just one house away from the beach! Take a quick walk to the warm white sands and relax to the sound of ocean waves. The backyard features a private pool surrounded by lush landscaping, lounge chairs, and a screened-in patio where you can retreat for deep relaxation and even watch your favorite movies on tv. This vacation home is situated two blocks from Anna Maria Island’s famous Pine Avenue, so there will be no shortage of flavorsome local treats or boutiques.brbrThe Blue Mermaid is an enchanting three-bedroom, a two-bathroom beach vacation home. The living area’s coastal décor provides a welcoming atmosphere where conversations and relaxation are encouraged. Open the sliding glass doors to the patio where your guests enjoy early morning coffee or late-night drinks while taking in the ocean view. The fully equipped kitchen has festive Caribbean hues, broad kitchen countertops that make meal preparation a breeze, and plenty of cabinet space to store your goodies and ingredients for an excellent best island meal.brbrThe primary bedroom’s vibrant tropical colors are sure to brighten up your vacation, and the ensuite bathroom features a shower/tub combo. The second bedroom has beautiful island décor and the opportunity to open the shuttered windows to gaze upon the lush landscaping and to bring in the Anna Maria sun. The third bedroom is perfect for younger guests and has a tv for late-night show watching. The second and third bedrooms share a hallway bathroom that has a shower/tub combo.brAfter a beautiful day at the beach, retreat to your backyard, where you can lounge by the pool and take a shower at the outdoor shower located on the backside of the house. Cook up some of your family favorites on the charcoal BBQ grill to enjoy at the outdoor dining table. Explore Anna Maria Island on your own or check out the local tour guides to show you some local treasures on the land and at sea! Blue Mermaid is so close to the delicious restaurants and locally owned boutiques that it is sure to have something for everyone in your group.brbrRoom Detailsbr- Primary Bedroom, 2nd floor: King bed, tv, and ensuite bathroombr- Second Bedroom, 2nd floor: King bed and tv.br- Third Bedroom, 2nd floor: Twin beds and tv.brbrThere are no pets allowed in this home.brbr*Please note: 3 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.brbrPlease Remember:brYou 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*Exceeding the noise ordinance could result in disciplinary actions including fines and/or termination of your rental agreement without refund.

Bed

Bath

Sleeps

$875.43

/ Nightly

Private Vacation Home

Canalfront Island Gem with Private Heated Pool, Dock, Ping-Pong, & Putting Green

Anna Maria, Florida, United States

Mermaid ManorbrbrOur calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired dates and click 'Book Now!'brbrThe island lifestyle will be hard to leave once you indulge in a stay at this gorgeous retreat in the heart of Anna Maria. Boasting a bright interior, driftwood-inspired floors, and shiplap walls, this will be just the place to spoil even the most design-oriented of guests. Start each morning with a warm cup of coffee on the furnished balcony as you look out to the canal system and plan a full day of fun. When days heat up, everyone can head out to the private pool (can also be heated upon request!) and lounge in bliss while the kids play in the refreshing water. Whipping up poolside snacks and gourmet meals will be easy in the fully equipped kitchen and everyone will love eating al fresco on the covered deck! After watching the sunset from your favorite spot, head inside and you will have the option to gather for a movie night on one of the flatscreen TVs or let your competitive side out with a ping-pong tournament! Additional entertainment can be achieved thanks to the professional-grade 4 hole putting green - the putters and balls will be provided to you, so there's no need to worry!brbrHeading to bed each night will be a treat in itself, as each bedroom is immaculately furnished and decorated. Starting from the entrance of the home, the first three bedrooms can be found by following the hall directly to the right at the top of the stairs. On the right side of the hall is a bedroom with a twin/double bunk bed. The next bedroom offers a queen bed. Plus, a full bathroom is located at the need of the hall. On the left is a master suite with a king bed and a beautiful en suite bathroom. Make your way to the other end of the home and you will find the last bedroom located off of the living area that is complete with a queen bed and easy access to another full bathroom across the hall. brbrThere will be no lack of excitement on this vacation, as Anna Maria is packed with fun for the whole family to enjoy. With access to Bimini Bay via the unique canal system, taking your boat out for a day on the emerald water of Tampa Bay will be a breeze. Sugar-white sand can be found just blocks away, or you can make your way to Bean Point Beach for room to spread out and watch the waves just over a mile from your front door. When the group works up an appetite, amazing restaurants like The Waterfront Restaurant, Rod and Reel Pier, and The Sandbar Restaurant will be just the ticket for a plate of fresh seafood. brbrTHINGS TO KNOWbrPool heat is included and maintained at 80°F. Additional pool heat to 85°F is available upon request for $32 per day plus tax. A 48 hour notice is required. Heat may not be available if temperatures drop below 65 degrees. We will not be accepting payments for pool heat for the months of May through OctoberbrThe golf cart is not for guest use.brbrParking notes: There is free parking available for 2 vehicles.brbrDock details: brbrbrbrDamage waiver: The total cost of your reservation for this Property includes a nightly damage waiver fee, plus tax if applicable (the “Damage Waiver”). (A discount may be applied for stays of 28 nights or longer, if permitted.) The Damage Waiver covers you for up to $3,000 of accidental damage to the Property or its contents (such as furniture, fixtures, and appliances) as long as you report the incident to the host prior to checking out. The Damage Waiver fee eliminates the need for a traditional security deposit.brMore information can be downloaded from the Rental Agreement on the checkout page.brbrDue to local laws or HOA requirements, guests must be at least 21 years of age to book. Guests under 21 must be accompanied by a parent or legal guardian for the duration of the reservation.

Bed

Bath

Sleeps

$307.29

/ Nightly

Condo

Beautiful Villa, Perfect Small Getaway. Close to beach, beach gear provided!

Anna Maria, Florida, United States

Seeking a private piece of Anna Maria Island charm This Anna Maria rental is ideal for a small family, a romantic escape, or a long overdue, quiet catch-up with close friends. Palm Court is an updated villa which sleeps 4, making it perfect for smaller groups. But don’t let the small size fool you, Palm Court Villas has everything you need for the ultimate vacation.brbrPalm Court is ideally situated in the heart of Anna Maria Village. Take a short walk to experience great shops, diverse restaurants, fishing piers and the Community Center. Beautiful white sand beaches are just one short block away and feature a wonderful row of Australian pine trees for shade and cool relaxing. When you’re ready to explore, jump on the free Island trolley that stops at the corner of Magnolia Ave and runs the entire length of Anna Maria Island.brbrThe owners have thought of all conveniences. You will find a modern, fully equipped kitchen, ample linens including beach towels, washer/dryer, and comfortable furnishings. There is a beach gear shed with beach cart, umbrella, chairs, and sand toys. The open tropical courtyard is a wonderful place to enjoy a late afternoon margarita or a relaxed dinner prepared on the charcoal grill.brbrSo, pack your flip flops, and get ready to enjoy charming Palm Court. And if you have a larger group, Villa A can be rented along with Villa B to allow a party of 8 to enjoy all this lovely rental has to offer.brbrbrFlexible check in days for most of the year--with the exception of holidays. Friday arrivals and departures during Peak Season. brbrIf you love this rental but are not getting a quote with the dates you've selected contact us so we can check the availability for you!brbrPlease note that pets are not allowed in this rental.brbr210 B MAGNOLIA ALSO AVAILABLE --RENT BOTH VILLAS TO ACCOMMODATE UP TO 8 GUESTS.brbrVacation rental professionally managed by Fran Maxon Real Estate, Inc

Bed

Bath

Sleeps

$821.14

/ Nightly

Cottage

Luxury Beach Cottage for Families on the North Shore of Anna Maria Island

Anna Maria, Florida, United States

Beach chic meets casual elegance in this brand new ground level cottage only steps away from the best beach on Anna Maria Island. The Beach Cottage is across the street from the soft white sand beach and turquoise waters. At dusk watch the most spectacular sunset over the water on the best spot on the Island, Bean Point. Pine Street is just a few blocks away where you can bike to your favorite local eateries and shops. brbrThe first room you enter at The Beach Cottage is a large screened in porch with plenty of seating for relaxing, reading a book, drinking your morning coffee, or your glass of wine after dinner. From the screened in porch you enter the large family room complete with comfy couches for an entertaining family game or movie night. The Beach Cottage is equipped with a large gourmet kitchen with state of the art appliances. Right outside of the kitchen is a gas Weber grill to maybe enjoy your fresh catch of the day next to your private heated pool. There are two master bedrooms, both with king size beds. One of the master bedrooms has its own private bathroom while the other has a pocket door to the shared bathroom. The kids room, which sleeps four, has custom built bunk beds complete with reading lights and book shelves. Each of the bedrooms have smart TVs.brbr**We also rent out the property next door and can rent out both for large parties, if the cottage is booked take a look at this property! brhttps://www.homeaway.com/vacation-rental/p3504493vb uni_id=4077639

Bed

Bath

Sleeps

$769.67

/ Nightly

Private Vacation Home

Beach Bay Serenity: Pine Ave canal front pool home

Anna Maria, Florida, United States

Welcome to Beach Bay Serenity!brbrThis gorgeous 4 bedroom 3.5 bath waterfront home located on Pine Avenue is the perfect place to enjoy your next vacation!brbrBeach Bay Serenity is an immaculate home with updated features throughout. This home offers open living space, canal views, spacious kitchen with built in dining area, solid wood cabinets, granite countertops, elevator, large master suite with separate tub and shower, private deck off the master, walk-in closets, 2nd master suite, Guest bedroom, Bunk bedroom, and garage. Beach Bay Serenity offers direct access to Tampa Bay and The Gulf of Mexico. Relax and entertain outdoors by the heated pool! Conveniently located on Pine Avenue you have many restaurants and boutiques right at your door step! Bring your boat and dock directly in your backyard or enjoy fishing off the dock. Leave the car at home with the free Anna Maria Trolley passing right by your front door, travelling throughout the island very convenient!brbr**Please note that boat lift is not available for guest use.brbr*Please note: 4 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.

Bed

Bath

Sleeps

$605.04

/ Nightly

Private Vacation Home

Point's Hideaway - Luxury Retreat w/ Private Pool & Deck, Stunning Bay Views

Anna Maria, Florida, United States

Welcome to Point's Hideaway!brOn Anna Maria Island (Anna Maria, FL)brbrPlease note: The home is next to a construction site. There is no set construction schedule, and activity may occur during your stay.brbrThe SpacebrEvery corner of Point's Hideaway reflects a gentle harmony of light, air, and comfort. With open living spaces that flow into outdoor terraces and a rooftop deck that opens to the Gulf's evening glow, the home offers a seamless connection between indoors and out. Whether you're sipping coffee on the screened porch or watching the sun fade into the horizon from above, this home was designed for dreaming.brbrPerfect for: couples seeking tranquility, families who love water views, and travelers drawn to the softer side of island life.brbrHighlightsbr- Steps from Bean Point Beach and near Pine Avenue's shops and restaurantsbr- Panoramic rooftop deck with breathtaking views of the bay and sunsetbr- Private heated pool with lounge seating, dining table, and grillbr- Screened-in porch with outdoor dining and relaxation areasbr- Game room and bar area with wet bar, beverage cooler, and TVbr- Chef-inspired kitchen with gas range, stainless appliances, and wine coolerbr- Pet friendly with prior approvalbrbrInteriorbrInside, natural light filters through high ceilings and open spaces, reflecting hues of sea glass and driftwood. The living area invites connection with comfortable seating, a smart TV, and sliding doors that lead to the screened porch for easy indoor-outdoor living.brbrThe kitchen features sleek finishes and thoughtful details—gas range, oven, refrigerator with ice and water dispenser, microwave, dishwasher, wine cooler, and all the essentials for preparing a shared meal.brbrEach bedroom offers a retreat of its own, designed with care and a touch of coastal calm.br- Master Suite: King bed, walk-in closet, en-suite bath with walk-in shower and double vanity, and direct access to the rooftop deck.br- Second King Suite: En-suite bathroom with a jetted tub/shower combination.br- Third King Bedroom: Adjacent to a full bathroom with a walk-in shower.br- Sleeper Sofa: Comfortably accommodates two additional guests.brbrLayout Overviewbr- Ground Level: Game room with wet bar, beverage cooler, and TV; access to the pool and outdoor areas.br- Second Floor: Open-concept kitchen, dining, and living areas with vaulted ceilings and screened-in porch; King bedroom and full bath with walk-in shower.br- Third Floor: Two King bedrooms, each with en-suite baths; rooftop deck access from the primary suite.brbrOutdoor LivingbrPoint's Hideaway was made for open-air living. The private heated pool offers a sunny retreat surrounded by loungers, a dining table, and a gas grill. The screened-in porch becomes a peaceful spot for morning coffee or evening conversations, with soft breezes drifting in from the bay.brbrClimb to the rooftop deck to experience panoramic views that shift from bright blues to fiery sunset tones. This elevated space is perfect for quiet reflection, sunset toasts, or simply listening to the stillness that comes when the island slows down.brbrKitchen & DiningbrThe heart of the home is a chef-inspired kitchen designed for both function and togetherness.br- Gas range and ovenbr- Dishwasher and microwavebr- Refrigerator with ice and water dispenserbr- Wine cooler and coffeemakerbr- Blender, toaster, and kitchenwarebr- Gather around the indoor dining table or move outdoors to dine under the screened porch while the evening breeze carries the sound of the Gulf.brbrAdditional Amenitiesbr- Air conditioning and heatbr- Cable television and Wi-Fibr- Linens, towels, and hair dryersbr- Washer and dryerbr- Iron and ironing boardbr- Beach gear rental credit included (chairs, cart, umbrella, bikes, etc.)br- Some beach gear may be available onsite, but it is not guaranteed.brbrParkingbrTwo-car garage plus driveway parking for up to two additional vehicles.brbrAt Point's Hideaway, write your vacation story where sunrises meet bay breezes and every evening ends in a sunset worth remembering.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: VRC24-000081brMax Occupancy: 8 Guests | Max Vehicles: 3brInformation deemed reliable but not guaranteed; subject to change or withdrawal without notice.

Bed

Bath

Sleeps

$568.02

/ Nightly

Private Vacation Home

Vintage Cottage: Pool and Walk to Beach, Pine Ave Shops

Anna Maria, Florida, United States

Buttonwood Cottage by AMI Locals brbrWelcome to Buttonwood Cottage, a recently restored three bedroom, two bathrooms home full of Florida charm. Perfectly located on iconic Pine Avenue in Anna Maria and 10-minute walk to the Gulf. With a private heated pool, a pet-friendly policy, and easy access to island boutiques, restaurants, and attractions, this cottage is a delightful retreat for families and friends looking to experience Anna Maria Island’s vibrant coastal lifestyle. brbrHighlights br-10-minute walk to the beach and bay br-3 Bedrooms / 2 Bathrooms br-King bed, Queen bed, 3 Twin beds br-Private heated pool br-Pet friendly with host approval br-Outdoor shower and covered patio br-Dedicated workspace and chalk wall br-Washer and dryer br-Near shops, cafes, and restaurants on Pine Avenue br- 4 Parking spots. brbrThe tropical backyard oasis features a sparkling heated pool, perfect for a refreshing swims after a day at the beach! A covered patio with seating and a BBQ grill sets the stage for casual outdoor dining, while the outdoor shower makes rinsing off sandy toes easy and convenient. brbrStep inside to discover a bright, open concept layout blending nautical accents with modern comfort. The living room features a plush sofa, leather recliners, and TV for streaming your favorite shows. The gourmet kitchen includes stainless steel appliances, a large island, and all the cookware essentials for preparing delicious meals. The dining area boasts a stunning solid wood table with seating for the whole group. A corner desk provides a convenient workspace for remote work or study. brbrThe primary bedroom is a serene retreat with tall wooden beams, a king bed, luxury linens, ample storage, and a flat-screen TV. The second bedroom offers a queen bed and a twin bed, decorated with cheerful colors and warm flooring. The third bedroom is perfect for kids or extra guests with two twin trundle beds, patio access, and a washer and dryer for added convenience. The two bathrooms include a tub-and-shower combination and a walk-in shower, ensuring plenty of comfort for everyone. brbrRoom Details br-Primary Bedroom: King bed br-Second Bedroom: Queen bed and Twin bed br-Third Bedroom: Two Twin trundle beds brbrButtonwood Cottage includes family-friendly features like a chalkboard wall for creative fun, Wi-Fi, washer and dryer, and parking. Guests can also take advantage of the Anna Maria Island trolley, just steps away, for exploring the island’s seven miles of beaches, piers, and preserves. brbrFrom its prime location on Pine Avenue, you’ll enjoy walking to local cafes, boutiques, art galleries, and even the famous Doughnut Experiment for your morning coffee and pastry. With the Gulf just three blocks away, you’re perfectly positioned to enjoy the best of Anna Maria Island. brBook your stay at Buttonwood Cottage today and immerse yourself in the charm of Florida living with all the modern comforts you need for a perfect Coast vacation! brbr- 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. 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. brbrThis home is managed by AMI Locals, an Anna Maria Island property management company. 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 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.

Bed

Bath

Sleeps

$1068.9

/ Nightly

Private Vacation Home

Luxury Island Retreat: Pool, Spa and Walk to Beach

Anna Maria, Florida, United States

Endless Summer by Anna Maria Island Accommodations brVR19-000059 brbrWelcome to Endless Summer, a stunning five-bedroom, six-and-a-half-bath vacation home ideally situated in the heart of Anna Maria. Just one street over from the vibrant Pine Avenue, you’ll be moments from favorite island spots like The Donut Experiment, Ginny’s & Jane E’s, and Poppo’s Taqueria, plus unique boutiques and ice cream shops. With the Gulf beaches only a short stroll away, this elegant retreat combines luxury interiors with a private backyard oasis. Perfect for families and friends looking to relax, explore, and make unforgettable memories on Anna Maria Island. brbrHighlights br-7-minute walk to Anna Maria Beach br-5 Bedrooms / 6.5 Bathrooms br-4 King bedrooms, 1 Full-over-Full bunk room br-Private heated pool and spa br-BBQ grill br-Covered patio with plenty of seating br-Second-floor lounge with TV br-Washer and dryer br-Dog friendly br-4 parking spaces brbrStep outside and experience your own private oasis. The heated pool and spa invite you to soak up the Florida sunshine or relax in the shade of the covered patio. An outdoor kitchen with built-in BBQ grill makes dining outdoors a breeze, while comfortable outdoor seating provides the perfect spot to gather with family and friends. Whether you’re swimming, cooking, or simply enjoying the tropical landscaping, the backyard at Endless Summer is designed for both fun and relaxation. brbrInside, it boasts an open concept main living area with plush seating, a TV, and large windows that fill the space with natural light. The gourmet kitchen is equipped with stainless steel appliances, ample counter space, and a dining table with seating for the whole group. A convenient half bath and laundry area are also located on the main floor. Upstairs, a cozy family lounge with a TV provides an additional gathering space, ideal for kids or group movie nights. brbrUpstairs, unwind in a cozy second-floor lounge, a perfect spot for game nights. Two additional bedrooms, both with ensuite bathrooms, provide privacy and comfort. A full hallway bathroom with a shower/tub combo offers added convenience. Each bedroom features crisp linens, TVs, and thoughtful decor to make every guest feel at home. brbrRoom Details br-Primary Bedroom (2nd Floor): King bed + ensuite bathroom with walk-in shower br-Second Bedroom (2nd Floor): King bed + ensuite bathroom with walk-in shower br-Third Bedroom (2nd Floor): Full over Full Bunk beds br-Fourth Bedroom (3rd Floor): King bed + ensuite bathroom with walk-in shower br-Fifth Bedroom (3rd Floor): King bed + ensuite bathroom with walk-in shower brbrLocated just a 7-minute walk to the beach and only steps from Pine Ave, Endless Summer is perfect for families or groups looking to experience the best of Anna Maria Island. Ride bikes, hop on the AMI trolley, or simply explore the island by foot. brbrDon’t wait. Book your getaway to Endless Summer and start living your dream island vacation today! br br- br*Please note: 4 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. 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. brbrThis home is managed by AMI Locals, an Anna Maria Island property management company. 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 Remember: brYou 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.

Bed

Bath

Sleeps

$1034.55

/ Nightly

Private Vacation Home

H2O Bungalow by Beach Boutique Rentals

Anna Maria, Florida, United States

H2O Bungalow is a 3 bed, 3 bath stunning vacation home that is unique and unlike any others. brbr*Features include* brbr* Private lazy river pool with hot tub! br* 3 bedrooms, 3 full bathrooms br* 2 master king suites br* Fun bunk bedroom for the family br* Gourmet kitchen and spacious dining room br* Washer and dryer br* Massive outdoor space with loungers, tables + charcoal grill br* Patio dining table for 6 br* Less than 2 blocks to the beach br* Dog Friendly! brbrThere is nothing else on the island quite like the Polynesian inspired backyard at H2O Bungalow! You will have your own private retreat complete with a spectacular lazy river, waterfalls, a stone bridge and Easter Island statues. The amazing pool also features fountains and a large hot tub for relaxing. While the family enjoys the pool, cookout on the charcoal grill and and then dine outside amidst the tropical landscaping. brbrWe won't blame you if you never want to leave this backyard, but when you do the beautiful white sand Gulf beach is less than a short two blocks away. Less than a 10 minutes stroll down Gulf Drive will lead you to several shops and restaurants. You can also hop on the Island Trolley right near the house and let it carry you where you want to go, from Pine Avenue to Coquina Beach. brbrInside H2O Bungalow you'll find all the comforts of home with finishing touches that give it an upscale feel. The large flat-screen TV in the living room offers cable channels as well as your favorite streaming services. The kitchen is open and spacious, featuring a huge island with plenty of seating. Order in or cook a fantastic meal on the glass cooktop and double oven. Whichever you choose, the 8-top dining table offers all the space you need for a sit-down meal. brbrWhen you retreat to bed for the evening, choose from one of three roomy and inviting bedrooms. The master suite offers a king bed, TV and ensuite bath. The second bedroom also includes a king bed and can function as a second master suite with its own hall by closing the barn door closed to the living room. Kids will love the nautical-themed third bedroom with two twin bunk beds plus trundle which can sleep up to 5.brbrThis home is the whole package! Your dream Anna Maria Island vacation begins with H2O Bungalow. brbrPET POLICY: brbrWe are DOG FRIENDLY! A fee of $150 + tax is required in advance for each dog you are bringing. brbr2 pets maximum unless granted an exception. Weight limit of 75 lbs maximum per pet. brbrDue to property insurance policies and liability concerns NO dangerous breeds or aggressive animals are allowed. The following breeds (purebred or crossbred) are not permitted: brbrPit Bull, Akita, Rottweiler, German Shepherd, Siberian Husky, Malamute, Doberman Pinscher, Chows, Any Wolf-dog hybrid, Any other dog that has been known to have bitten anyonebrbrADDITIONAL INFORMATION brbrWe generally require a minimum stay during the high season. We are more flexible in the off season so please send us a message if your dates appear unavailable. We may be able to accommodate you! brbrHousekeeping will provide a starter supply of toilet paper, soap, and garbage bags but guests will likely need to replenish the supply during their stay. brbrOur cleaning fee includes a professional linen service. When you stay with us you can rest assured that you will have high quality linens such as those at a fine hotel. We also provide plenty of luxury bath and beach towels. brbrAnna Maria Island is a family community and the city imposes a strict noise ordinance. Please adhere to our good neighbor policy and observe the local quiet hours between 10 pm and 8 am. No loud music or use of the pool is allowed during these hours along with any other noise which may disturb the neighbors. brbrThis home provides off-street parking for up to 3 vehicles.brbrBooking Platform Note:brFor VRBO bookings, the reservation payment is processed by Beach Boutique Rentals and will appear as Beach Boutique Rentals on your credit card statement. VRBO also charges a separate service fee directly to the guest as a separate transaction.

Bed

Bath

Sleeps

$516.85

/ Nightly

Private Vacation Home

AMI Bay Breeze: Heated pool, outdoor bar, beautifully updated

Anna Maria, Florida, United States

Welcome to AMI Bay Breeze! This newly renovated, 3 bedroom 2 bathroom home is the perfect escape for your next vacation to Anna Maria Island! AMI Bay Breeze includes a king master with a walk-in shower ensuite bathroom, a king guest bedroom, 2 twins in the 2nd guest bedroom, and a large shared bathroom with a walk-in shower and the living room couch pulls out into a queen bed. The property provides a built-in laundry room with brand new washer and dryer as well as a fully stocked kitchen for cooking meals at home! If you didn't think the home could get any better, the outdoor area is a vacationers dream! The large pool with fully furnished patio is the perfect place to lounge in the sun or to dine al fresco. The outdoor bar provides a full size refrigerator, small sink for washing up, as well as plasticware to use by the pool. Enjoy the corn hole set or ping pong table for even more outdoor fun!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.

3

Bed

2

Bath

8

Sleeps

Vacation Rentals By Owner In Anna Maria, FL

$1565.8

$728.93

$522.66

$3445.6

$801.62

$902.09

$812.8

$729.93

$489.87

$292.67

$766.89

$875.43

$307.29

$821.14

$769.67

$605.04

$568.02

$1068.9

$1034.55

$516.85

Rent a place that suits your needs

Most popular vacation rentals in Anna Maria

$1989.44

$2381.19

$2367.68

$2337.14

$2162.54

$1896.38

$1761.71

$1888.73

$2397.49

$1926.55

Most Popular Cities in Florida