Vacation Rentals By Owner In Anna Maria, FL

Welcoming and gulf coast colorful, guests who enter Suite 4 often find an involuntary smile spread across their face as they enter the warm and inviting island feel of Suite 4. Every surface has been beautifully crafted from fine finishes, including marble, cast glass, shell stone, and porcelain to provide a luxurious, functional, and modern space that cannot be found anywhere else on the island. For your convenience, a fully stocked efficiency kitchen provides a convection cooking and microwave oven, large under-counter refrigerator, toaster and coffeemaker with ample storage for groceries and your belongings. Imagine the comfort of cool pressed 600 count linens, feather pillows, and airy 100% cotton bedding as you settle in after a day of island adventure, fun, and relaxation. Our rooms provide complimentary toiletries, beach towels, and an island guide so that your vacation and pampering can begin as soon as you walk through our door.

The Rod and Reel Resort-Suite 4

Anna Maria, Florida, United States

Bed

Bath

Sleeps

$1144.1

Willow Walk by Anna Maria Life Vacation Rentalsbr110 Willow Ave, Anna Maria, FL 34216brbrWhat You'll Love About This Home:brLocation! 3 Houses to the Beach!br4 Bedrooms / 3 Bathroomsbr3 King Beds / Set of Twin over King BunkbesbrPrivate Heated PoolbrOutdoor ShowerbrPool LoungersbrPatio Dining for 6 with UmbrellabrCovered Poolside Lounge Area with TV & FridgebrGas GrillbrFoosball & CornholebrProfessional Linen Service, Washer & DryerbrComplimentary WIFIbrBeach Towels, Beach Chairs & Beach WagonbrParking for 4 CarsbrbrDetails:brWith the sugar sand beach at the end of the street, Willow Walk is three houses from the Gulf of Mexico. Feel the island breezes and relax in our four-bedroom vacation home.brbrOur elevated home features the main living area, kitchen and dining room on the second level. The many windows provide an abundance of natural light to the living spaces. Your guests will enjoy a dining table that seats eight and kitchen counter seating for four.brbrTwo of the king bedrooms include an ensuite bath with the other guest rooms feature a king bed and a set of twin over king bunkbeds. Each bedroom has a TV and includes 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.brbrEscape to the lush and tropical backyard highlighted by the sparkling heated pool. Surrounded by pool loungers, an outdoor shower and a patio dining table for six, this is the place to spend an afternoon! The poolside lounge area has comfy sofas, a TV, fridge and foosball and cornhole games.brbrBedroom 1: King with TV and Ensuite Bath on Floor 2brBedroom 2: King with TV on Floor 2brBedroom 3: King with TV and Ensuite Bath on Floor 2brBedroom 4: Set of Twin over King Bunkbeds with TV on Floor 2brbrPlease note:brPets are not allowed in this home.brAmenities are subject to change.brbrWillow Walk is easy walking distance to many shops and restaurants, and less than a block 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.brbrVR16-000351brbrGolf 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.

Willow Walk: 3 Homes to Beach! West of Gulf Dr, Pool, Poolside Lounge Area by Anna Maria Life

Anna Maria, Florida, United States

Bed

3

Bath

8

Sleeps

$819.43

Anna Maria’s finest and most exclusive 2-bedroom accommodation awaits guests who reserve our largest and most luxurious Suite 6. Enter a set of double French doors into the main living space and master bedroom, or choose a second private entrance into this spacious 3-room apartment. Unparalleled design and finishes welcome guests to the comfort of the large living area featuring imported Italian marble floors and counters, leather seating, large screen TV, and a half bathroom. Guests are also provided the added amenities of on-site laundry facilities, full refrigerator, full oven, and dishwasher appliances in this well appointed and designed for comfort oasis. Imagine the comfort of cool pressed 600 count linens, feather pillows, and airy 100% cotton bedding as you settle in after a day of island adventure, fun, and relaxation. Our rooms provide complimentary toiletries, beach towels, and an island guide so that your vacation and pampering can begin as soon as you walk through our door.

The Rod and Reel Resort-Grand Suite 6

Anna Maria, Florida, United States

Bed

Bath

Sleeps

$745.11

Discover island paradise at North Shore located on the *premier corner* of North Shore & Palmetto in Anna Maria, only 2 blocks from the gorgeous, white sandy beaches of Anna Maria Island and a few steps from very popular Slim's Place restaurant and sports bar. This *ultimate beach house* has been fully renovated in 2025.br br Enjoy *single-story beach house living* with *seamless flow* between the house and private pool/spano steps to climb! br br Amenities include:br br Professionally designed, all new coastal modern furnishings br * Stunning saltwater pool* with sun shelf and large heated spabr Mature landscaping around lush private yardbr Private exterior shower cabanabr Large travertine patio with chaise lounge chairs, dining area and shade umbrellasbr 3 bedrooms, 1 bonus room (used as bedroom), 3 bathrooms:br 1 bedroom has king bed with private ensuite bathroom br 1 bedroom has king bed with adjacent full bathroombr 1 bedroom has queen bedbr 1 bonus room (converted climate controlled garage) furnished with 1 king bed, with small ensuite bathroom/laundry roombr Close proximity to Pine Ave. offering exquisite dining, shopping, bicycle and golf cart rentals, free island trolley and much more (All of the favorite shops and restaurants have reopened from the storms.)br New restaurant style, fully equipped kitchen offering stainless steel amenities and brand-new stainless-steel appliances br Fully screened lanai with 2nd dining areabr Gas barbecue br 1 beach cart, 4 beach chairs and 2 umbrellas providedbr 2 parking spaces in front of the house (garage is not accessible for parking)br New washer/dryerbr Free high-speed wireless internetbr TV, internet and phone service provided by Spectrumbr br Disclaimers:br br *Florida Law requires an audible alarm to be installed on doors and windows that open to a pool area. The purpose of these alarms is to alert an adult if a child walks out to a pool area unattended. These alarms typically have a bypass button that allows the door to be opened for 7 seconds before the alarm goes off. These alarms must not be removed or tampered with in any way. Any evidence of tampering or damage to pool alarms will be billed to the credit card on file for the reservation.* br br *Dogs 25lbs or less are welcome, A $ 250+ tax pet fee is required per pet, This is a separate fee paid directly to Salty Mermaid Real Estate after booking. Pets that are not disclosed to our office will result in additional cleaning charges to your reservation.br br *Check-in time is 4 pm on the day of your arrival, and check-out time is 10 am on the day of your departure. No early access or late departure is allowed unless special arrangements are made with our office, our cleaning and Inspection team need time to ensure the rental is clean and safe for your stay*br br *White Duvet covers and inserts, white bed linens, multi color beach towels, white bath towels, white wash clothes, white bathroom floor towels, black makeup towels, kitchen towels, premium pillows, vacuum sealed throw blankets*br br *A starter kit of paper towels, toilet paper, trash bags, laundry detergent, and coffee & tea. Full sized luxury hand soap, shampoo, conditioner, and body wash are provided at check-in. Also available if requested, while supplies last, is a toothbrush and sewing kit. Any additional items that you may need during your stay can be purchased at one of the local grocery stores.*br br *Please note, all guests occupying this property who are under the age of 25 must be accompanied by a parent or legal guardian*br br *Please note this is not a party or large gathering house. Noise complaints will result in eviction*br br *Reservations that are 30 nights or longer will require a mid-stay clean, one of our rental agents will provide more information at the time of booking*br br *No parking in the street or grass, please be careful of the neighbors' properties*br br *Pools are heated from approximately Thanksgiving to Easter only and are set no higher than 80 degrees. Spa temperatures default to the pool temperature when not in use and can reach 100 Degrees under normal weather circumstances. During colder weather, we cannot guarantee that the pool/spa can be maintained to that degree. No refunds, credits, or discounts will be offered if the pool/spa temperature cannot be maintained due to unusually cold weather*

North Shore Very Walkable to AMI fun & close to the Beach, Stunning Pool

Anna Maria, Florida, United States

Bed

Bath

Sleeps

$624.34

brThis rental is part of the Anna Maria Beach Cottages. More information on this charming property below!brbrFlirty Flamingo Cottage is your fun and funky ticket to a fabulous Anna Maria Island vacation experience! Cottage 112 of the charming Anna Maria Beach Cottages is a 3 bed/2 bath standalone vacation home with a bonus bedroom on Oak Avenue, just three houses from the beach.brbrThis cottage was recently redecorated with beachy chic décor for a bright and cheerful atmosphere throughout. For soaking up the sunshine and fresh Florida air, there’s a beautiful deck just off the dining room with a table for four under the vine covered trellis. Featuring a full kitchen, separate dining area, spacious living room, two full bathrooms, and a private charcoal grill, you’ll have everything you need for a fun-filled and comfortable stay. brbrEnjoy room for a group of up to 8 guests with 3 bedrooms and a bonus sleeping room. The master bedroom includes a king bed with a TV and private ensuite bathroom. The second bedroom has a queen bed, also with a TV. The third bedroom has a Queen bed. The bonus sleeping room has two twin beds offering even more options for alternate sleeping arrangements.brbrIn the master bathroom, there’s a spacious walk-in shower. And the guest bathroom includes a shower/tub combination, perfect for groups with small children. brbrYou’ll also have access to all the amenities the Anna Maria Beach Cottages has to offer, including a heated pool with a lounge area, assorted beach gear, bikes, picnic area with grills, onsite laundry and an on-site office for area information and support during your stay. Continue reading for more about this sweet and enchanting place!brbrPlease note that pets are not allowed in this rental.brbrbrABOUT ANNA MARIA BEACH COTTAGESbrbrBe whisked away to an Old Florida beach cottage experience! An Island vacation favorite, Anna Maria Beach Cottages preserves the charm of yesterday alongside modern conveniences. Snuggled just a few steps from the beach between Oak Avenue and Mangrove Avenue on Anna Maria Island’s gorgeous north-end, you’ll have the beach within reach, a cozy place to call home, and plenty of vacation adventures close by.brbrMade up of six buildings with eleven rental homes between them, Anna Maria Beach Cottages marries a homestyle atmosphere with resort-style service. The Cottages range from studio-size to three bedrooms, all including a kitchen. There is an on-site office, a heated pool, a picnic area with grills, beach chairs and umbrellas, bikes, onsite shared laundry and lovely landscaping along the paths from building to building. brbrGroup gatherings are welcome, including weddings, family reunions, and company getaways. And with a ground-level, ADA accessible unit, multi-generational families can include grandparents and great-grandparents to take part in family vacation memories that will last a lifetime.brbrFrom this prime location, you can walk, bike, or take the free Island Trolley to check out shops, art, restaurants, excursions, and more. Pine Avenue is the center of activity on the north end, just a few minutes away, with great food and fun shops leading up to the Anna Maria Island City Pier. The heart of Holmes Beach has a wide array of activities and sights for everyone in your group. And Bridge Street is located to the south in Bradenton Beach, home to a boardwalk-style, “walkable community.” brbrAlso well within driving distance for day trips to popular Florida destinations, it’s easy to check out theme parks in Orlando, the aquarium and zoo in Tampa, zip-lining in Bradenton, museums and culture in Sarasota, or getting close to nature at one of many nearby state parks.brbrWhether you’re looking for a quick trip to disconnect (perhaps a long one ), a fun-filled change of pace, or a romantic weekend, Anna Maria Beach Cottages has what you need for a memorable holiday. Reserve your memories today!

Flirty Flamingo Cottage Updated beach cottage, moments from the sand, w/pool!

Anna Maria, Florida, United States

Bed

Bath

Sleeps

$349.7

This rental is part of the Anna Maria Beach Cottages. More information on this charming property below!brbrCottage 110B is perfect for couples on a romantic Anna Maria Island vacation! One of the charming Anna Maria Beach Cottages, this is a studio vacation rental with a trellised entry deck and is only moments from the gorgeous white sands Anna Maria Island is famous for.brbrThe picturesque patio includes a sun-dappled table for two under a beautiful trellis, surrounded by tropical landscaping. Large windows let in the natural light, making this a bright and inviting place to relax, read a book, or watch a movie. This little studio includes everything you might need for a comfortable and memorable beach vacation, including a full kitchen, lounge area, queen bed, and full bathroom.brbrYou’ll also have access to all the amenities the Anna Maria Beach Cottages has to offer, including a heated pool with a lounge area, assorted beach gear, bikes, picnic and grilling area, onsite laundry and an on-site office for area information and support during your stay. Continue reading for more about this sweet and enchanting place!brbrbrPlease note that pets are not allowed in this rental.brbrbrABOUT ANNA MARIA BEACH COTTAGESbrbrBe whisked away to an Old Florida beach cottage experience! An Island vacation favorite, Anna Maria Beach Cottages preserves the charm of yesterday alongside modern conveniences. Snuggled just a few steps from the beach between Oak Avenue and Mangrove Avenue on Anna Maria Island’s gorgeous north-end, you’ll have the beach within reach, a cozy place to call home, and plenty of vacation adventures close by.brbrMade up of six buildings with eleven rental homes between them, Anna Maria Beach Cottages marries a homestyle atmosphere with resort-style service. The Cottages range from studio-size to three bedrooms, all including a kitchen. There is an on-site office, a heated pool, a picnic area with grills, beach chairs and umbrellas, bikes, onsite shared laundry and lovely landscaping along the paths from building to building. brbrGroup gatherings are welcome, including weddings, family reunions, and company getaways. And with a ground-level, ADA accessible unit, multi-generational families can include grandparents and great-grandparents to take part in family vacation memories that will last a lifetime.brbrFrom this prime location, you can walk, bike, or take the free Island Trolley to check out shops, art, restaurants, excursions, and more. Pine Avenue is the center of activity on the north end, just a few minutes away, with great food and fun shops leading up to the Anna Maria Island City Pier. The heart of Holmes Beach has a wide array of activities and sights for everyone in your group. And Bridge Street is located to the south in Bradenton Beach, home to a boardwalk-style, “walkable community.” brbrAlso well within driving distance for day trips to popular Florida destinations, it’s easy to check out theme parks in Orlando, the aquarium and zoo in Tampa, zip-lining in Bradenton, museums and culture in Sarasota, or getting close to nature at one of many nearby state parks.brbrWhether you’re looking for a quick trip to disconnect (perhaps a long one ), a fun-filled change of pace, or a romantic weekend, Anna Maria Beach Cottages has what you need for a memorable holiday. Reserve your memories today!

Apartment

Anna Maria Beach Cottage 110B Updated studio beach cottage, steps to the sand!

Anna Maria, Florida, United States

Bed

Bath

Sleeps

$380.47

This rental is part of the Anna Maria Beach Cottages. More information on this charming property below!brbrCottage 110G is the perfect place for a small family or a couples’ getaway on Anna Maria Island! One of the charming Anna Maria Beach Cottages, this recently remodeled 1 bed/1 bath ground-level vacation home is close to the beautiful pool deck and only moments to the turquoise water of the Gulf beach.brbrThis cozy rental features a front patio, corner kitchen, dining area, living room, and private bedroom. A trellis over the patio and the surrounding hibiscus offers a sun-dappled and welcoming place to enjoy a meal or just relax in the fresh Florida air. brbrThe master suite includes a queen bed with a spacious en-suite bathroom, complete with a walk-in shower. The overstuffed sofa in the living room isn’t just for sinking into after a long day of sun and sand, it’s also a sleeper sofa, providing sleeping space for two more guests.brbrYou’ll also have access to all the amenities the Anna Maria Beach Cottages has to offer, including a heated pool with a lounge area, assorted beach gear, bikes, picnic and grilling area, onsite laundry and an on-site office for area information and support during your stay. Continue reading for more about this sweet and enchanting place!brbrbrPlease note that pets are not allowed in this rental.brbrbrABOUT ANNA MARIA BEACH COTTAGESbrbrBe whisked away to an Old Florida beach cottage experience! An Island vacation favorite, Anna Maria Beach Cottages preserves the charm of yesterday alongside modern conveniences. Snuggled just a few steps from the beach between Oak Avenue and Mangrove Avenue on Anna Maria Island’s gorgeous north-end, you’ll have the beach within reach, a cozy place to call home, and plenty of vacation adventures close by.brbrMade up of six buildings with eleven rental homes between them, Anna Maria Beach Cottages marries a homestyle atmosphere with resort-style service. The Cottages range from studio-size to three bedrooms, all including a kitchen. There is an on-site office, a heated pool, a picnic area with grills, beach chairs and umbrellas, bikes, onsite shared laundry and lovely landscaping along the paths from building to building. brbrGroup gatherings are welcome, including weddings, family reunions, and company getaways. And with a ground-level, ADA accessible unit, multi-generational families can include grandparents and great-grandparents to take part in family vacation memories that will last a lifetime.brbrFrom this prime location, you can walk, bike, or take the free Island Trolley to check out shops, art, restaurants, excursions, and more. Pine Avenue is the center of activity on the north end, just a few minutes away, with great food and fun shops leading up to the Anna Maria Island City Pier. The heart of Holmes Beach has a wide array of activities and sights for everyone in your group. And Bridge Street is located to the south in Bradenton Beach, home to a boardwalk-style, “walkable community.” brbrAlso well within driving distance for day trips to popular Florida destinations, it’s easy to check out theme parks in Orlando, the aquarium and zoo in Tampa, zip-lining in Bradenton, museums and culture in Sarasota, or getting close to nature at one of many nearby state parks.brbrWhether you’re looking for a quick trip to disconnect (perhaps a long one ), a fun-filled change of pace, or a romantic weekend, Anna Maria Beach Cottages has what you need for a memorable holiday. Reserve your memories today!

Condo

Anna Maria Beach Cottage 110G Updated beach cottage, with pool and beach gear!

Anna Maria, Florida, United States

Bed

Bath

Sleeps

$5787.3

The Starfish Cottage has been recently renovated while maintaining all the charm of an old Florida Key West style bungalow. Enjoy the new private heated pool with lush tropical setting. The new kitchen provides plenty of storage , a full sized refrigerator and freezer, dishwasher, range and microwave. There's also an outdoor grill. The large screened in porch features a vaulted ceiling, large ceiling fans, plenty of seating including rocking chair and swing bench. On the porch a dining table accommodates 8 and a small bistro table seats 2. brbrInside you'll find an open concept living space where dining area, kitchen and living room have been newly furnished with luxurious deep seat couches and lounge chairs, original hardwood floors add to the charm. Fresh linens, bath and beach towels are provided along with basic toiletries. Decor has been collected over time and obtained from local artists for a unique old Florida style.brbrDown the hall you'll find two comfortable bedrooms, each with a queen-size bed and large closets. The Master bathroom has been newly updated. Another full bathroom is conveniently located in the hall. Climb up the spiral staircase to the quaint loft which has 2 twin beds.brbrThe cottage is in a terrific location, immediately east of Gulf Drive, a quick 200-yard walk will bring you right to the white-sand beach. With Pine Avenue and the village of Anna Maria 2 short blocks to the north, you can walk to everything. Pine Avenue offers restaurants, shopping, community theater, historic Roser Church, and the Anna Maria Historical Society Museum. A free trolley is available to get you around the entire island all the way south to Coquina Beach. Scooter and golf cart rentals are located within 100 yards.brbrFree WiFi, flatscreen cable/smart TV, deluxe wireless bluetooth speaker, books, and board games provide entertainment, while a private washer/dryer lets you take care of laundry. Keyless entry at the front door ensures easy access and security. The driveway has space to park four vehicles.brbrA NOTE ABOUT CHILDREN: Kids love the loft area. However, the spiral staircase could be dangerous for younger children. Therefore, this property is not recommended for children under 8 years old.

Charming cottage with heated pool, tropical landscaping in prime location.

Anna Maria, Florida, United States

Bed

Bath

Sleeps

$1144.71

NO CANCELLATION FEES: br$500 deposit due at time of booking; balance due 60 days prior to arrival brCancel 60+ days before arrival → Full refund (no fees). brCancel within 60 days of arrival → No refund. brCancellations must be made in writing and received by Beach Retreats on or before the 60-day deadline. Once paid, it's non-refundable. brExtended stays (over 2 weeks) or bookings over $20,000 → Full payment due 90 days before arrival; once paid, it's non-refundable. Third-party travel insurance purchased through Beach Retreats is non-refundable. For reservations 21+ nights or $20,000+ → 10% deposit due at time of booking. brThird party travel insurance cost is due at time of purchase brbrWritten notice is required to cancel a reservation; an email from the address associated with the reservation is acceptable as written notice.brbrbrIf Guest needs to shorten their stay or change to a different property, the normal cancellation policy applies. No changes are permitted during the stay.brbrAt A GlancebrbrJust a hop, skip and a jump From The BeachbrGulf ViewsbrPrivate Heated PoolbrContactless EntrybrGas BBQ Grillbr2 Car GaragebrParking for 4brFully Equipped KitchenbrJust under 2000 Sq feet of completely remodeled luxurybrTwo Streets from Pine Ave- The Donut Experiment, The Waterfront, Popos, and all of the unique shops for souvenir searching!brOn our Professional Linen Service ProgrambrOverviewbrbrGulf Shore Retreatbrbr210 Sycamore AvenuebrbrAnna Maria, FL 34216brbrGulf Shore Retreat is a stunning four-bedroom, four-bathroom home that comfortably sleeps 8 and can accommodate up to 10 guests. It is located in the city of Anna Maria and is just a few houses from the beach! Take in views of the Gulf waters from the top floor or grab your beach gear and stroll to the turquoise waters of Anna Maria Island and Bean Point. Whether it's sun tanning by the pool or catching an afternoon nap in the breezy, covered patio; the moment you set foot in Gulf Shore Retreat you'll be whisked away to vacation mode. brbr While most of our properties rent only from Saturday to Saturday, exceptions can be made. Please reach out to us prior to booking if you would like to arrive or depart on alternate dates, or stay for fewer than 7 nights. We would love to host you!brbrThis home has an open floor plan and a massive common area that is flooded with natural light. The kitchen is expansive and features stunning marble countertops and white custom cabinetry, a full suite of stainless-steel appliances, and a massive marble island that includes a breakfast bar. The living room is elegantly decorated and offers access to a large balcony with seating overlooking the pool; both are perfect places to relax together after a day spent in the sun.brbrAll four bedrooms have flat-screen TVs, three of the four bedrooms have private en-suite bathrooms, and all of the bedrooms on the main level have access to their own private balcony! There's nothing better than a vacation with friends and family, but having a little space to chill out in private is also much needed. This house allows for both! Enjoy your friends and family in all the shared areas inside and out. When you need a little down time, simply retreat to your gorgeous, private bed and bathroom to relax and refresh.brbrThe pool area has been designed with vacation in mind and ideally built to take full advantage of the weather in Florida. Getting back from the beach Rinse off in your private outdoor shower and continue sunbathing on the many poolside lounge chairs. Chill out in your covered outdoor lounge and dining area. brbrThere are so many features that make this home unique! Some of it's most impressive highlight are: additional refrigerator in the garage and a full-sized ice maker. Headed to the beach No need to grab bags of ice, you can simply fill your cooler in the garage and keep your poolside snacks and beverages at hand in the additional fridge!brbrWe do our rentals from Saturday to Saturday, if you are looking for a stay that is not a 7-night rental or would like to begin your vacation on a day other than Saturday please send us an email to reservations@beachretreatsfl.com as we can sometimes accommodate alternate reservations brbrWe might be only 7 miles long but Anna Maria has everything you could possibly need for your perfectbrbeach vacation. Traveling with a little one All our homes come with pack & plays and highchairs. Needbrmore There are several great rental places that have everything from baby gates to golfcarts, and theybrwill drop them right off at your vacation property for you. No need to pack beach towels we providebrthose for you.brRemember we are laid back and on Island time - Flip-flops and shorts are ok for breakfast, lunch andbrdinner no need to overpack you will most likely be in your cutest bathing suit or bikini anyways.brNo need to pay the crazy high fees to check all those bags! With Publix, CVS, and Walgreens right on thebrisland you can grab any sunscreen, hair product anything needed, why haul it all with you brbrBedrooms & BathroomsbrbrSLEEPING ARRANGEMENTS:brbrPrimary Bedroom: Main Floor - KingbrSecond Bedroom: Main Floor - KingbrThird Bedroom: Top Floor - KingbrFourth Bedroom: Main Floor - KingbrbrBATHROOMS:brbrPrimary En-Suite: Walk-in Shower - Double Vanity – Main FloorbrSecond En-Suite: Walk-in Shower - Single Vanity – Main FloorbrThird En-Suite: Walk-in Shower - Single Vanity – Top FloorbrFourth Bathroom: Walk-in Shower - Single Vanity – Main FloorbrbrExteriorbrbrNot only is this home so close to the beach, but it also has a great north-end location that's easy walking distance to so many of Anna Maria Island's best activities. Take a stroll over to nearby restaurants and shops on Pine Avenue or spend the afternoon fishing at the City Pier.brbrOur pools are heated during the months of November through April at no additional charge to our guests. We do not heat the pools during the warmer months of May through October. Pools are heated to a temperature of 84 degrees. However, please be aware that even in Southwest Florida we do occasionally get cold spells that can send the temperatures down into the 30's for a few nights in a row. This will cause the pool water temperature to draw down to in the 70's and a pool pump will automatically shut down if the outside temperature gets too cold. When the weather gets warmer and the pumps are able to re-engage, please be mindful that re-heating of the pool back to 84 degrees may take several days depending on the severity of the cold spell. Ultimately, these situations are beyond our control. Other issues such as severe weather conditions, equipment malfunction, temporary loss of use of equipment or amenities due to maintenance purposes or other items do happen from time to time. All of our pools and pool equipment are closely monitored by the pool companies. For your safety, we kindly ask that the controls not be tampered with -most of the systems are locked for this reason. Due to the island's strict 10pm noise ordinance, the pool heaters will not run overnight. Please remember, outdoor spas are not hot tubs. Please be aware that Beach Retreats does not issue refunds based on acts of god. However, please know that in the rare event of pool equipment malfunction during your stay, AMV will do everything in our power to expedite repairs as quickly as possible as we certainly want you to enjoy your heated pool and Florida sunshine to the fullest extent possible!brbrAmenitiesbrbrExteriorbrbrGas Grill • Private Pool • Covered Parking • Garage • Deck / Patio • Outdoor Living Area • Fenced Yard • Outdoor Shower • BalconybrbrGeneralbrbrNew Rental • Luxury • Linen ServicebrbrInteriorbrbrFree Wi-Fi • Cable/Satellite • Air Conditioning • Washer • Dryer • Dishwasher • Television • Full KitchenbrbrProximitybrbrClose to the Gulf • Gulf View brbrNo cancellation fees!brCancel 60+ days before arrival → Full refundbrCancel within 60 days → No refundbrExtended stays & bookings $20,000+ → Full payment 90 days prior, non-refundablebr$500 deposit due at booking; balance due 60 days priorbrThird-party travel insurance through Beach Retreats is non-refundablebrNo changes permitted within 60 days of arrival or during staybrWe highly recommend cancelation insurance br This home can accommodate up to 3 vehicles

Gulf Shore Retreat: Private Pool managed by Beach Retreats FL Anna Maria Island

Anna Maria, Florida, United States

Bed

Bath

Sleeps

$366.95

Summary:brBay Breeze Cottages is an Old Florida Charm Boutique Resort located on historic Anna Maria Island. Bask in the endless sun all year long, take a swim in our private heated pool with your favorite beverage, or head out anywhere on the island in our street legal gas powered golf carts to any of the local restaurants, piers, sand white sand beaches, and all other attractions the island has to offer. Come enjoy your own slice of paradise at Bay Breeze Cottages on Anna Maria Island.brbrThe Space:brEach Cottage has a fully renovated kitchen, bath, and living area. Each cottage has a full kitchen with brand new stainless steel appliances including: full sink, faucet, garbage disposal, cook tops, ovens, microwaves, dishwasher, and refrigerator. Exquisite granite counter tops with custom hand carved wood shelves and built in wooden cutting boards are standard. Each renovated bathroom has a new toilet, vanity, custom deluxe shower head, and vanity tiles. The bedroom includes brand new Beauty Rest Queen bed and high quality Queen pull out sofa, new 32 inch flat screen HD tv's, custom wood floors and wood ceilings throughout.brbrGuest Access:brUpon booking one of our cottages, you will receive a welcome email with the access code for the electronic key lock on the entry door plus a secondary code for the lock box which contains the physical keys as a back up.brbrThe Neighborhood:brThe North end of Anna Maria Island is the most desirable location on the entire island. PARADISE would best describe the surrounding areas of Bay Breeze Cottages. White Sandy Beaches, Two Piers, Aquatic Life such as Dolphins, Manatees, and Pelicans can be seen daily. The North end of Anna Maria has the best restaurants, shops, bars, and other tourist attractions.brbrGetting Around:brIncluded in your stay are street legal golf carts & beach cruiser bicycles which allow you to venture out to the entire island with convenience & ease. Public parking is plentiful throughout the island at all local establishments and attractions.brbrOther Things to Note:brAmenities and Location are what truly separate Bay Breeze Cottages from all other resorts on the island. Our Amenity Package is worth on average $1,000 to $1,500 dollars for the week if you were to rent separately. Check our Comparison sheet in our photos section for reference.brbrLocation! Location! Location! Bay Breeze Cottages is located on the highly desirable North end of Anna Maria Island. We are just steps from the famous Rod & Reel Pier, Anna Maria City Pier, White Sandy Beaches, Shops, Restaurants, Bars, and other local attractions. Our included amenity package will save guests an average of $1,000 to $1,500 based on one week's stay.brbrInteraction with Guests:brWe are always here to answer any questions you may have during your stay and we are always accessible to our guests.

Bay Breeze Cottages #1 (The Mahi-Mahi)

Anna Maria, Florida, United States

Bed

Bath

Sleeps

$1395.48

Go with the Flow by Exclusive VacationsbrVacation Rental License #VR24-000026brbrWelcome to Go with the Flow, an exceptional three-level luxury retreat offering five bedrooms and five and a half bathrooms, thoughtfully designed for an elevated Anna Maria Island getaway. Located just a short five-minute stroll to Anna Maria Beach, this newly built vacation home showcases a private pool with spa, a rooftop entertainment deck, and beautifully curated designer interiors. Whether gathering with family or celebrating time away with friends, every detail of this stunning home is designed to create an unforgettable island experience from sunrise to sunset.brbrHighlightsbr• 5-minute walk to Anna Maria Beachbr• 5 Bedroom / 5.5 Bath luxury homebr• 4 King Beds, 2 Twin over Twin Bunk Bedsbr• Private pool with in-ground spabr• Rooftop entertainment deck with barbr• 3-in-1 game table (pool, ping pong, air hockey)br• Outdoor lounge areabr• Chef’s kitchen with wine refrigeratorbr• Washer and dryerbr• Parking for 4 vehiclesbr• Pet friendly with host approvalbrbrStep into your private outdoor oasis where a resort style river pool and in-ground spa create the perfect setting for relaxation and entertainment. The rooftop deck provides an elevated gathering space with sweeping island views, comfortable seating, a bar setup, and a versatile 3 in 1 game table that brings everyone together for evenings of laughter and fun. Whether enjoying sunny afternoons poolside or unwinding beneath the stars on the rooftop, every outdoor space invites you to slow down and savor island life.brbrInside, the home blends refined coastal design with modern comfort. The open concept living area features plush seating, accent chairs, and a large television, creating an inviting space for relaxing evenings. The chef inspired kitchen is equipped with high end appliances, quartz countertops, and a wine refrigerator, making meal preparation effortless, while the spacious dining table and bar seating provide the perfect place for gathering and sharing meals.brbrEach bedroom offers a peaceful private retreat, complete with crisp linens, televisions, and its own ensuite bathroom. The primary suite is a true sanctuary featuring a king bed, private balcony access, and a spa inspired bathroom with a soaking tub, double vanity, and walk-in shower. Three additional king suites include ensuite bathrooms with walk-in showers, providing comfort and privacy for every guest. The bunk room, ideal for younger travelers or teens, features two twin over twin bunk beds and an ensuite bathroom with a shower and tub combination. A washer and dryer are also available for added convenience during extended stays.brbrExclusive Vacations Amenitiesbr• 6-seat Club Car Cru luxury golf cartbr• Premium beach cruiser bikesbr• Luxury beach chairs, umbrellas, and beach cartbr• Upgraded bed and bath linens with premium bath amenitiesbr• Fully stocked starter supplies for a seamless arrivalbr• Portable Pack and Play for traveling familiesbrbrRoom Detailsbr- Primary Bedroom: King bed and ensuite bathroom with standalone soaking tub and walk-in showerbr- Second Bedroom: King bed and ensuite bathroom with walk-in showerbr- Third Bedroom: King bed and ensuite bathroom with walk-in showerbr- Fourth Bedroom: King bed and ensuite bathroom with walk-in showerbr- Fifth Bedroom: Two Twin over Twin bunk beds and ensuite bathroom with shower and tub combinationbrbrGo with the Flow offers everything needed for a seamless and elevated island stay, enhanced by the exclusive amenities included with your reservation. Guests enjoy access to a 6-seat Club Car Cru golf cart for easy island exploring, luxury beach cruiser bikes, and a full set of premium beach gear including chairs, umbrellas, and a beach cart for effortless days on the sand. Inside, upgraded bed and bath linens, premium toiletries, and fully stocked starter supplies create a comfortable, hotel quality experience, while a portable Pack and Play provides added convenience for traveling families. Its prime location places you moments from the best of Anna Maria Island, where you can bike to the boutiques of Pine Avenue, dine at locally loved restaurants, or hop on the free island trolley to explore the island from north to south.brbrDesigned for guests seeking both relaxation and refined island living, this exceptional home captures the very best of Anna Maria Island. Reserve your stay today and experience the art of effortless luxury with Exclusive Vacations.brbrbr- brWith 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 Exclusive Vacations Rental Policies for full details. brbrUse of the provided golf cart requires the driver to maintain a current U.S. automobile insurance. Proof of insurance is required upon request.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. brbrThis home is managed by Exclusive Vacations, 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 see our Exclusive Vacations 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.

Experience Luxury at Go with the Flow! Lazy River Pool, Rooftop Deck and Games!

Anna Maria, Florida, United States

Bed

Bath

Sleeps

$1055.29

The James by AMI Locals brbrWelcome to The James by AMI Locals, your ultimate North End beach getaway on Anna Maria Island. This brand-new four bedroom, four and a half bath luxury home is just a short six-minute walk from the island’s world-famous Gulf beaches and offers a rooftop deck with stunning Gulf views, a private pool with spa, and resort-style outdoor living. Designed for families and groups, The James delivers a seamless blend of modern elegance and laid-back coastal charm, perfect for those who want to unwind in style just moments from Pine Avenue’s boutiques and waterfront dining. brbrHighlights br• 6-minute walk to the beach br• 4 Bedrooms / 4.5 Bathrooms br• 3 King beds, 1 Full bed, 1 Full sleeper sofa br• Private pool with spa and swim-up bar seating br• Rooftop deck with beach views br• Ping pong and cornhole br• Beach chairs and beach cart for guest use br• Outdoor living space with dining area and TV br• 4 parking spaces brbrThe outdoor space at The James feels like your own private resort. Enjoy the heated pool with spa, swim-up bar seating, and sunshelf, surrounded by luxe lounge chairs for soaking up the sun. The covered patio includes a dining area, cozy seating, outdoor TV, and BBQ grill for outdoor meals and evening gatherings. As the sun sets, head to the rooftop deck to take in sweeping Gulf views and toast another perfect day on Anna Maria Island. brbrStep inside to a bright, open concept floor plan where modern coastal design meets comfort. The living area features a chic seating arrangement, TV, and sliding doors that fill the space with natural light. The fully equipped kitchen includes stainless steel appliances, an island with barstools, and a formal dining table for family meals. Whether you’re cooking breakfast or hosting a sunset dinner, this stylish space makes gathering easy and enjoyable. brbrEach bedroom is a private retreat complete with plush bedding, televisions, and ensuite bathrooms. br The primary suite showcases a king bed, private balcony, and ensuite bathroom with dual vanities and a walk-in shower. The second and third king bedrooms feature ensuite bathrooms with walk-in showers, while the fourth bedroom includes a full bed and ensuite bathroom with shower/tub combo. A den near the rooftop access offers a full sleeper sofa, providing additional space for guests or kids. brbrRoom Details br-Primary Bedroom: King bed, balcony, ensuite bathroom with walk-in shower br-Second Bedroom: King bed, ensuite bathroom with walk-in shower br-Third Bedroom: King bed, ensuite bathroom with walk-in shower br-Fourth Bedroom: Full bed, ensuite bathroom with shower/tub combo br-Den: Full sleeper sofa brbrThis home also includes Wi-Fi, a laundry room, and all the essentials for a comfortable stay. Located on the coveted North End of Anna Maria Island, The James places you within easy walking distance of Bean Point Beach, Bayfront Park, and Pine Avenue, where you can explore island boutiques, cafes, and restaurants. brbrWith breathtaking rooftop views, designer interiors, and resort-style amenities, The James by AMI Locals is the perfect setting for your next luxury island getaway. Enjoy modern comfort, privacy, and convenience just steps from the beach and all the charm of Anna Maria Island’s North End. Book your stay at The James by AMI Locals today and experience island living at its finest! brbr- brThis property does not allow pets of any kind. br4 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. brThis home is managed by AMI Locals, an Anna Maria Island property management company. brWe 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. brPlease see our AMI Locals Rental Policies for full details. brPlease 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.

AMI Escape! Swim-Up Bar, Ping Pong, Spa and Walk to Beach

Anna Maria, Florida, United States

Bed

Bath

8

Sleeps

$781.81

Welcome to the Pelican Suite at AMI Beach Lagoon Resort, your lakefront luxury retreat on Anna Maria Island.brbrLocated at 604 North Shore Drive in the highly desirable north end of Anna Maria near Bean Point, this 12,500 sq ft property uniquely combines Gulf beach access with private lakefront living on Vista Lake. The Gulf beach is just a short walk across North Shore Drive.brbrThe resort consists of three separate ground-level suites that may be rented together or individually:brbr- The Turtle Suite – 1 bedroom, 1 bathroom (Sleeps 2)brbr- The Manatee Suite – 3 bedrooms, 2 bathrooms (Sleeps 6)brbr- The Pelican Suite – 3 bedrooms, 2 bathrooms (Sleeps 6)brbrThe Turtle Suite (front house facing North Shore Drive) offers one bedroom, while the Manatee and Pelican Suites (rear house facing Vista Lake) each offer three bedrooms. Each suite has its own private entrance, fully equipped kitchen, outdoor seating area, and grill. When multiple suites are rented separately, the pool deck and certain outdoor amenities are shared.brbrIn this 2-bedroom rental configuration, the lakeside bedroom of the full 3-bedroom suite remains locked and is not rented to other guests. You will have the entire unit completely to yourself; all outdoor areas and shared amenities (pool, spa, dock, kayaks, putting green, seating areas etc.) remain available for use by guests of the other suites as well.brbrAt the heart of the property is the large, Mickey Mouse-shaped heated saltwater pool with attached spa, creating a true resort-style atmosphere. brbrPool and spa cannot be heated simultaneously, and heating performance is weather dependent and subject to environmental and technical limitations.brbrThe spa is available daily between 1:00 PM and 10:00 PM only. The system can operate either the pool or the spa, but not both at the same time; extended spa use stops pool circulation and heating and negatively affects water quality. Operation outside these hours is not possible.brbrDue to local noise ordinances, pool and spa equipment shuts off overnight. Pool and spa are provided as amenities for guest enjoyment and do not constitute grounds for refund or compensation in the event of limited operation or downtime.brbrThe private dock on Vista Lake invites guests to fish, observe manatees, or explore the water using the provided kayaks. Additional outdoor amenities include a putting green, giant life-size chess board, multiple covered seating areas, grills, beach carts, and beach chairs.brbrAll suites are ground-level with wide doors and low-threshold showers, providing comfortable accessibility for guests of all ages. Each unit includes high-speed WiFi, dishwasher, and full-sized washer and dryer.brbrFlorida’s climate can bring high temperatures and humidity, especially during summer months. The air conditioning systems are professionally maintained and operate within regulated performance ranges to ensure reliable and consistent indoor comfort throughout your stay.brbrYou are vacationing in a residential neighborhood. Please be a good neighbor by keeping noise at a respectful level, particularly around the pool and outdoor areas. Excessive or unreasonable noise is prohibited by local ordinances.brbrDue to documented health considerations within the Owner’s family, pets — including service or emotional support animals — are not permitted on this private property under any circumstances. This includes visitors of Guests. Any animal found on the premises will result in expedited eviction, forfeiture of payments, and liability for specialized cleaning and any resulting damages.brbrExterior video surveillance with motion-activated recording is installed in the driveway, pool equipment zones, pool deck, kayak rack and lakefront areas. No cameras are installed inside any building.brbrThe property was completely renovated in 2021. Environmentally friendly solar roofs were added in 2022. Following the 2024 storm season, exterior landscaping and select technical components were renewed and upgraded. Due to extensive preventive measures installed in advance, no interior water intrusion occurred.brbrWe encourage guests to consider purchasing travel insurance to protect their stay against unforeseen circumstances.brbrAdditional AMI Beach Vacation properties on Vrbo: #1303019, #2243665, #2243667, #2243668, #4924163, #4928637, #4928638, #4928639, #4938653, #4938654, #4952711, #4952712.

Resort-Style Ground Floor 2BR Pelican Suite, Heated Pool / Spa, Lakefront

Anna Maria, Florida, United States

2

Bed

2

Bath

Sleeps

$822.45

Welcome to the Manatee Suite at AMI Beach Lagoon Resort, your lakefront luxury retreat on Anna Maria Island.brbrLocated at 604 North Shore Drive in the highly desirable north end of Anna Maria near Bean Point, this 12,500 sq ft property uniquely combines Gulf beach access with private lakefront living on Vista Lake. The Gulf beach is just a short walk across North Shore Drive.brbrThe resort consists of three separate ground-level suites that may be rented together or individually:brbr- The Turtle Suite – 1 bedroom, 1 bathroom (Sleeps 2)brbr- The Manatee Suite – 3 bedrooms, 2 bathrooms (Sleeps 6)brbr- The Pelican Suite – 3 bedrooms, 2 bathrooms (Sleeps 6)brbrThe Turtle Suite (front house facing North Shore Drive) offers one bedroom, while the Manatee and Pelican Suites (rear house facing Vista Lake) each offer three bedrooms. Each suite has its own private entrance, fully equipped kitchen, outdoor seating area, and grill. When multiple suites are rented separately, the pool deck and certain outdoor amenities are shared.brbrIn this 2-bedroom rental configuration, the lakeside bedroom of the full 3-bedroom suite remains locked and is not rented to other guests. You will have the entire unit completely to yourself; all outdoor areas and shared amenities (pool, spa, dock, kayaks, putting green, seating areas etc.) remain available for use by guests of the other suites as well.brbrAt the heart of the property is the large, Mickey Mouse-shaped heated saltwater pool with attached spa, creating a true resort-style atmosphere. brbrPool and spa cannot be heated simultaneously, and heating performance is weather dependent and subject to environmental and technical limitations.brbrThe spa is available daily between 1:00 PM and 10:00 PM only. The system can operate either the pool or the spa, but not both at the same time; extended spa use stops pool circulation and heating and negatively affects water quality. Operation outside these hours is not possible.brbrDue to local noise ordinances, pool and spa equipment shuts off overnight. Pool and spa are provided as amenities for guest enjoyment and do not constitute grounds for refund or compensation in the event of limited operation or downtime.brbrThe private dock on Vista Lake invites guests to fish, observe manatees, or explore the water using the provided kayaks. Additional outdoor amenities include a putting green, giant life-size chess board, multiple covered seating areas, grills, beach carts, and beach chairs.brbrAll suites are ground-level with wide doors and low-threshold showers, providing comfortable accessibility for guests of all ages. Each unit includes high-speed WiFi, dishwasher, and full-sized washer and dryer.brbrFlorida’s climate can bring high temperatures and humidity, especially during summer months. The air conditioning systems are professionally maintained and operate within regulated performance ranges to ensure reliable and consistent indoor comfort throughout your stay.brbrYou are vacationing in a residential neighborhood. Please be a good neighbor by keeping noise at a respectful level, particularly around the pool and outdoor areas. Excessive or unreasonable noise is prohibited by local ordinances.brbrDue to documented health considerations within the Owner’s family, pets — including service or emotional support animals — are not permitted on this private property under any circumstances. This includes visitors of Guests. Any animal found on the premises will result in expedited eviction, forfeiture of payments, and liability for specialized cleaning and any resulting damages.brbrExterior video surveillance with motion-activated recording is installed in the driveway, pool equipment zones, pool deck, kayak rack and lakefront areas. No cameras are installed inside any building.brbrThe property was completely renovated in 2021. Environmentally friendly solar roofs were added in 2022. Following the 2024 storm season, exterior landscaping and select technical components were renewed and upgraded. Due to extensive preventive measures installed in advance, no interior water intrusion occurred.brbrWe encourage guests to consider purchasing travel insurance to protect their stay against unforeseen circumstances.brbrAdditional AMI Beach Vacation properties on Vrbo: #1303019, #2243665, #2243666, #2243667, #2243668, #4924163, #4928637, #4928638, #4928639, #4938653, #4938654, #4952711, #4952712.

Resort-Style Ground Floor 2BR Manatee Suite, Heated Pool / Spa, Lakefront

Anna Maria, Florida, United States

Bed

Bath

Sleeps

$256.47

Photos Updated March 2025! brbrLooking for a cozy, budget-friendly escape just steps from the beach The Twins is the spot for you! This charming 2-bedroom, 2-bathroom vacation rental is nestled less than a block from the stunning Anna Maria Island shoreline – just eight houses away. Whether you're planning lazy beach days or sunset strolls, the sandy shores are practically at your doorstep. brbrConvenience is key at The Twins. The Free Island Trolley stop is only one house away, making it a breeze to explore all of Anna Maria Island without the hassle of driving. You'll also love being within walking distance of local restaurants, unique shops, and the vibrant Pine Avenue, where you can enjoy everything from fresh seafood to quaint boutiques. brbrThe Twins is all about comfort and simplicity. This clean and well-maintained home offers everything you need for a relaxed beach vacation without any unnecessary frills. It's the perfect place to unwind after a day of sun and sand. brbrReady to experience the laid-back island lifestyle Book your stay at The Twins today!brbrPETS: LIMIT 1 PET. Small dogs are considered with prior approval. Must be well trained and less than 35lbs. 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.

The Twins: Your Perfect Budget Beach Getaway!

Anna Maria, Florida, United States

Bed

Bath

Sleeps

$1128.52

CabAnna Maria is a newly renovated 4 bedroom, 4.5 bath house, that sleeps 8 (max) comfortably, a quick 450 ft to the pristine sands of AMI beach. 3 king bedrooms w/ en-suite baths and large TVs. 4th bedroom has a twin over full bunk. Common bath has a tub. Open spacious living room w/large comfy couch and a 75` TV. 1/2 bath on pool level, cabana with TV, sink & fridge. Beach chairs, umbrellas, bikes, SUP, kayak & more. Linens, beach towels and toiletries provided. Too much to list!brbrThe property does have a downstairs apartment and garage that we use and don`t rent out. There are no shared walls and the backyard is completely private for your enjoyment! In the off chance that you see us, don`t hesitate to say hi!brbrAsk us about our long-term stay discount!brbrManaged by Doreste PropertiesbrNo smoking. Before booking with a pet, please reach out to owner for breed restrictions.

CabAnna Maria Beach Block 4 Bedroom 4.5 Bath

Anna Maria, Florida, United States

Bed

Bath

Sleeps

$709.32

New to the rental inventory and awaiting your stay! brbrThis Island home is a Charming, mix of modern + vintage with many updates and 8 houses from the gorgeous Gulf Beaches!! This 4 bedroom, 4 bathroom home is the perfect location in the City of Anna Maria and only 3 blocks away from Pine Avenue with boutiques and restaurants. brbrAs soon as you walk through the front gates, you are greeted by an outdoor lounge area with a fabulous outdoor entertainment area with putting green, shuffleboard court, corn hole and outdoor lights. Just beyond is a beautiful pool and spa with a water feature . It is very secluded and private, its like your own little retreat with lush landscaping completely surrounding. brbrThe interior details of this home is something like you have never seen, classic vintage pieces mixed with modern touches and gorgeous chandeliers throughout the home. The stairs have stunning blue tiles and steps, the little details are around every corner and pops of color throughout. There is new flooring throughout, ideal for beach living. The kitchen is light and bright with open shelving, large farm sink, new quartz countertops, and backsplash wall.brbrMore upgrades include 3 new bathrooms with new showers and countertops, dusk to dawn copper landscape lighting. You will love the natural light that comes through to the open concept living area where there is plenty of space for entertainment. Enjoy the gulf breeze on your front balcony that is directly off the living and dining room. There is another private small balcony off the primary bedroom on the top floor. brbrThere is plenty of room for the family with 2 primary bedrooms with ensuite bathrooms, one with a King bed and the other with a Queen bed. The 3rd bedroom has a King bed and the 4th bedroom has 2 sets of twin bunk beds. The dining area has seating for 8. brbrThis home has plenty of outdoor fun for the family including a basketball hoop! You will love the convenience of the outside shower and changing room just off the pool area with a mini fridge and stools.brbrWe look forward to hosting you!brbrMax Occupancy 8. Non-Smoking Unit. brbrMinimum Age to rent 25. All guests occupying a property who are under the age of 25 must be accompanied by a parent or legal guardian.brbrFran Maxon Real Estate is not responsible for pool temperatures, closures or malfunctions. No credit, discount and/or rate adjustment can be granted for items mentioned above or circumstances beyond our control. There will be days when the weather conditions will not allow pool heaters to accommodate swimming and temperature recovery times will vary. brbrPer the City Noise Ordinance: Quiet hours are to be observed between the hours of 10 pm to 8 am daily. This includes noise at the pool area. Please be especially mindful of loud music and loud voices when in and around pools or outdoor areas. Please refer to the rental agreement for further details and possible citations.brThis locations driveway is monitored by wireless surveillance.

Fun Family Home close to beach, Pool, outdoor games, beach gear

Anna Maria, Florida, United States

Bed

Bath

Sleeps

$1331.33

Siena Sky by Anna Maria Island Accommodations brbrWelcome to Siena Sky, a four-bedroom, four-bath luxury vacation home just steps from the beach. This stunning island getaway combines modern elegance with relaxed coastal comfort, featuring a rooftop deck with Gulf views, a heated pool and spa, and a prime location within walking distance of Pine Avenue, Bean Point, and the island’s best shops and restaurants. Perfect for families and groups, Siena Sky delivers the ultimate Anna Maria Island vacation experience. brbrHighlights br• 1-minute walk to Anna Maria City Beach br• 4 Bedrooms / 4 Bathrooms br• 3 King beds, 2 Twin-over-Twin bunk beds br• Rooftop deck with Gulf views br• Brand new construction br• Heated pool with spa br• Elevator access br• Covered patio with seating and BBQ grill br• Pet-friendly with approval and fee br• 4 parking spaces brbrWake up to breathtaking views from the rooftop deck, spend sunny afternoons splashing in the pool and relaxing in the spa, and gather for dinners by the outdoor grill and covered patio. Siena Sky makes vacation living effortless, with upscale amenities like an elevator, washer and dryer, and upgraded linens to ensure every stay is comfortable and convenient. brbrThe second floor living area is bright and inviting, featuring plush seating, TV, and sliding doors that open to the balcony for seamless indoor-outdoor living. The chef’s kitchen is a highlight with quartz countertops, custom cabinetry, and appliances, while the dining area offers elegant seating for eight. Whether you’re cooking a family feast or enjoying takeout from a nearby restaurant, this open concept space is perfect for gathering together. brbrEach of the four bedrooms is designed as a private retreat, complete with ensuite bathrooms, TVs, and plenty of storage. The primary bedroom boasts a king bed and a spa-inspired bathroom with a standalone tub and walk-in shower, plus balcony access for morning breezes. Two additional king bedrooms provide comfort and style, while the fourth bedroom is perfect for kids with two twin-over-twin bunk beds. With four and a half bathrooms, everyone in your group will enjoy space and privacy. brbrRoom Details br-Primary Bedroom, 3rd floor: King bed, ensuite bathroom with tub and walk-in shower br-Second Bedroom, 2nd floor: King bed, ensuite bathroom br-Third Bedroom, 2nd floor: King bed, ensuite bathroom br-Fourth Bedroom, 3rd floor: Two Twin-over-Twin bunk beds, ensuite bathroom brbrLocated just one minute from the beach and close to Anna Maria’s most popular spots, Siena Sky is perfectly positioned for exploring. Walk to boutique shopping and dining on Pine Avenue, take the trolley to Holmes Beach or Bradenton Beach, or spend the day kayaking, fishing, or booking a sunset cruise. Traveling with a larger group Check out Costa Bella, Siena Sky’s neighboring home, also available for rent. brbrSiena Sky by Anna Maria Island Accommodations is the perfect blend of modern luxury and coastal charm. With a rooftop deck, private pool and spa, and unbeatable location near the Gulf, this home is designed to make your Anna Maria Island getaway unforgettable. Book your stay today and create lasting memories at Siena Sky! brbr- brThis home is managed by Anna Maria Island Accommodations, an Anna Maria Island property management company. Please see our Anna Maria Island Accommodations Rental Policies for full details. brbrWith host approval before check-in, this property accepts dogs only (No cats or other animals are allowed). An additional pet fee will apply. Weight limit of 50lbs max total for 1 or 2 dogs combined. No dangerous breeds allowed. See our Anna Maria Island Accommodations 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. 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.

New Luxury Home with Beach Views and Pool, 1 min to Beach - Siena Sky

Anna Maria, Florida, United States

Bed

Bath

Sleeps

$1011.84

Welcome to Casa Mariposa!brOn Anna Maria Island (Anna Maria, FL)brbrExperience Casa Mariposa — where the rhythm of island life slows, and beauty unfolds in every detail. Just one street north of Pine Avenue and four houses from the beach, this elegant home invites you to wake with the sun, breathe in the salt air, and linger a little longer in the spaces that feel like home.brbrPerfect for: families, couples traveling together, and small groups seeking quiet comfort, style, and connection.brbrHighlightsbr- Single-family home near Pine Avenue and Gulf beachesbr- 4 Bedrooms | 4 Full Baths | 1 Jetted Tubbr- Heated 45-foot private lap pool with spabr- Lush tropical gardens and butterfly sanctuarybr- Multiple screened-in porches and lanaisbr- Open-concept living and dining with seating for 8br- Fully equipped kitchen with coffee bar and breakfast seatingbr- Bonus game area, wet bar, and outdoor cabanabr- Driveway parking for 2 vehiclesbrbrInterior SpacesbrStep through the 100-year-old teak gate, framed by lush greenery, and enter a home designed with care and character. Inside, soft light filters through large windows, reflecting off natural textures and warm wood tones.brbrThe main living area feels both refined and relaxed, with high ceilings and open sightlines that invite connection. Comfortable seating surrounds a Smart TV — ideal for quiet mornings or evenings shared over conversation.brbrEvery detail tells a story: antique teak columns, handcrafted finishes, and art that honors the home's namesake — Mariposa, the butterfly — a symbol of transformation and grace.brbrLayout Overviewbr- Ground Floor: Twin XL bedroom with bonus game area and en-suite bath; King primary suite with walk-in shower and double vanity; second King suite with private screened patio and en-suite bath; hallway wet bar and beverage fridge.br- Main Floor (Second Level): Open kitchen, dining, and living area; King bedroom with workspace; full bath with jetted tub and shower; screened-in balcony overlooking tropical gardens.br- Outdoor Level: Heated lap pool with spa, outdoor shower, cabana, and butterfly garden.brbrOutdoor LivingbrCasa Mariposa's outdoor spaces are where time seems to stretch and soften. Step into a lush tropical oasis where palms sway gently, butterflies drift by, and sunlight dances across the water.brbrThe 45-foot heated lap pool invites early morning swims or late-afternoon floats. A bubbling spa adds a touch of warmth to cool evenings, while the cabana and lounge area offer shade for midday relaxation.brbrEnjoy outdoor dining beneath the palms, or sip your morning coffee surrounded by the soft flutter of wings in the butterfly garden. Every inch of the yard feels intentional — a tranquil retreat designed to restore and inspire.brbrPool & Outdoor Highlightsbr- Heated 45-foot lap pool with spa (82–85°F; weather dependent)br- Outdoor dining area and lounge seatingbr- Poolside cabana and grillbr- Outdoor showerbr- Lush tropical landscaping and butterfly gardenbrbrKitchen & DiningbrThe kitchen is both functional and artful — a space where form meets purpose. Australian serpentine countertops, solid maple cabinetry, and stainless-steel appliances reflect craftsmanship and care.brbrWhether you're preparing a simple breakfast or a family dinner, this kitchen makes cooking feel effortless.brbr- Gas stove, oven, and dishwasherbr- Refrigerator with ice maker and water dispenserbr- Microwave, blender, and toasterbr- Keurig coffeemaker, wine cooler, and dedicated coffee barbr- Breakfast bar seating for 4 and dining table for 8brbrEnjoy meals in the open dining area or step onto the screened balcony to dine in the fresh island breeze.brbrBedrooms & Bathsbr- Each bedroom offers a private, peaceful retreat with thoughtful design and comfort in mind.br- Ground-Level Primary King Suite: En-suite bath with walk-in shower, double vanity, and walk-in closet.br- Second King Suite: En-suite bath, private screened patio, and pool access.br- Twin XL Bedroom: En-suite bath and bonus game area — perfect for kids or relaxed downtime.br- Main-Level King Bedroom: Adjacent to full bath with jetted tub and shower, plus workspace for remote work or creative moments.br- All rooms feature Smart TVs, plush linens, and natural light filtered through soft curtains.brbrAdditional Amenitiesbr- Air conditioning and heatbr- Wireless internet and cable TVbr- Washer and dryerbr- Professionally laundered linens and towelsbr- Hair dryer, iron, and ironing boardbr- Beach towels providedbr- Beach gear rental credit (chairs, umbrellas, carts — details after booking)brbrParkingbr- Driveway parking for 2 vehiclesbrbrCasa Mariposa was designed for those who appreciate balance — between nature and design, energy and ease. Here, mornings begin with birdsong, afternoons drift by the pool, and evenings end with laughter beneath the stars.brbrLocated just steps from Pine Avenue's shops and cafés and moments from the sugar-white sands of the Gulf, it's a home that lets you experience Anna Maria Island at its most graceful.brbrWrite Your Vacation Story here, where each moment feels like a gentle reminder to slow down, breathe deeply, and simply be.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. NO PETS.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: VR18-000146brMax Occupancy: 8 Guests | Max Vehicles: 2brInformation deemed reliable but not guaranteed; subject to change or withdrawal without notice.

Casa Mariposa – AMI Luxury Retreat Steps to Beach & Pine Ave w/ Pool & Spa

Anna Maria, Florida, United States

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