Home rentals with a pool near Cortez Beach

A three-level coastal villa is showcased, featuring a light grey exterior and multiple balconies with white railings. Lush green landscaping surrounds the property, and a paved driveway leads to the private garage. Palm trees add a tropical touch to the inviting entrance.

5.0 out of 5 average rating, 19 reviews

Coastal Luxe Villa! Near AMI

Welcome to Coastal Luxe Villa, your perfect Florida escape—nestled in historic Cortez and just minutes from the sandy shores of Anna Maria Island. This spacious three-level coastal retreat combines modern comfort with beach-town charm, offering stunning bay views and endless amenities for unforgettable memories. Private garage with a bonus table tennis setup Sparkling heated saltwater pool with outdoor seating, dining, firepit table, and gas grill Convenient elevator access to all three floors

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.

4.94 out of 5 average rating, 198 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.

4.96 out of 5 average rating, 112 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!

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!

4.91 out of 5 average rating, 128 reviews

4.76 out of 5 average rating, 84 reviews

AMI Cortez Beach Retreat Poolside Resort-stylePool

Resort-style Heated Pool w/ "Views Over the Water" at Beach + Bay Home - duplex upstairs unit • 65 steps to Cortez Beach + 7 miles of white Anna Maria Island sand! • $150,000 new large, heated pool with salt-water, spillover spa, sitting shelf, +built-in umbrellas. • Gulf + Beach + Bay Views inside home + deck • Paddleboard + Kayak • High-speed WiFi • 3 blocks to Bridge Street restaurants/bars/pier/shopping + listen to the Bell Tower Clock ringing each hour – live music! • Ping pong table

5.0 out of 5 average rating, 28 reviews

New! 4BR Villa + Crosswalk to Sand + Beach View!

Location ‼️ Location ‼️ 🌟🌴Welcome to Starfish Villa East, this Beachside home offers a private pool, putting green, & balconies with partial Gulf views. 🏖️Unwind across from the beach and fishing pier, and blocks from Bridge Street fun! ⛱️ Beach supplies included: wagon, 8 chairs, umbrella, cooler, and towels – everything you need for a perfect beach day 💃 Walking distance to Bridge Street, where you’ll find restaurants, shopping, bars, live music, attractions, ice cream, & mini g

An aerial view of a coastal condo complex showcases a well-maintained tennis court in the foreground, adjacent to a sparkling pool area. Expansive ocean views are visible in the background, highlighting the proximity to the beach. Lush palm trees provide greenery around the facilities.

5.0 out of 5 average rating, 7 reviews

Island Escape Beach Pool Hot Tub WATER VIEWS

🏖️ Charming 2-bedroom, 2-bath condo just steps from the sand and pier 🌅 Two screened lanais with both sunrise and sunset views 📍 Prime location between Bridge Street & Coquina Beach 🚋 Trolley stop & Gulf Drive walkway right outside the complex 🏊 Amenities include pool, spa, tennis, pickleball, fishing pier & grills 🏘️ Quiet, boutique 16-unit complex 🚲 Easy access to local attractions with the free island shuttle 🤝 Local hosts nearby and happy to help during your stay

4.79 out of 5 average rating, 34 reviews

Playa Esmeralda Home! And add a golf cart!

Our beach home rental boasts 5 bedrooms, 5 1/2 bathrooms we Accommodate up to 12 P, hot tub, bar, play area, full kitchen, and an amazing rooftop with ocean views! Located only two blocks from the beach and just one block from restaurants and shops, this vacation rental has everything you need for a relaxing and fun getaway. Whether you're planning a family vacation, a girls' trip, or a reunion with friends, this beach house has plenty of space to accommodate everyone comfortably.

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, 205 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.

4.73 out of 5 average rating, 51 reviews

Mermaid Tale by Duncan Real Estate

Welcome to Mermaid Tale! Relax stress-free in this two-bedroom accommodation which is on the top floor of this cute vacation triplex, only 5 houses from the Bradenton Beach gulf beaches and walking distance to restaurants, bars and shopping. Mermaid Tale is very comfortably located close to Bridge Street. Mermaid Tale is a great getaway for 4 people. Walk up the stairs to the first floor entrance and be greeted by coastal flair. The kitchen is fully equipped.

4.97 out of 5 average rating, 212 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.

4.67 out of 5 average rating, 12 reviews

Seaside Manor! Pool, Spa and Beach Walk!

Seaside Manor by Anna Maria Island Accommodations TPL21-000096, DWE5105083 Welcome to Seaside Manor, a beautifully updated 3-bedroom, 2-bathroom vacation home just a two-minute walk from the sugar-white sands of Bradenton Beach. With a private pool and spa, multiple living spaces, and a location steps from the free island trolley, this home is the perfect spot for families and friends looking for a relaxed Anna Maria Island escape.

Popular amenities for rentals with a pool near Cortez Beach

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

House rentals with a pool

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.

4.98 out of 5 average rating, 107 reviews

Dockside Dreams - Pool, Spa & Waterfront Dock

4.99 out of 5 average rating, 103 reviews

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.

Home in Bradenton

Heated Pool | Game Room | Arcade | Sleeps14 | BBQ

4.97 out of 5 average rating, 39 reviews

Casa Bonita

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, 99 reviews

Spectacular Beach/Bay views private pool elevator

An aerial view captures a modern three-level home featuring multiple balconies and a sparkling heated pool on the lower level. The surrounding landscape includes lush greenery, with the bay visible in the background, creating a serene ambiance during dusk.

4.96 out of 5 average rating, 26 reviews

Bayview Pointe! Luxury Villa near Anna Maria isle!

A screened enclosure surrounds a private swimming pool, providing a sunny outdoor space. Comfortable seating is visible alongside a dining area with a table and chairs. Lush greenery and palm trees can be seen in the background, enhancing the tropical atmosphere.

4.98 out of 5 average rating, 40 reviews

“Topside” luxury home in Cortez Village

4.92 out of 5 average rating, 24 reviews

Rustic Coastal Escape| Pool | Fire Pit

5.0 out of 5 average rating, 8 reviews

Family Tides B – AMI Retreat, Pool & Rooftop Deck

Condo rentals with a pool

4.98 out of 5 average rating, 110 reviews

Condo in Longboat Key

Beach Condo with Quiet, Private Beach

4.77 out of 5 average rating, 150 reviews

Cute 1Bedroom Beach condo, only steps from beach!

4.98 out of 5 average rating, 258 reviews

Condo in Longboat Key

Island Time: Open Tues - Sat!

4.87 out of 5 average rating, 108 reviews

Anna Maria Island 1 BR Condo

4.88 out of 5 average rating, 139 reviews

Condo in Longboat Key

Sunset and beach view from your balcony Unit 403

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, 128 reviews

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

5.0 out of 5 average rating, 4 reviews

Bayfront - Pelican Cove 16 by SeaBreeze Vacation

A wooden walkway leads from a palm tree-lined entrance to a sandy beach. The ocean is visible in the background, showcasing rolling waves under a clear blue sky. Gentle sunlight illuminates the natural landscape, highlighting the serene environment.

4.92 out of 5 average rating, 51 reviews

Sandcastle Dreams

Other vacation rentals with a pool

Apartment in Bradenton Beach

Bayfront 2BR | Heated Pool | Walk to Beach

5.0 out of 5 average rating, 20 reviews

Townhouse in Bradenton Beach

Bay & Gulf Views. Waterfront+heated pool+AC

4.91 out of 5 average rating, 11 reviews

Townhouse in Bradenton Beach

1-Min Walk to Beach | Anna Maria Island

5.0 out of 5 average rating, 29 reviews

4.86 out of 5 average rating, 49 reviews

The image showcases a saltwater pool surrounded by a manicured grassy area. Two aqua-colored loungers are positioned near the pool, while a bright umbrella adds shade. The duplex structure features multiple balconies and a spacious outdoor area, creating an inviting atmosphere for relaxation.

Vacation home in Cortez

Manatee Manor

Apartment in Longboat Key

New Modern on Beach- Walk out 5 steps to Sand

5.0 out of 5 average rating, 43 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!

4.98 out of 5 average rating, 48 reviews

4.97 out of 5 average rating, 62 reviews

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.

Home in Bradenton

10 min AMI | 15 min IMG | Heated Pool