Family-friendly rentals near Anna Maria Island

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

4.99 out of 5 average rating, 239 reviews

A private stock tank pool is surrounded by a wooden deck and lounge chairs. An umbrella provides shade over the pool area. Colorful towels and a stylish table with refreshments are visible, set amidst a landscaped courtyard with lush greenery.

Guest house in Sarasota

Magical Guesthouse 1 mi from SRQ airport

@Aloe_Stranger Dreamy + fresh! This 1-bedroom guesthouse has a king bed, full bath, kitchen, washer/dryer, daybed + sleeper sofa. NEW STOCK TANK POOL! Full of style - it feels like you're in your own art installation. 1 mile from SRQ Airport, it boasts a great location as well cushy comforts. 1/2 mile from Sarasota Bay, 15 min from Lido Beach, 15 min from Siesta Key and many beaches around the Sarasota/Bradenton area. 10 min from downtown Sarasota, 1 mile from the historic Ringling Museum

Apartment in Longboat Key

4.99 out of 5 average rating, 163 reviews

Beach Condo Open Tomm $100/nt+Fees!

This charming seaside condo 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 one-bedroom condo is optimal for sunset viewing from a private, screened lanai. Take a 30-second walk to the pool and onward to the secluded beach with loungers and sun umbrellas. Enjoy a relaxing vacation at our peaceful condo at Silver Sands Gulf Beach Resort!

4.97 out of 5 average rating, 121 reviews

The bedroom features a spacious bed with decorative pillows and a light blue throw. An accent bench sits at the foot of the bed, while a round mirror reflects soft lighting from a chandelier. A patterned wallpaper adds a coastal touch, enhancing the serene ambiance.

Apartment in Bradenton

KING Bed + Anna Maria Island Beaches + Beach Gear!

⚓️🦩Welcome to the Coastal Flamingo! Your nautical getaway that combines style, fun, and the serene beauty of the Gulf Coast. This cozy, vibrant themed condo is the perfect destination for your next Beach vacation. Walking distance to Palma Sola Beach Causeway, where you can enjoy sun-bathing, horseback riding, jet skiing, and fishing! 5 mins or less from the Gulf of Mexico and powdery white sand beaches of Anna Maria Island! Kick back and relax in this coastal escape!

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 three-story coastal home is framed by palm trees, featuring a light-colored exterior. A large balcony is visible on the second floor, and the entrance includes a garage and a fenced area. The setting is serene, highlighting the proximity to the beach.

4.94 out of 5 average rating, 117 reviews

The Peachy Beach House, steps to the gulf

For June, July and August, Saturday to Saturday stays only. If custom trip length is desired, please send inquiry. Two bedroom, 2 full bathroom, new heated private pool Steps from semi-private gulf beach, this 3 story on a quiet street in N. HB Well-stocked kitchen, 2 TVs, large master which is more like resort suite with new tempurpedic king bed Gulf views from bedrooms. You’ll find: crib, high chair, beach chairs, wagon, canopy, beach toys and towels!

Guest house in Bradenton Beach

A vibrant yellow cottage is depicted with a landscaped area featuring palm trees and a gravel yard. Colorful adirondack chairs in pastel shades of pink and blue offer seating options, creating a casual outdoor space. Nearby cottages are visible, enhancing the beachfront setting.

4.99 out of 5 average rating, 194 reviews

Bradenton Beach Sunsets 1, Anna Maria Island, FL

Fully furnished water view beach cottage located on beautiful Anna Maria Island directly across the street from white sand beach and Gulf of Mexico. 1 Bedroom 1 bath unit that sleeps 4 with the queen pull out couch. Beach chairs/umbrellas/Boogie boards/laundry room, etc. provided. Three blocks from historic Bridge Street with lively restaurants and bars. Free island trolley and across the bridge from Cortez fishing village. Free off-street parking.

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, 115 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!

4.97 out of 5 average rating, 258 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

Great 1 bedroom, 1 bathroom cottage on the quiet north end of the island. The house is conveniently located and within walking distance (two short blocks) to the beach and close to the intersection of Gladiolus Street/Alamanda Road. Spectacular sunrises are just a short walk away at the Rod and Reel Pier, and the sunsets at Bean Point Beach are second to none, just a few blocks away. This great getaway sleeps up to 4.

4.94 out of 5 average rating, 115 reviews

A spacious bed with a soft headboard is centered against a light-colored wall. Two pillows are arranged neatly on the bed, complemented by a cozy blanket. A bedside table holds a lamp and a small plant, while wall-mounted shelves display additional greenery.

Guest house in Bradenton

Peaceful Paradise

Kick back and relax in this calm, stylish space. Our one bedroom, one bath guesthouse has a private entrance, and separate fenced area. The neighborhood is safe and quiet. Four miles to IMG (Bradentons premier sport's school) and just 6 miles to the beautiful sandy beaches of Anna Maria Island. A perfect location for professionals, traveling singles and couples looking to get away.

4.97 out of 5 average rating, 341 reviews

A stunning pool area is surrounded by lush greenery and tropical plants. A prominent rock feature with multiple waterfalls is visible, providing a serene focal point in the outdoor space. The vibrant blue water complements the natural elements, creating a tranquil retreat.

Island in Sarasota

*DEC SALE! Sarasota #1 Luxury Villa w/PRIV BEACH!

BOOK 2025 NOW, and stay in Style magazines exclusive beachfront gem! This property OWNS THE BEACH!! UNIQUE PRIVATE POOL & BEACH combo is HEAVEN! Private ELEVATOR! 32,000/gl FREEFORM POOL, with 4 WATERFALLS, HOT GROTTO with HOT falls! NEW BBQ PIT AREA, BIKES, KAYAKS, and PADDLEBOARDS! WRAPAROUND BALCONY, CHEF kitchen. Hosted CELEBS! SHOPPING, FINE DINING, watch our VIDEOS!

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

A spacious bedroom features a large bed with striped bedding, complemented by two nightstands with lamps. Sliding glass doors open to a private backyard with a plunge pool. Natural light floods the room, highlighting the warm wooden ceiling and inviting decor.

4.96 out of 5 average rating, 198 reviews

Sea AMI

4.94 out of 5 average rating, 67 reviews

A coastal-style duplex is framed by lush tropical landscaping, featuring palm trees and colorful flowering plants. The exterior showcases light-hued siding, a spacious front porch with railings, and two garage spaces below. A clear blue sky enhances the inviting atmosphere of the property.

Cottage in Holmes Beach

Close to the Beach+ Private heated pool and spa!

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, 154 reviews

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

4.91 out of 5 average rating, 136 reviews

A fire table is positioned in view of a vibrant sunset, reflecting shades of orange, pink, and purple across the sky. The scene is framed by large glass panels, offering unobstructed views of the horizon, enhancing the outdoor experience.

Apartment in Bradenton

New Luxury 3/3 Condo in Margaritaville Resort

4.97 out of 5 average rating, 106 reviews

A bright living room features a large, light-colored couch adorned with patterned cushions. A swing chair hangs in the corner, and a coffee table sits in front of the couch. Soft lighting and large windows enhance the cozy atmosphere.

Home in Sarasota

Cozy Boho Bungalow Pool/Spa QR Code Walkthrough

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, 116 reviews

Beach House with jacuzzi near AnnaMariaIsland

4.9 out of 5 average rating, 188 reviews

Black Friday Deals NOW -Sunshine, Fun & Holidays

Guest house in Anna Maria

The exterior view of a two-story home is presented, featuring a wooden staircase leading to a balcony adorned with outdoor seating. Lush greenery surrounds the property, with a variety of plants and flowers lining the pathways, creating a welcoming outdoor space.

4.95 out of 5 average rating, 244 reviews

Gulf Front Guest House

Family- and pet-friendly home rentals

The outdoor area showcases a heated saltwater pool enclosed by a screen, with vibrant citrus-themed murals on the walls. Soft lighting from string lights illuminates the space, enhancing the inviting atmosphere during twilight. A spacious sun deck offers seating and relaxation areas.

4.99 out of 5 average rating, 112 reviews

Saltwater heated pool w/ massage chair + hot tub

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 heated pool is surrounded by tropical plants and lounge chairs, providing a serene setting. Soft lighting creates a relaxing atmosphere as evening approaches. A pergola stands nearby, enhancing the outdoor space.

5 out of 5 average rating, 22 reviews

The Toasty Coconut in Anna Maria

A bright dining area features a round glass table surrounded by four white upholstered chairs. A blue circular rug lies beneath the table, and large glass doors provide views of the nearby canal, enhancing the natural light in the space.

5 out of 5 average rating, 5 reviews

Manatee Retreat B

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

Apartment in Holmes Beach

4.96 out of 5 average rating, 99 reviews

Steps to the beach! Updated Condo at The Terrace

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

4.96 out of 5 average rating, 24 reviews

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

Family-friendly home rentals with a pool

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, 25 reviews

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

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, 23 reviews

Fall Special! - Family Fun - 9 min to Beach

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

Elevator, Heated Pool, Dock, Waterfront, Fire Pit

A warm outdoor space features a heated pool surrounded by tropical landscaping. Comfortable black lounge chairs are positioned nearby, providing a relaxing area for guests. Soft lighting illuminates the space, creating a serene atmosphere in the evening.

5 out of 5 average rating, 54 reviews

Perfect Hideaway- Heated Pool, 5 min Walk to Beach

4.98 out of 5 average rating, 46 reviews

Loggerhead - Private Pool + Golf Cart - AMI Oasis

A spacious living area is defined by high ceilings and an open layout, featuring two comfortable sofas facing a wall-mounted television. Large glass doors provide a view of the lush backyard, while decorative plants add a touch of greenery to the room.

4.98 out of 5 average rating, 49 reviews

Unwind Sunshine: steps to locals' favorite beach

4.97 out of 5 average rating, 37 reviews

A cozy bedroom features a spacious bed with light bedding, accented by decorative pillows. Natural light streams through sheer curtains by the window, illuminating the room's soft blue walls. A wooden dresser and a ceiling fan add functional elements to the friendly space.

Villa in Holmes Beach

Starfish House - 2bed/2bad

5 out of 5 average rating, 14 reviews

NO FEES | Oasis | Heated Pool, Hot Tub & Game Room

Family-friendly home rentals with wifi

5 out of 5 average rating, 57 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

5 out of 5 average rating, 9 reviews

Casa Cay by Duncan Real Estate

The backyard features a saltwater pool surrounded by artificial turf, creating a refreshing oasis. Sunlight brightens the outdoor space, accentuated by lush tropical landscaping. The elevated home showcases multiple balconies, while palm trees lend to the coastal atmosphere of the property.

4.94 out of 5 average rating, 16 reviews

Bayfront Beach access with Heated Pool!

Home in Indian Rocks Beach

5 out of 5 average rating, 10 reviews

Waterfront Manatee Home Pool, Dock, Optional Boat

A sparkling blue pool is surrounded by a stone deck and lush greenery. Lounge chairs are positioned beside the pool, with a covered patio in the background. The water canal and boats are visible beyond the backyard, under clear blue skies.

5 out of 5 average rating, 38 reviews

Canal front, dock, heated Pool, near AMI+IMG

4.98 out of 5 average rating, 87 reviews

A spacious bed is centered in the room, dressed in a striped quilt. Two bedside lamps provide soft lighting, while framed artwork and a decorative sign enhance the calming atmosphere. A cozy seating area is positioned nearby, complementing the restful environment.

Guest suite in Bradenton

Sand Dollar Oasis - private entrance, private bath

5 out of 5 average rating, 5 reviews

Flat in Bradenton Beach

Beachfront Studio Retreat on Anna Maria Island

A serene outdoor area features a well-maintained lawn with stone pathways and tropical landscaping. Palm trees provide shade around a bar area, overlooking the water. A private dock is visible in the background, with the gentle bayou waters reflecting the blue sky.