Family-Friendly rentals near Anna Maria Island

4.96 out of 5 average rating, 111 reviews

Condo in Holmes Beach

Steps to the beach! Condo with pool at The Terrace

Just 200 steps from the white sands of Holmes Beach, this beautifully updated 2BR/2BA condo has everything to offer! Our unit features high-speed internet, Keurig , balconies off of each bedroom, 1-car garage, washer/dryer, heated shared pool, and access to all the beach necessities (toys, umbrellas, chairs, tent, bicycles, SUP, cart). This unit sleeps 6 (1-King, 1-Queen, & Full size sofa bed). LOCATION, LOCATION! You'll be just steps from restaurants, cafés, shops, and the free island trolley!

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.

Getaway Family Beach Townhome w/Pool!

Wouldn't you like to get away?🌞 Just steps to the perfect family beach at this condo w/pool. Two bedrooms, two baths (+tub), sleeps six! King bed, queen w/twin bunk over, one convertible queen. Fresh updates: Washer-dryer, flooring, sofa, full kitchen, cable, wifi, beach toys, pack n play, baby gate. Did we mention the heated pool?🏊‍♀️ Next door to Walgreens, restaurants, bike rentals, shops, grocery. So many charming delights to discover on America's best beach, Anna Maria Island (AMI)!🏖

4.94 out of 5 average rating, 72 reviews

4.88 out of 5 average rating, 112 reviews

Condo in Holmes Beach

#terraceLIFE | 2 Blocks to Beach | Heated Pool

Escape to our cozy beachside retreat, steps from the sand! Retire the car in the garage, fill the wagon w/beach supplies & head to the shoreline at sunset. Spend time sipping coffee on 1 of the 3 balconies or cooling off in the pool w/the lush landscape. There's no better way to relax & enjoy AMI! Bedrooms on 2nd floor giving the main level separation. Sleeps 4-5 comfortably but can accommodate 6 w/sofa bed. Forgot something? Walgreens is right next door along with restaurants, shops & more!

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.

Steps from Beach! Heated Pool & Spacious Lanai!

Your Dream Beach Getaway! One block from the sugar-white sands of Holmes Beach, this freshly renovated coastal retreat is ready for your perfect island vacation! Cruise around on our free bikes, paddle our boards, or hit the beach with all the gear you need for a day in the sun. When it’s time to relax, take a dip in the shared, HEATED pool! At night, enjoy the laid-back charm of the Island. Explore local shops, delicious eats, and island vibes—all just a short bike ride from our home. .

4.98 out of 5 average rating, 172 reviews

4.98 out of 5 average rating, 125 reviews

Home in Bradenton Beach

Gulf Front! Sunset Deck! + Walk to Bridge St Pier!

🌊🏄Welcome to The Surof House - where panoramic views of the Gulf of Mexico welcome you from almost every corner! 🏖️Experience the ultimate beachfront retreat at this unique & stunning property nestled across from one of the top beaches in the world. A perfect blend of luxury, comfort, & unparalleled views awaites. With an upstairs loft featuring 3 single beds & 2 downstairs rooms with king beds, it's an ideal getaway for families, friends, or anyone seeking a slice of paradise.

A private heated pool features a waterfall, surrounded by lush tropical landscaping and palm trees. Seating options include teal lounge chairs and white sunbeds, while the pool deck is complemented by a well-maintained lawn area. Colorful plants enhance the tranquil outdoor space.

4.97 out of 5 average rating, 111 reviews

Salty Harbor AMI pool retreat near the Beach

Charming Salty 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: -Ask us if your dates don't fit our calendar! -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 private pool is surrounded by a tropical landscape, featuring palm trees and vibrant plants. The clear water reflects the blue sky, and a spacious deck with paver stones offers a welcoming area for relaxation. A canal can be seen in the background.

4.95 out of 5 average rating, 207 reviews

Sunshine Cottage: 30’ Pool & Dock, Steps to Beach

o A beautifully renovated 3-bed 2-bath oasis designed for unforgettable family getaways, boating adventures, and pure relaxation. o While many rentals claim to be in Anna Maria, they are actually situated in the heavily congested Holmes Beach or Bradenton Beach areas. Nestled on the quiet, historic North End of Anna Maria City. Completely bypass the tourist traffic and long car lines, enjoying a peaceful, authentic neighborhood where everything you want is within a short stroll.

4.84 out of 5 average rating, 207 reviews

Bungalow in Anna Maria

Bay Breeze Cottages #3

Bay 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.

4.9 out of 5 average rating, 238 reviews

A screened lanai offers poolside views, with vibrant orange and blue chairs positioned to enjoy the scenery. Lush greenery borders the area, while palm trees sway in the gentle breeze. Glimpses of the Gulf of Mexico and a heated pool are visible through the railing.

Condo in Longboat Key

Beachfront Resort, Ocean View, Pool, Tennis, Gym

Beachfront on beautiful Longboat Key, this condominium offers all the amenities of a resort with the privacy and seclusion that has Silver Sands Beach Resort guests returning each year. Enjoy a coffee on your private patio looking at the Gulf and the beach. Relax on our private beach, walk on our soft white sand, take a dip in our heated beachside pool, or enjoy complimentary chaise lounges and beach umbrellas while breathing in the fresh air. You can't get closer to the beach.

A private pool is surrounded by tropical landscaping, featuring a clear blue water surface that reflects soft lighting. Several lounge chairs are positioned nearby, providing relaxation space under the palm trees. The serene area is perfect for unwinding after a day at the beach.

4.96 out of 5 average rating, 107 reviews

Beach House w/Private Pool & Spa

Adorable beach cottage on the north end of Anna Maria Island! The beach access trail to the beautiful beach is right by the house. This 3 bedroom 2 bathroom home is situated on a corner lot on a quiet street and is located just steps to the beaches of the Gulf of Mexico. Enjoy the private pool and spa, surrounded by tropical landscaping. Tons of beach gear included! It is located in a great area to explore by bike, ride to Pine Ave., Bayfront Park, the City Pier, etc....

Cottage in Bradenton Beach

A vibrant yellow cottage is surrounded by a sandy area with palm trees. Colorful adirondack chairs in pink, blue, and green are positioned on the white gravel. A covered outdoor seating area is visible to the side, enhancing the beachside environment.

Bradenton Beach Sunsets 2, 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.

4.98 out of 5 average rating, 257 reviews

4.96 out of 5 average rating, 282 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.

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

An outdoor dining area is set with a glass table and six blue chairs, shaded by a blue umbrella. In the background, a swimming pool with surrounding tropical plants invites relaxation, while a spa is visible nearby, offering a serene ambiance.

4.82 out of 5 average rating, 104 reviews

Private pool, only two blocks .3 miles from beach!

4.92 out of 5 average rating, 224 reviews

Home in South Bradenton

Summer Vibes*HTD Pool*Hot Tub*Fire Pit*Game Room

4.96 out of 5 average rating, 212 reviews

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.

Home in Bradenton beach

Sea AMI

4.98 out of 5 average rating, 103 reviews

A well-maintained front yard features lush green grass and a large agave plant. The house, showcasing a contemporary design, is flanked by palm trees. A driveway leads to a two-car garage, with additional landscaped areas adding to the outdoor appeal.

Home in Cortez

Dockside Dreams - Pool, Spa & Waterfront Dock

The entrance showcases a welcoming porch adorned with vibrant tropical plants and flowers. A dark front door is flanked by well-maintained greenery. Soft light illuminates the area, creating an inviting atmosphere at the threshold of the property.

4.8 out of 5 average rating, 107 reviews

Island Oasis on Anna Maria Island off Pine Ave

4.99 out of 5 average rating, 182 reviews

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.

Condo in Bradenton Beach

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

5.0 out of 5 average rating, 102 reviews

Home in Bradenton

Lux Getaway: Pool| Hot Tub| Bocce Ball nr AMI &IMG

4.96 out of 5 average rating, 149 reviews

A spacious patio is highlighted by a heated pool, surrounded by a decorative stone border. Comfortable outdoor seating is arranged nearby, beneath string lights that create a soft glow. A serene water view and lush greenery are visible in the background, enhancing the outdoor ambiance.

Home in Bradenton

Casa Bella-5BR/Waterfront/Pool/Spa-9 Min AMI

Family- and pet-friendly home rentals

Superhost

A winding stone path is bordered by lush greenery, leading through the expansive yard surrounded by tall trees. Various native plants are visible, creating a natural and serene environment.

4.8 out of 5 average rating, 270 reviews

Charming Beach house amongst huge Banyon Trees

The duplex features a light blue exterior with a welcoming porch adorned with yellow and blue chairs. Lush palm trees and vibrant landscaping enhance the outdoor space, while a clear blue sky adds brightness to the scene. Graveled parking is visible in front of the unit.

4.94 out of 5 average rating, 105 reviews

Do you love the beach?

4.91 out of 5 average rating, 426 reviews

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.

Home in Bradenton

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

Superhost

Home in Bradenton Beach

AMI Sunset Beach - Gulf View Retreat w/ Pool+Decks

4.81 out of 5 average rating, 117 reviews

Apartment in Bradenton Beach

Newly Remodeled Beachfront Studio - On the sand!

4.92 out of 5 average rating, 155 reviews

5.0 out of 5 average rating, 11 reviews

NEW! w/ Pool - The Pearl Unit 2 on AMI

5.0 out of 5 average rating, 29 reviews

Walk to Beach + Trolley + Heated Pool + Mini Golf!

4.98 out of 5 average rating, 58 reviews

Golf Cart Included | 3 BR | Beach One Block Away

Family-friendly home rentals with a pool

5.0 out of 5 average rating, 65 reviews

Waterfront, Heated Pool, Elevator, Fire Pit, Dock

A private heated pool is surrounded by lush tropical landscaping and features a stone border. A patio area with outdoor furniture is positioned nearby, while palm trees gently sway in the breeze. The bright blue sky enhances the serene atmosphere of the space.

4.85 out of 5 average rating, 61 reviews

Cozy Cottage - POOL HOME! 3/3

Apartment in Holmes Beach

A coastal view showcases a vibrant poolside area surrounded by lush greenery and palm trees. The inviting blue waters of the ocean are visible in the background, enhancing the outdoor space with a sunny, bright sky.

Beachfront Anna Maria Island, Walk to Shops!

4.95 out of 5 average rating, 41 reviews

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.

4.98 out of 5 average rating, 65 reviews

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

5.0 out of 5 average rating, 14 reviews

Dockside Dream:Luxury canal front home, dock, pool

4.88 out of 5 average rating, 51 reviews

AMI 1 Block 2 Beach, Big Heated Saltwater Pool

4.97 out of 5 average rating, 35 reviews

Manatee Sanctuary - in the heart of Anna Maria

5.0 out of 5 average rating, 5 reviews

Tamatoa - Upscale Three Bedroom!

Family-friendly home rentals with Wifi

Townhouse in Holmes Beach

The exterior of the townhome is shown, featuring a light-colored facade with blue shutters. A welcoming entryway is framed by two trees and tropical plants, with white gravel and a decorative fence in the foreground.

Townhouse 200 Steps to the Beach

5.0 out of 5 average rating, 28 reviews

A two-story beach house features a wooden staircase leading to a wrap-around balcony. Lush tropical landscaping surrounds the entrance, and several palm trees are visible. Large windows allow natural light to fill the home, enhancing the inviting facade.

4.98 out of 5 average rating, 41 reviews

Anna Maria Beach House

Apartment in Bradenton Beach

Beachfront Corner Condo | Sunset Gulf Views

4.98 out of 5 average rating, 55 reviews

4.88 out of 5 average rating, 60 reviews

Apartment in Anna Maria

Anna Maria 2BR Condo • Walk to Beach, Dining, Pier

5.0 out of 5 average rating, 23 reviews

Pergola Oasis | Walk to Beach + Outdoor Living

Superhost

5.0 out of 5 average rating, 5 reviews

NEW! Steps to Beach, Hot Tub, Pool, Kid Friendly

The exterior of the historic home is shown, featuring a wide wrap-around porch adorned with American flags. Several rocking chairs provide seating, surrounded by lush greenery and a gravel pathway leading to the entrance. Sunlight casts a warm glow on the porch area.

4.87 out of 5 average rating, 53 reviews

Welcome to our historic Florida beach HOME

An aerial view showcases a spacious outdoor area featuring a private pool and lounge chairs, surrounded by a gated patio. A light blue house stands in the background with multiple windows, providing a connection between indoor and outdoor spaces. Lush greenery lines the property.