Home rentals with a pool near Cortez Beach

4.98 out of 5 average rating, 113 reviews

Walk to it all! Restaurants + Heated Pool +Beach!

🌊🏖️Welcome to Making Waves on Anna Maria Island-where you are steps from the beach and centrally located to it all, footsteps to the trolley stop! Escape to paradise and experience the ultimate beach getaway at this stylish beach house with heated pool, nestled in the heart of Anna Maria. Walk outside the door to the pristine beaches, renowned local restaurants, and the vibrant Bridge Street with live music, restaurants, bars, and shopping. Our beach retreat promises an unforgettable vacation!

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

A serene view from a balcony is presented, showcasing calm waters and lush greenery along the shoreline. Two wicker chairs and a round table are positioned on the balcony, enhancing the inviting outdoor space. The sky is clear, reflecting soft natural light on the water.

4.85 out of 5 average rating, 102 reviews

Charming 2BD/2BR with Big Water Views on the beach

Our charming 2 BR/ 2 Bath condo has wonderful unobstructed views of Anna Maria Sound. It was totally remodeled in 2020. The property is in the Bradenton Beach area of Anna Maria Island. The Beach is right across the street with deeded access. The pool is the largest heated pool on the island. Bikes and kayaks are included. A free trolley stop is right in front of the property. There is a washer/dryer in the unit. The 2nd bedroom has both a queen bed and a bunk bed for larger parties.

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, 195 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.

Apartment 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!

4.96 out of 5 average rating, 111 reviews

4.89 out of 5 average rating, 54 reviews

AMI Dock of the Bay - "On the Water" 1st Floor

AMI Beach + Bay Home with Fishing Pier + Heated Pool on Sarasota Bay - "Dock of the Bay" / Entire 1st floor of Duplex called "On the Water" • Unbelievable views of water + birds + wildlife + night lights! • Relax with fish jumping and birds flying along 1 of only 34 coveted docks/piers south of Cortez Bridge! • Fish off dock and rod holders! • Heated pool w/ spa jets/benches only 10 ft from Bay! • Walk 2 blocks to Bridge Street/Key West-style restaurants, bars. • Live Music heard on dock!

Apartment 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!

4.88 out of 5 average rating, 112 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!

4.91 out of 5 average rating, 127 reviews

5.0 out of 5 average rating, 26 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, 6 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

4.64 out of 5 average rating, 86 reviews

Seahorse Suite by Duncan Real Estate

Welcome to Seahorse Suite! This efficiency is located in a triplex in Bradenton Beach on a quiet dead end street within a short walk to Bridge Street. It is one of the 2 ground level rental units with the upstairs being used privately. The property sits only 5 houses from the Gulf Beaches and 2 houses from the Bay side. This little efficiency is the just the right size for one guest or a couple to enjoy a great island getaway.

4.87 out of 5 average rating, 107 reviews

Anna Maria Island 1 BR Condo

Reserve some relaxation now. 2 blocks from historic Bridge Street pier and beach! Convenient walk to restaurants, outdoor music spots, putt putt golf and local shops. Free trolley ride at the corner of Gulf Blvd every 20 minutes. BBQ grill for outdoor cooking at the pool area. New ferry boat at the pier to enjoy a ride to downtown Bradenton.

Popular amenities for rentals with a pool near Cortez Beach

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

House rentals with a pool

4.99 out of 5 average rating, 142 reviews

Pickleball, Game Room, Heated Pool, 4 Min to Beach

An outdoor space features a newly constructed pickleball court, complemented by a heated pool and a raised deck. Surrounding tropical foliage provides a natural backdrop, while a vibrant sunset casts a warm glow over the setting.

4.98 out of 5 average rating, 100 reviews

Cottage w/ Pickleball Outdoor Oasis 2 mi to Beach

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, 202 reviews

STEPs to BEACH! /Heated Salt Pool/Sunsets/5 STAR!

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, 103 reviews

Dockside Dreams - Pool, Spa & Waterfront Dock

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

An aerial view captures a tranquil heated pool surrounded by lush tropical greenery. Two white lounge chairs are positioned beside the water, and steps lead up from the pool area. A variety of palm trees and tropical plants create a serene atmosphere.

4.94 out of 5 average rating, 183 reviews

Big Backyard Pool Retreat Near IMG Academy, Beach

4.94 out of 5 average rating, 127 reviews

An inviting outdoor pool area features upgraded lounge chairs set beside a clear, private pool. A dining space is positioned under the screened enclosure, allowing for enjoyable gatherings. The sunset sky in the background adds a tranquil ambiance, enhancing the outdoor relaxing experience.

Home in Bradenton

Tropical Getaway: Pool, Putting Green,Near Beaches

4.97 out of 5 average rating, 37 reviews

Beautiful House

Apartment rentals with a pool

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, 125 reviews

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

Apartment in Longboat Key

Sunny Days on LBK!

4.99 out of 5 average rating, 182 reviews

Apartment in Holmes Beach

A modern kitchen area features pale blue walls and a round dining table set for four. Stainless steel appliances, including a microwave and oven, are visible. A decorative light fixture made of translucent discs hangs above the table, adding a coastal touch to the space.

Short Stroll to the Surf! ~ Make Memories on AMI

4.99 out of 5 average rating, 159 reviews

Apartment in Longboat Key

Beach Condo with Quiet, Private Beach

4.98 out of 5 average rating, 109 reviews

4.76 out of 5 average rating, 143 reviews

Cute 1Bedroom Beach condo, only steps from beach!

Apartment in Longboat Key

Beachfront Escape – Private Balcony, Gulf Views

4.89 out of 5 average rating, 126 reviews

4.8 out of 5 average rating, 5 reviews

Pelican Cove 1 - Anna Maria Island - Condo 2 Bedro

5.0 out of 5 average rating, 3 reviews

Bayfront - Pelican Cove 16 by SeaBreeze Vacation

Other holiday rentals with a pool

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.

4.97 out of 5 average rating, 37 reviews

“Topside” luxury home in Cortez Village

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, 98 reviews

Spectacular Beach/Bay views private pool elevator

5.0 out of 5 average rating, 18 reviews

Flat in Bradenton Beach

Bayfront 2BR | Heated Pool | Walk to Beach

4.94 out of 5 average rating, 32 reviews

Island Adjacent! 4 bed/3 bath home w/Pool & Tiki!

Townhouse in Bradenton Beach

1-Min Walk to Beach | Anna Maria Island

5.0 out of 5 average rating, 28 reviews

4.91 out of 5 average rating, 22 reviews

Rustic Coastal Escape| Pool | Fire Pit

5.0 out of 5 average rating, 11 reviews

Home in Holmes Beach

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