Vacation rentals with a pool in Bradenton Beach

4.96 out of 5 average rating, 113 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!

ValueLocationHospitality

Adirondack chairs in soft blue are positioned on the sandy beach, offering scenic views of the ocean and coastline. The sun reflects off the water, enhancing the tranquil atmosphere, while a distant figure strolls along the shore. Lush greenery borders the sandy area.

4.95 out of 5 average rating, 204 reviews

Beach Escape & Pool, steps to Beach & restaurants

One block from beautiful beach & waterfront dining. Newly renovated Villa in quaint quiet condo building close to everything on Anna Maria Island. Pickleball across the street. Pool literally out your back door. Perfect for a small family or a romantic getaway. *Min. renter age 25. Two minute walk to beach, trendy Bridge Street shops, marina, restaurants, bars, boat tours, mini golf and more. Brand new beds, furniture & appliances. Kitchen has everything you need. Beach supplies in hall closet.

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A spacious living area features a large sectional sofa, offering ample seating. A contemporary chandelier hangs from the ceiling, while a light-colored coffee table sits at the center. In the background, a modern kitchen is visible, accentuated by sleek cabinetry and bright lighting.

4.96 out of 5 average rating, 124 reviews

AMI/IMG/Boat/Bikes/Golf/Hottub/Kayak/Beach/pool

Welcome to the Paradise Fun House, the ultimate spot for your dream bash! Our Airbnb oasis is packed with tons of fun and activities for an epic stay. Cruise around on free bikes or kayaks, fish with top-notch gear, challenge friends to mini-golf, chill in the hot tub, or enjoy our game collection. Golf clubs and beach gear are ready to roll. Our spacious layout is perfect for partying all night long. Book now for the ultimate fun or relaxing experience! Boat/Dog-sitting/cleaning are available

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Townhouse in Bradenton Beach

A refreshing pool is surrounded by lounge chairs and tropical greenery, offering a relaxing outdoor space. The vibrant blue exterior of the condo stands out against the palm trees, while beach access is visible in the background, ensuring proximity to the sandy shores.

The Perfect Beach Escape: Just a 1-Minute Walk!

Immerse yourself in our Gulf Coast paradise. Second floor, 3 BR unit of two unit condo with pool shared between only the two units. The heated pool area is an oasis! Each unit has its own private outdoor seating/grill area. One car garage & 2 car spaces, ideally located 1/2 block to the white sands and azure waters of Bradenton Beach and two blocks to the Bay with access for kayaks, picnic area, playground, basketball court and two new pickleball courts. The beach sunsets are spectacular!

LocationFamilyComfort

4.97 out of 5 average rating, 101 reviews

Bungalow in Bradenton Beach

A tranquil outdoor space features a wooden dining table surrounded by eight chairs set on a tiled patio. A small, curved swimming pool is framed by lush tropical plants, and umbrellas provide shaded areas. The vibrant greenery creates a serene atmosphere.

Bougie Bungalow at the Beach

This newly renovated, completely private, comfortable Anna Maria Island bungalow is super clean & very comfortable. It has an open, split floor plan, 2 king bedrooms, each with private baths, separate dining and Florida room & is only 3 houses from the amazing white sand beach, the bay & Pier. Only 1 block over is Historic Bridge Street with cool restaurants, mini golf, quaint shops & bars with live music. Once here, you never need to drive -everything is within a block walking distance!

LocationValueSleep quality

4.91 out of 5 average rating, 128 reviews

A two-story yellow condo is highlighted against a clear blue sky. Palm trees line the pathway leading to a fenced pool area. The entrance features a covered balcony with white railings, offering a welcoming view of the surrounding tropical landscape.

4.92 out of 5 average rating, 129 reviews

Beachy Chic! 1st Floor Condo-Pool-Close to Beach

Enjoy this NEWLY RENOVATED FIRST FLOOR 2-bedroom 1 bath condo just a short easy 2-minute walk to the BEACH. The New Key West vibe includes a Custom White Kitchen w/ SS appl, Shiplap, luxury plank flooring, & W/D combo. The pretty modern bath was updated with custom quartz top vanity. Relax at the pool directly next door & enjoy morning coffee on the little covered patio. The 2nd bedroom can be made up as 2 twins or a King. Walk to wonderful restaurants & shops. Gas Golf Carts permitted.

LocationFamilyNearby

4.97 out of 5 average rating, 113 reviews

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.

Home in Holmes Beach

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

FamilyValueKitchen

4.76 out of 5 average rating, 152 reviews

1 bedroom condo, only 200 steps from the sand !

Enjoy beautiful Bradenton Beach in our newly refurnished vacation rental. We invite you to lounge by our crystal blue pool, swim in the calm gulf waters, or walk along AMI's sugar sand beaches. 2 guests are ideal in our 1 bedroom apartment. We have a double height 24 inch queen air mattress to accomodate up to 2 additional guests. The kitchen is fully equipped and features full sized fridge, stove, oven & coffee maker. The unit has high speed wifi, smartTV, Netflix, cable, & DVD.

LocationValueKitchen

A modern, two-story house features a light blue exterior and is surrounded by palm trees and lush landscaping. A paved driveway leads to the welcoming entrance, flanked by steps that provide access to the outdoor balcony areas. The home is set against a clear sky.

4.88 out of 5 average rating, 100 reviews

Spectacular Beach/Bay views private pool elevator

TWO MASTER SUITES! Modern home within walking distance to Beach, Bay, Historic Bridge Street, pier, restaurants, shops, ice cream, mini golf, fishing, water sports, this location has it all! You will absolutely love the convenience here! Enjoy our beautiful beaches, watch sunsets and sunrises from your balconies or enjoying the heated pool. We are the second house from the beach 50 yards and your toes will be in the sand. Clean quiet street but close enough to walk anywhere.

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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.

4.98 out of 5 average rating, 206 reviews

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.

LocationFamilyBackyard

4.97 out of 5 average rating, 213 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.

Condo 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.

LocationFamilySleep quality

4.94 out of 5 average rating, 107 reviews

Home in South Bradenton

Stylish Pool Home • Near IMG & Beaches • Top Rated

Just 2.2 miles from IMG Academy and 6.5 miles from Sarasota Airport! Near beautiful Coquina and Anna Maria beaches. Enjoy a private pool, ping pong table, and modern comforts in this stylish 3-bedroom, 2-bath home. Fully equipped kitchen, washer/dryer, smart TV, and fast Wi-Fi. One pet allowed with a $200 fee. Relax or entertain in the spacious fenced backyard. Ideal for families or couples seeking comfort, sun, and fun in Bradenton!

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Popular amenities for Bradenton Beach rentals with a pool

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

House rentals with a 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.

4.99 out of 5 average rating, 104 reviews

Heated Pool | Game Room | Arcade | Sleeps14 | BBQ

LocationFamilyQuiet

A saltwater heated pool is surrounded by a spacious patio area. Two lounge chairs with striped cushions are positioned nearby, along with a shaded bar area. Lush palm trees provide a tropical feel, with a well-maintained lawn and a privacy fence visible in the background.

4.94 out of 5 average rating, 246 reviews

Private Heated Pool, Turfed Putting Green Retreat

ValueFamilyParking

4.97 out of 5 average rating, 129 reviews

The Orange Oasis-Private Heated Pool, Near Beaches

FamilyLocationCleanliness

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.

4.96 out of 5 average rating, 155 reviews

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

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An inviting exterior view of Sunrise Villa showcases a well-maintained landscape featuring lush greenery and vibrant plants. A spacious driveway leads up to a garage, with decorative stone detailing accentuating the garden area. The home is framed by palm trees, contributing to the tropical ambiance.

5.0 out of 5 average rating, 137 reviews

Sunrise Villa - Tropical 3 bedroom home with pool

ValueLocationCheck-in

5.0 out of 5 average rating, 5 reviews

Beachfront · Heated Pool & Spa · Balcony Views

LocationFamilyGetting around

5.0 out of 5 average rating, 20 reviews

Coastal Luxe Pool Home | Near Anna Maria Island

LocationFamilyHot tub

A serene backyard scene is highlighted by a sparkling pool, accompanied by lounge chairs and a hammock nestled among lush trees. The stylish bungalow features a spacious deck, creating an inviting atmosphere for outdoor relaxation. The sky is painted in calming hues as sunset approaches.

4.97 out of 5 average rating, 65 reviews

10 min AMI | 15 min IMG | Heated Pool

LocationFamilyCleanliness

Condo rentals with a pool

A balcony offers a serene view of the Gulf of Mexico, featuring a lounge chair positioned for relaxation. The space is framed by a white railing, with sandy beach and greenery visible in the distance under a bright sky dotted with clouds.

4.85 out of 5 average rating, 121 reviews

Oceanfront Condo for Beach Lovers

FamilyValueCondition

4.98 out of 5 average rating, 112 reviews

Condo in Longboat Key

Beach Condo with Quiet, Private Beach

FamilyLocationLayout

4.87 out of 5 average rating, 108 reviews

Anna Maria Island 1 BR Condo

LocationFamilyAccuracy

4.86 out of 5 average rating, 124 reviews

A shared pool area is framed by a well-maintained deck and lounge chairs. The light-colored building features balconies and is surrounded by palm trees and landscaping. Clear blue skies enhance the inviting atmosphere of the outdoor space.

Condo in Holmes Beach

Beachfront 1BR with pool

ValueLocationWalkability

4.98 out of 5 average rating, 258 reviews

A dining setting on a patio table showcases a plate of breakfast foods, including a toasted bagel, fruit, and a drink. Soft, rolled towels are stacked nearby, with a view of the beach and pool visible in the background.

Condo in Longboat Key

Direct Oceanview: Open October 26th - 29th!

LocationFamilyLong stay

4.96 out of 5 average rating, 53 reviews

~Hot Dates, Cool Prices – Beach Access - Lrg Pool~

LocationValueBiking

A spacious heated pool is illuminated in a calming blue hue, surrounded by lounge chairs and tropical landscaping. The backdrop features the condo buildings, creating a serene ambiance for evening relaxation.

5.0 out of 5 average rating, 52 reviews

AMI Perfect Experience

LocationValueView

Superhost

5.0 out of 5 average rating, 4 reviews

Beachfront Studio on Anna Maria Island

LocationBeachComfort

Other vacation rentals with a pool

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!

ValueFamilyGrill

4.95 out of 5 average rating, 74 reviews

Apartment in Bradenton Beach

Bayfront 2BR | Heated Pool | Walk to Beach

ValueFamilyCleanliness

5.0 out of 5 average rating, 21 reviews

Townhouse in Bradenton Beach

1-Min Walk to Beach | Anna Maria Island

ValueLocationPool

5.0 out of 5 average rating, 31 reviews

Apartment in Bradenton Beach

A cozy studio space is depicted, featuring a spacious king bed adorned with fresh linens. A comfortable sofa sits nearby, complemented by a decorative pillow. A blue side table and an upholstered ottoman add color to the room, which is illuminated by natural light through the sheer curtains.

Coconut Vacation Rentals/Studio/Steps to Beach!

ValueLocationCondition

4.98 out of 5 average rating, 49 reviews

4.74 out of 5 average rating, 54 reviews

Mermaid Tale by Duncan Real Estate

FamilyValueBeach

4.97 out of 5 average rating, 34 reviews

Game Room, Heated Pool & Putting Green! Sleeps 15!

FamilyLocationDecor

A bright and spacious retreat features a heated pool within a screened enclosure, allowing for outdoor enjoyment. The living area showcases modern decor with ample natural light. The kitchen offers sleek cabinets and countertops, while a cozy sleeping area presents a well-dressed spacious bed for comfort.

4.94 out of 5 average rating, 87 reviews

Pets Are Welcome/ Heated Pool/ Close to AMI

LocationFamilyNearby

Superhost