Family-friendly rentals near Anna Maria Island

A serene outdoor space showcases a sparkling pool framed by lush tropical landscaping. Palms and vibrant plants surround the area, with a flamingo statue in the foreground. Soft lighting from string lights enhances the tranquil atmosphere as the sky transitions to dusk.

5 out of 5 average rating, 54 reviews

Flamingo Royale — Beach Luxury Resort

Welcome to the Flamingo Royale — Your luxury sanctuary! This exquisite escape gives tropical elegance perfect for indulgent relaxation and unforgettable memories. Experience the charm of old Florida with a modern twist in a stylish setting. Step outside to your personal paradise—a shimmering pool surrounded by lush landscaping & palms galore. W/ beautiful Anna Maria Island just moments away, relish pristine beaches, boutique shopping, and fine dining. Experience paradise at the Flamingo Royale!

A private heated pool is surrounded by tropical landscaping and palm trees, creating a serene outdoor space. Two lounge chairs are positioned beside the pool, and a small table is visible on the lawn. Bright sunlight casts a warm glow over the vibrant plants.

4.95 out of 5 average rating, 113 reviews

Breezy Harbor AMI pool retreat near the Beach

Charming Breezy Harbor sits in a quaint, exclusive corner of AMI and boasts a private heated pool and ample parking for 2 vehicles and even a boat: -We typically have shorter stays available, just ask! -If you don't have a single 50Lb pet, please discuss it with us -One of the twin boutique MyAnnaMariaStay homes, look us up! You'll love the luxury mid-century feel, lush yard, and a 6-min walk to the beach, Publix or the trolley stop. AMI was voted a top 50 vacation spot in the world in 2024

A cozy outdoor seating area features two blue chairs positioned near a glass-top table with a glowing fire feature. The background showcases serene water views, surrounded by palm trees and residential homes, under a colorful sunset sky.

5 out of 5 average rating, 40 reviews

Heated Pool, Elevator, Dock, Waterfront, Fire Pit

Escape to The Blue Ark, a unique 3-story home inspired by Noah’s Ark. Families will love this peaceful retreat, blending luxury and comfort. Discover the island's only natural lagoon, boasting stunning views, manatee and occasional dolphin sightings! Unwind by the private pool&spa, fish from the dock, or take an easy 4-5 minute walk to the beach. End the day with a drink by the fire pit on the top deck, watching the sunset. The Blue Ark has an elevator, 3 bedrooms, 8 beds and 4.5 bathrooms.

4.94 out of 5 average rating, 118 reviews

The Peachy Beach House, steps to the gulf

The perfect place for a combination family vacation and some romance-when the kids are in bed, turn on spa and the music. June, July and August, Saturday to Saturday only. If custom trip length is wanted- ask Two bedroom, 2 full bathroom, new heated private pool/spa Steps to semi-private gulf beach, on quiet street in N. HB Well-stocked kitchen, 2 TVs, large primary suite and amazing gulf views from bedrooms. Crib, high chair, beach chairs, wagon, umbrella, beach toys and towels

4.97 out of 5 average rating, 180 reviews

A heated saltwater pool is surrounded by lush tropical vegetation, creating a serene atmosphere. Poolside seating is offered by several lounge chairs, alongside a shaded area with an umbrella. Sunlight reflects off the water's surface, enhancing the tranquil setting.

Home in Bradenton Beach

STEPs to BEACH! /Heated Salt Pool/Sunsets/5 STAR!

Less than a 2 min WALK to the white sand beaches of the Gulf, this 4 BR home comfortably sleeps 8. Large bedrooms & a spacious floor plan (the kitchen, dining and living rooms flow together), the house is perfect for families. The bedrooms are split 2+2 & paired with bathrooms on opposite ends of the house (a pocket door adds privacy). Private heated saltwater pool sits amidst the tropical yard. Hop on the free trolley and explore Florida's gorgeous Anna Maria Island.

Townhouse in Holmes Beach

An aerial view captures the coastal neighborhood, showcasing a collection of charming homes with grey rooftops. The vibrant blue ocean and sandy beach are visible in the background, while lush palm trees surround the area, contributing to the serene island atmosphere.

4.99 out of 5 average rating, 149 reviews

Heated Pool & Spacious Lanai! Steps from Beach!

Welcome to Your Dream Beach Escape! Just one block from the sugar-white sands of Holmes Beach, this newly renovated home has everything you need for the perfect getaway. Bikes, paddle boards, and all the beach gear are included for endless fun! Unwind in the shared HEATED pool or soak up the charm of Anna Maria Island. Shopping, dining, and tropical attractions are just a stroll, bike, or trolley ride away. Perfect for families, snowbirds, reunions, and couples!

A serene outdoor space features a sparkling pool surrounded by lush greenery and tropical plants. Comfortable lounge chairs are placed along the poolside, and string lights cast a warm glow overhead. A shaded seating area with a gazebo can be seen in the background.

4.91 out of 5 average rating, 392 reviews

Palm Retreat: #1 Top Rated Rental of Bradenton/AMI

Enjoy Florida sun in a stunning, newly renovated 4/2 pool home! We have provided almost everything we could think of including five 4k TVs w/ Netflix and cable, wifi, heated (optional) salt water pool w/ 7' privacy fencing, adult bikes, beach gear, Pack & Play, office, board games, relaxing lounge chairs, stocked kitchen, washer & dryer, garage parking, dog crate, all in a quiet and safe neighborhood. Oh, and of course it's just 5 miles to world renowned beaches.

Apartment in Longboat Key

4.98 out of 5 average rating, 216 reviews

Oceanfront Mid-Island on LBK: Open SA-TU, $215/nt!

This sublime oceanfront studio is directly on the pristine white sands and serene blue waters of the Gulf of Mexico in exclusive Longboat Key, Florida! Located on the second floor, overlooking the heated pool and ocean, this dreamy studio condo is optimal for sunset viewing from a private lanai. Take a 30-second walk to the pool and onward to the secluded beach with loungers. Enjoy a relaxing vacation at our peaceful condo at The Beach at Longboat Key Resort!

4.98 out of 5 average rating, 191 reviews

A fire table is positioned near large glass windows that frame a stunning sunset over the water. The reflection of the vibrant sunset is visible in the water, while the outdoor landscape is softly illuminated by the fading light.

Apartment in Bradenton

Luxury 3/3 Margaritaville Resort

Our luxury 3 BR/ 3 Bath Margaritaville inspired condo features one of the best unobstructed water views of Anna Maria Sound and Tampa Bay in the community. The unit features a gourmet kitchen, high-end mattresses, furniture and electronics. The unit comes with bikes and plenty of beach gear. Come enjoy one of the best units in the only luxury development in the area. Skip the hassle of a trip to the off-site management office with keyless entry.

An aerial view captures a serene private pool encompassed by a stone patio, with several lounge chairs arranged nearby. Lush greenery and tropical plants border the scene, while a dark pond reflects the surrounding nature, enhancing a tranquil outdoor space.

5 out of 5 average rating, 116 reviews

Relaxing 3BR Retreat+ Hot Tub + Pool +Beaches +IMG

🌴Welcome to Beachway Haven! This 5-Star ⭐️ hideaway is just mins from Anna Maria Island's Pristine Beaches & the Gulf of Mexico. Dive into relaxation with your own Heated Saltwater Pool & Spa Hot Tub, nestled in a tropical oasis. Only a skip away from Golf Courses, Nature Parks, IMG Academy, & Palma Sola Causeway's Beach Access – your gateway to Horseback Riding, Kayaking, & endless sandy adventures. Shopping & dining are only a few mins away too!

A bright kitchen is showcased, featuring modern cabinetry and appliances. A small dining area with two wooden stools is positioned next to a white countertop. Natural light fills the space through a nearby door and window, creating an open atmosphere.

4.99 out of 5 average rating, 115 reviews

Tranquility on the bay.

Tucked away from the hustle and bustle, my mobile home is located in a very unique neighborhood right on the bay with a little beach 2 min. down the road from my house, where you can sit and enjoy the views or fish. The homes are a combination of mobile homes like mine and houses with the most wonderful people of all walks of life. Very quiet, very safe and friendly. 5 min. to Bradenton beach and 10 min. to AMI.

4.96 out of 5 average rating, 161 reviews

A spacious pool area is surrounded by palm trees and tropical landscaping. The clear blue water of the pool reflects the bright sky. Comfortable lounge chairs are positioned on the pool deck, inviting relaxation. A dining table is visible in the background, shaded by trees.

Flat in Holmes Beach

Cabin 1 at Spinnakers Vacation Cottages

My place is close to the beach, family-friendly activities and the free AMI trolley. You’ll love my place because of the location and the ambiance. Cabin 1 is part of Spinnakers Vacation Cottages located just steps to the sparkling Gulf. My place is good for couples, solo adventurers, families (with kids), and furry friends (dogs, for a small pet fee) Spa maintains same temperature as pool.

Popular amenities for family-friendly rentals near Anna Maria Island

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Family-friendly home rentals with a hot tub

4.96 out of 5 average rating, 259 reviews

A private outdoor space featuring a heated pool and spa, surrounded by palm trees and lounge chairs. The vibrant blue cottage is visible in the background, complemented by carefully arranged landscaping. A pathway of stepping stones leads toward the entrance of the cottage.

Cottage in Anna Maria

Turtle Cottage - Anna Maria Island

A comfortable living area is furnished with a gray sofa and decorative pillows. A large beanbag sits on the textured rug, while a medium-sized TV is positioned on a light-colored console. Natural light fills the space through sliding glass doors, adorned with sheer curtains.

4.96 out of 5 average rating, 113 reviews

Waterfront View Mins To AMI Beaches

A spacious backyard oasis is captured, featuring a private heated pool and spa surrounded by lush greenery. Lounge chairs are positioned nearby, and a hammock hangs between palm trees. An umbrella provides shade over a seating area, creating a serene environment for relaxation.

4.9 out of 5 average rating, 21 reviews

Out of Office by Beach Boutique Rentals

5 out of 5 average rating, 58 reviews

A cozy sleeping area is presented with a spacious bed featuring soft bedding. Custom-built booths with plush green cushions are positioned along large windows, allowing ample natural light. The warm wood ceiling complements the wooden cabinetry, enhancing the overall serene ambiance.

Tiny home in Bradenton

Romantic Quiet Luxury Tiny Home W/ Private Hot Tub

An outdoor dining area is set up with colorful tableware and a pineapple centerpiece. A spacious table with seating for eight is positioned near the saltwater pool, surrounded by lounge chairs and umbrellas. A vibrant playhouse adds a whimsical touch to the lush backyard.

5 out of 5 average rating, 21 reviews

Poppi Beach House: Heated Pool~Mini Golf~Game Room

4.97 out of 5 average rating, 117 reviews

A screened lanai offers a peaceful retreat with a view of the pond and trees reflecting on the water. Comfortable seating is provided, accompanied by a small table. Natural light flows in, enhancing the serene atmosphere of the space.

Apartment in Bradenton

A&A's Paradise near IMG & Anna Maria beaches

Apartment in Bradenton Beach

A spacious living area features a blue sofa and striped armchair, complemented by a wooden coffee table. Large windows allow natural light to illuminate the room, showcasing views of the turquoise Gulf. Light-colored cabinetry and decorative shelving enhance the inviting atmosphere.

4.99 out of 5 average rating, 155 reviews

★Right on the beach ★ Relax and Enjoy ♥ Sunsets!

A comfortable living area features a sectional sofa and a coffee table on a patterned rug. A large flat-screen television is mounted on a wood-accented wall. Natural light filters through sheer curtains, and a decorative plant adds a touch of greenery to the space.

4.98 out of 5 average rating, 117 reviews

Beach House with jacuzzi near AnnaMariaIsland

Family- and pet-friendly home rentals

An aerial view of the outdoor space reveals a heated saltwater pool shaped like a lagoon, surrounded by lounge chairs and umbrellas. A full-size pickleball court takes center stage, complemented by a nearby mini-golf putting green and a trampoline, all set within lush landscaping.

4.9 out of 5 average rating, 20 reviews

New! Luxurious Retreat w/ Resort Amenities by AMI!

The view from the open patio showcases a serene pool area surrounded by palm trees. Two lounge chairs are positioned nearby, inviting relaxation. The space is characterized by a bright and airy feel, with natural light flowing in through large glass doors.

4.91 out of 5 average rating, 23 reviews

Beautiful Pool/Spa, Steps to sand, New Golf Cart

A private backyard swimming pool is surrounded by tropical landscaping and six lounge chairs positioned for sunbathing. The pool features clear blue water, with a paved patio area and a white fence providing privacy. Palm trees and decorative plants enhance the inviting outdoor setting.

4.95 out of 5 average rating, 55 reviews

Gone Coastal - private heated pool near AMI/beach

4.78 out of 5 average rating, 267 reviews

Home

Tropical Oasis - Private Pool - Close Beaches

4.99 out of 5 average rating, 77 reviews

A serene backyard pool area is framed by lush palm trees, creating a tropical oasis. A semi-circular seating area under a Tiki umbrella provides a shaded spot next to the pool. Adjacent seating and a grill enhance this inviting outdoor space.

Cottage in Holmes Beach

Poolside Oasis on Anna Maria Island!

4.97 out of 5 average rating, 176 reviews

A sandy path leads through lush greenery towards the beach, framed by overhanging branches. The ocean is visible in the distance, with light reflecting off the water. Shadows create a peaceful atmosphere as the sun casts a warm glow.

Cottage in Indian Shores

Beautiful Beachfront Cottage on the Water

Apartment in Holmes Beach

4.96 out of 5 average rating, 101 reviews

Steps to the beach! Updated Condo at The Terrace

4.96 out of 5 average rating, 26 reviews

King Bed/Pool/Game Room/Fire Pit/Hammock/Near AMI

Family-friendly home rentals with a pool

A charming island home is presented on a landscaped property, featuring a paved driveway with ample space for parking. The elevated structure is accessible by a set of stairs, and palm trees add a tropical touch to the surroundings.

5 out of 5 average rating, 13 reviews

1 block to Pine Ave + Shopping + Beach + Dining!

An aerial view showcases SunSalt Cottage surrounded by lush greenery and palms. The large private saltwater pool is visible, along with the tiki hut and outdoor seating area. The nearby beach and distant ocean can be seen beyond the charming homes of Anna Maria Island.

4.96 out of 5 average rating, 26 reviews

SunSalt Cottage~5 min to Beach, Shops & Food~Pool

A vibrant outdoor space is showcased with a table and chairs under a large umbrella, surrounded by lush greenery. The game room features a pool table and retro arcade games, while cozy seating areas inside invite relaxation. A glimpse of the heated pool is visible in the courtyard.

4.93 out of 5 average rating, 42 reviews

Ultra Clean, Private Pool & Hot Tub, 6mi to beach

An outdoor lounge area is showcased under a wooden ceiling, featuring a heated pool and elegant patio furnishings. A television is mounted on the wall, and a dining set is positioned nearby, with a barbecue grill just outside the lounging space, surrounded by tropical landscaping.

5 out of 5 average rating, 51 reviews

Book Family Tides 7 Nts get 3 FREE~Pool~Beach view

Townhouse in Holmes Beach

A sandy beach extends towards a calm ocean, where turquoise waters meet a clear blue sky. Colorful umbrellas provide shade for beachgoers, who are relaxing on vibrant towels. The shoreline features soft white sand, inviting visitors to enjoy the peaceful environment.

4.92 out of 5 average rating, 49 reviews

Getaway Family Beach Townhome w/Pool!

A large heated saltwater pool is enhanced by colorful floating rings. A waterfall feature adds a calming effect while lounge chairs are positioned nearby. The patio area is visible, furnished with multiple seating options, and surrounded by lush greenery and sunny skies.

5 out of 5 average rating, 61 reviews

NO FEES | Heated Pool | Game Room | Sleeps14 | BBQ

A serene outdoor area features a heated pool surrounded by tropical landscaping. Light-colored pavers outline the pool, and large sliding glass doors lead to an inviting sunroom. Towering palm trees provide shade, contributing to the tranquil ambiance.

5 out of 5 average rating, 72 reviews

Private Luxurious Ground Level Home

4.98 out of 5 average rating, 46 reviews

Loggerhead - Private Pool + Golf Cart - AMI Oasis

Family-friendly home rentals with wifi

An outdoor area features a heated pool surrounded by lounge chairs, a pickleball court, and a putting green, all enhanced by tropical landscaping. The interior reveals a comfortable game room with arcade games and modern amenities, providing a relaxing atmosphere for all guests.

5 out of 5 average rating, 24 reviews

Fall Special! - Family Fun - 9 min to Beach

An aerial view showcases a spacious, heated swimming pool adjacent to a vibrant outdoor recreation area featuring a pickleball court and nearby children's playground equipment. The lush green lawn is neatly bordered by privacy fencing, enhancing the inviting atmosphere for recreation and relaxation.

5 out of 5 average rating, 51 reviews

Pickleball, Axe Throwing, Mini-Golf, Bowling, IMG

The heated saltwater pool is viewed at night, with tranquil blue water reflecting the overhead lights. An outdoor kitchen and seating area are visible in the background, featuring a movie screen, bar seating, and dining tables, all wrapped in string lights for a cozy ambiance.

5 out of 5 average rating, 73 reviews

Close to IMG + Pool + Outdoor Kitchen & Projector!

A private heated pool, approximately 33 feet long, is surrounded by lush greenery. Covered in-pool seating and a small table are visible, along with a patio area featuring an outdoor shower and an umbrella-shaded dining table for six.

4.83 out of 5 average rating, 6 reviews

Turtle Nest! Private Heated Pool and Access to the

The outdoor area features a private heated pool with a separate spa, surrounded by lush gardens and palm trees. Comfortable lounge chairs are positioned along the poolside, and a grill area is visible, creating a serene and inviting space for relaxation.

4.97 out of 5 average rating, 33 reviews

Casa Mariposa – AMI Retreat w/ Pool, Spa & Beach

5 out of 5 average rating, 6 reviews

Flat in Bradenton Beach

Beachfront Studio Retreat on Anna Maria Island

Apartment in Holmes Beach

A bright living space features light blue walls and natural light streaming through large windows. Two white chairs with starfish cushions are positioned facing a small table. The decor includes small lamps and a decorative sign on the wall, enhancing the coastal ambiance.

4.95 out of 5 average rating, 82 reviews

Island Beach Paradise, Close to Everything, Bikes

The open-concept living area features a modern dining table set with intricate lace placemats. A pink sofa and white chairs provide ample seating, complemented by a stylish chandelier overhead. Bright natural light fills the space, highlighting decorative plants and framed artwork.