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Holiday rentals with a pool in Bradenton Beach

Find and book unique homes with a pool on Airbnb

Top-rated rentals with a pool in Bradenton Beach

Guests agree: these homes with a pool are highly rated for location, cleanliness and more.

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Home

4.87 out of 5 average rating, 103 reviews

New Golf cart + 4bd/3b w pool/2100 sq ft home

Urban Oasis is a privately owned 2100 sq ft 4 bd, 3 bth on Anna Maria Island. 4 minute walk on a quiet residential street to walk to the beach.This home features grey blue hues, coastal furniture, driftwood accents, themed rooms and designer accents. A brand new 2024 6 str golf cart is included in your rental as well as a premium linen service including all towels and linens. Urban Oasis is truly a turnkey Vacation Rental! We also have a second property, Urban Oasis Too, if you like our style!

Guest favourite

Apartment

4.98 out of 5 average rating, 115 reviews

NEW listing on AMI! Walk to fabulous beach front!

Updated, well appointed, clean and comfortable, my unit at Sandy Pointe II is in a secluded setting just a few minutes walk to a less crowded, quieter section of beautiful AMI beach. From here the Island is at your fingertips! Sink your toes into beautiful white sand, watch gorgeous sunrise and sunsets, enjoy the island vibe and music at our many restaurants! A FREE Island trolly stop is steps from our entrance with grocery, drug store, beach shops and so much more just across E Bay Dr.

Guest favourite

Apartment

4.99 out of 5 average rating, 112 reviews

Silver Sands - Winter Availability!

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!

Guest favourite

Apartment

4.87 out of 5 average rating, 114 reviews

Charming and Updated 1 Bedroom in Runaway Bay

Our charming 1 BR/ 1 Bath condo is a new to the rental market. It was formerly owner occupied. The property is in the Bradenton Beach area of Anna Maria Island. Beach is right across the street with deeded access. The pool is the largest heated pool on the island. Fitness center has newer equipment. There is a fishing pier which also works as a great way to enjoy beautiful views of the Anna Maria sound. Free trolley stop is right in front of the property. Washer/dryer in unit.

Guest favourite

Home

4.97 out of 5 average rating, 159 reviews

BACK Jan 1! Newly Renovated! STEPS 2 Private Beach

NEW Pics Coming! 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.

Guest favourite

Apartment

4.95 out of 5 average rating, 120 reviews

Cozy 2 bed/2.5 bath townhome

Renovated 2 bedroom/2.5 bathroom townhome nestled in a quiet, gated community in Bradenton between I-75 & some of the best beaches in the country. My townhome is 2 bedrooms (queen size) with en suite bathrooms. The beds are queen-sized. Amenities in the neighborhood include large heated pool, tennis and basketball courts, a playground, a volleyball area, a sports field, and a designated parking spot only steps away from the front door. Non-numbered guest parking is also available

Guest favourite

Home

4.99 out of 5 average rating, 102 reviews

1 block to Beach on Pine Ave! Private Pool Oasis

Sat-Sat rentals, usually... Our 3 bedroom, 2 bath townhouse, with a private heated-pool oasis, is on Pine Ave in the heart of Anna Maria - 1 ½ blocks from the best white sand beach on the island - 3 blocks in the other direction to the bay - from sunrise at the City Pier to Sunset on the Gulf of Mexico. Walk or ride a bike to all the quaint stores, shopping and restaurants (plus the local doughnut, taco shop and Northshore Cafe next door) without ever getting in your car!

Guest favourite

Home

4.91 out of 5 average rating, 350 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.

Guest favourite

Apartment

4.93 out of 5 average rating, 117 reviews

Beach Escape & Pool, steps to Beach & restaurants

One block from beautiful beach and waterfront dining. Villa #1 in quaint condo building close to everything Anna Maria Island has to offer. Pickleball court across the street. Pool literally out your back door. Perfect for a small family or a romantic getaway. 2 minute walk to beach, trendy Bridge Street shops, marina & waterfront restaurants, bars. Updated, well-appointed kitchen has everything you need. Beach supplies in condo.

Guest favourite

Guest suite

5 out of 5 average rating, 216 reviews

Off Anna Maria Island ~10min to beach w/salt pool

Stay close to the beach and like a local at Off Anna Maria, a cozy, private guest suite attached to our home with separate entrance, saltwater pool, and shaded outdoor patio. Located ~10 mins from Anna Maria Island, 45 mins from Siesta Key, 1 hr from Tampa in a quiet suburban neighborhood. Your interior space is completely separate from ours. The pool and patio are shared with us. *Travel time estimates depend on traffic.

Guest favourite

Cottage

4.96 out of 5 average rating, 224 reviews

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.

Apartment

4.93 out of 5 average rating, 122 reviews

Beach, Bay & Pool

Steps from the beach, heated pool & right on the water. Spacious 2 bedroom 2 bath with a lovely waterfront balcony. 3 minute walk to a gorgeous white sand beach. Restaurants and shops in walking distance at this IDEAL LOCATION !! Spend hours watching the pelicans & dolphins, it's a wildlife lovers paradise.

Holiday rentals for every style

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Luxurious estates for the ultimate escape

Popular amenities for Bradenton Beach rentals with a pool

Free parking on premises

Air conditioning

House rentals with a pool

Guest favourite

Home

4.93 out of 5 average rating, 117 reviews

Outdoor Oasis,Near AMI & IMG,Htd Pool,Stream,Grill

Guest favourite

Home

5 out of 5 average rating, 23 reviews

Sunkissed & Salty: Guest Favorite! Prime Island L

Guest favourite

Home

4.97 out of 5 average rating, 128 reviews

Twin Palms: Big House Steps to Beach w/Lush Pool

Guest favourite

Home

4.98 out of 5 average rating, 44 reviews

Ready to Host! Anna Maria Chateau. Private Pool!

Guest favourite

Home

5 out of 5 average rating, 118 reviews

HTDPool~2KingSuites~3BathRm~FIREpit~Airhockey~CRIB

Home

5 out of 5 average rating, 10 reviews

Tropical AMI Retreat w/golf cart and POOL

Guest favourite

Home

4.97 out of 5 average rating, 36 reviews

Near AMI-Fire Pit-Hot Tub-Game Room-Putting Green

Guest favourite

Home

4.97 out of 5 average rating, 119 reviews

Near downtown! Saltwater Pool! HOT TUB! Games!

Apartment rentals with a pool

Guest favourite

Apartment

4.93 out of 5 average rating, 369 reviews

Beach Condo, Heated Pool, 2 Minute Walk to Ocean

Guest favourite

Apartment

4.87 out of 5 average rating, 113 reviews

Steps from the beach

Guest favourite

Apartment

4.96 out of 5 average rating, 296 reviews

WE ARE OPEN—On the Beach; Siesta Key SunBum Studio

Guest favourite

Apartment

4.89 out of 5 average rating, 240 reviews

Sunset Beach Condo in Treasure Island

Guest favourite

Apartment

4.99 out of 5 average rating, 108 reviews

Tropical Beachfront Penthouse-Beach Cottages II

Guest favourite

Apartment

4.88 out of 5 average rating, 130 reviews

Royal Orleans at Redington Beach ( Studio 203 )

Guest favourite

Apartment

4.85 out of 5 average rating, 143 reviews

Anna Maria Island-just a few steps to the beach

Guest favourite

Apartment

4.95 out of 5 average rating, 149 reviews

The Seashell Cottage with peaceful water views!

Quick stats about holiday rentals with a pool in Bradenton Beach

Total rentals
680 properties
Nightly prices starting at
€ 66 before taxes and fees
Total number of reviews
8.2K reviews
Family-friendly rentals
540 properties are a good fit for families
Pet-friendly rentals
160 properties allow pets
Rentals with dedicated workspaces
260 properties have a dedicated workspace

Destinations to explore