Vacation rentals with a pool in Cortez

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

Immerse in fun at the charming Cortez Cottage in Bradenton! Enjoy close proximity to the beach and seafood restaurants, plus an outdoor oasis with a heated pool, hot tub, BBQ grill, fire pit, 65" outdoor TV, pickleball, ping pong, and cornhole. Clean and fully equipped, our 3-bedroom home sleeps 11. Praised for our cleanliness and hospitality, we have all you need for an unforgettable family vacation. Join our delighted guests: book your stay at Cortez Cottage, where the beach meets family fun!.

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

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

A charming coastal haven with saltwater pool, grill, balcony & AC. Prime locale near the historic Cortez Village, a short stroll from Palma Sola Bay for kayaking and paddleboarding, and less than two miles from the Cortez Bridge and white sand beaches of Anna Maria Island. Have fun collecting shells and building sandcastles while on the lookout for dolphins and manatees. Enjoy sunbathing after a swim in the pool. The bright open floor plan is a lovely retreat after a day of sun, sand and surf!

4.88 out of 5 average rating, 112 reviews

#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!

An open-concept living space features a dining area with a round table and four chairs, adjacent to a modern kitchen equipped with stainless steel appliances. A large, comfortable sofa is visible in the living area, with natural light streaming through window blinds.

4.92 out of 5 average rating, 118 reviews

"Manatee" 3 miles to Anna Marie

Heated, Shared Pool! More affordable & away from the congestion at Anna Maria Island & still close enough to drive (Only 3 miles). Lots of Restaurants & Shopping Nearby. The Manatee Duplex offers 2 Full Baths, 2 Bedrooms, A Large Sofa Sleeper, Full/Twin Bunkbed/Daybed in the Florida Room. Comfortably Sleeps 6-8 People. Big Fenced in Private Backyard, Patio, Table, Chairs, Umbrella, Sun Loungers, Gas Grill, Beach Accessories to take to the Nearby Beaches. Plenty of Parking for a Boat/Trailer.

4.97 out of 5 average rating, 32 reviews

Canal Retreat: Heated Pool • Dock • Kayaks • Bikes

Wake up to canal views, explore the mangroves on a kayak, and unwind in your private pool after a beach day on Anna Maria Island. Or, explore the neighborhood on bike.Your perfect Gulf Coast getaway starts here! Why you’ll love it: Private dock for fishing and mooring your boat Use of one tandem kayak and two bicycles included for your stay Heated, sparkling screened pool 3 sleep spaces: 2 spacious bedrooms and 1 cozy bunk room Fully stocked kitchen 5 min to shops, dining & IMG Academy

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, 129 reviews

Sunrise Villa - Tropical 3 bedroom home with pool

Relax with the family at this tropical oasis. Sunrise Villa sits in the corner of a quiet cul-de-sac, just a quarter mile from Palma Sola Bay and 5 miles from the quaint island of Anna Maria and its sandy white beaches. Enjoy the tropical backyard paradise and the abundance of restaurants, beaches, and entertainment in close proximity. Lounge by the pool, take a bike ride along the bay, take a short bike/car ride over to the island, or take a short car ride to downtown Bradenton.

An outdoor pool area is enclosed with a screened lanai, featuring a clear blue pool with a sun shelf. Comfortable seating is provided nearby, along with a barbecue grill. Lush palm trees and a canal view are visible in the background.

5.0 out of 5 average rating, 70 reviews

3BR/3BA + Waterfront! Hot tub + Pool + Beaches!

🌊🌴Welcome to Kingston’s Hideaway, a beautiful waterfront oasis just 2 miles from the pristine Gulf beaches of Anna Maria Island! Whether you're seeking relaxation, adventure, or a bit of both, this home offers a tranquil and luxurious escape for your next vacation! Waterfront Canal: Direct access for boating and paddleboarding-(1 paddle board available for use) Private Dock: Conveniently dock your boat right at the house (27 ft max) Pool & Hot Tub: Relax and rejuvenate.

4.91 out of 5 average rating, 22 reviews

Rustic Coastal Escape| Pool | Fire Pit

Welcome to Rustic Coastal Escape, a charming 3-bedroom, 2-bath retreat inspired by relaxed beach living and vintage coastal style nestled in historic Cortez village. Thoughtfully decorated with rustic touches and coastal décor throughout, this home offers a warm, inviting atmosphere perfect for families, couples, and friends looking to unwind near Florida’s Gulf Coast. The beach is just a 2 minute drive or just a 15 to 20 minute walk away.

5.0 out of 5 average rating, 10 reviews

The Lazy Turtle ~ Canal-Front Retreat

The Lazy Turtle offers bright, spacious indoor and outdoor living spaces with plenty of room for the whole family to unwind! Enjoy the private pool, personal putting green, and peaceful canal-front backyard--perfect for fishing, kayaking, viewing wildlife, or docking your own boat. Located near the sugar-sand beaches of AMI and the charming coastal city, Bradenton, it's the perfect place to relax and enjoy sunny Florida!

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

Welcome to Dockside Dreams - Your Waterfront Paradise! Escape to our home nestled along the serene waters, less then 3 miles from Bradenton Beach. This is not just a vacation; its an aquatic adventure waiting for you! - Private Boat Dock - Dolphin and Manatee Sighting! - Close to the Beach! - Fully Equipped Kitchen - Outdoor Oasis: Soak up the sun on your deck or cook out by the water! Stays of 28+ Days welcome on request!

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

Escape to your own private Old Florida oasis where swaying palms, a heated pool wrapped by a freshwater stream, and an outdoor kitchen with TV set the scene for an unforgettable group getaway. Fire pit evenings, beach days with gear provided, and a fully fenced backyard make this the ideal base for families and groups. Pet and toddler friendly. Seven minutes to IMG Academy and ten minutes to Anna Maria Island beaches.

Popular amenities for Cortez rentals with a pool

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

House rentals with a pool

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.

4.91 out of 5 average rating, 426 reviews

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

5.0 out of 5 average rating, 102 reviews

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

4.94 out of 5 average rating, 32 reviews

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

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, 25 reviews

Bayview Pointe! Luxury Villa near Anna Maria isle!

4.98 out of 5 average rating, 60 reviews

Heated saltwater CAGED pool ! NEW ! CLEAN !

An outdoor area features a heated pool surrounded by lounge chairs and umbrellas. A fire pit is positioned in front of a seating arrangement, creating a cozy gathering spot. Soft lighting from string lights adds ambiance to the serene space, enhanced by lush greenery.

5.0 out of 5 average rating, 60 reviews

Blessed Haven Peaceful Getaway 3 Miles to Beach

4.87 out of 5 average rating, 15 reviews

Canalfront! Pool, Dock, Near Anna Maria Island

5.0 out of 5 average rating, 7 reviews

Cortez Boat Resort by AMIsland White Sand Beaches

Condo rentals with a pool

4.96 out of 5 average rating, 111 reviews

Steps to the beach! Condo with pool at The Terrace

4.85 out of 5 average rating, 102 reviews

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.

Condo in Bradenton Beach

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

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

4.99 out of 5 average rating, 182 reviews

Condo in Longboat Key

Sunny Days on LBK!

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.

4.99 out of 5 average rating, 159 reviews

Short Stroll to the Surf! ~ Make Memories on AMI

4.98 out of 5 average rating, 109 reviews

Condo in Longboat Key

Beach Condo with Quiet, Private Beach

A heated pool is surrounded by lush greenery and palm trees. Lounge chairs are positioned along the perimeter, and a gentle blue hue reflects off the water. The two-story buildings in the background create a tranquil resort-like setting.

4.97 out of 5 average rating, 137 reviews

NEW listing on AMI! Walk to fabulous beach front!

4.92 out of 5 average rating, 125 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.

Condo in Bradenton Beach

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

Other vacation rentals with a pool

4.9 out of 5 average rating, 42 reviews

The resort-style backyard features a spacious saltwater pool surrounded by palm trees. Colorful lounge chairs are positioned around the pool, and an umbrella offers shade. A covered dining area with tables is visible along the side of the property, inviting relaxation and enjoyment.

Condo in Cortez

Tropical Haven *B

5.0 out of 5 average rating, 10 reviews

Sea La Vie ~ Heated Pool Oasis!

A tranquil pool area is highlighted by clear, blue water, gently illuminated in soft shades. Comfortable lounge chairs are positioned nearby, surrounded by lush greenery and decorative lighting. Soft sunlight casts a warm glow over the scene, creating a relaxing environment.

4.71 out of 5 average rating, 34 reviews

Paradise Inn

5.0 out of 5 average rating, 27 reviews

85" TVs*GLOW in the dark Game Rm*Pool Table*POOL

5.0 out of 5 average rating, 11 reviews

Home in Holmes Beach

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

5.0 out of 5 average rating, 4 reviews

Relax & Reconnect-Pool & Waterview

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.

4.93 out of 5 average rating, 83 reviews

Pets Are Welcome/ Heated Pool/ Close to AMI