Vacation rentals with a pool in Cortez

4.98 out of 5 average rating, 114 reviews

An aerial view captures a heated private pool surrounded by tropical landscaping. Deck chairs and a lounge chair provide seating options, and stone pathways lead to the pool. The pool curves gracefully, inviting relaxation in a serene outdoor setting.

Home in Bradenton Beach

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!

FamilyValueDecor

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, 101 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!.

FamilyValueCheck-in

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

LocationFamilyAmenities

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, 123 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

FamilyValueAccuracy

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, 119 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.

LocationFamilyGetting around

4.5 out of 5 average rating, 4 reviews

Home with Pool and Elevator! Near Anna Maria Sound

The Renata at Hunter’s Point by AMI Locals Experience the perfect blend of eco-luxury and modern comfort at The Renata, a brand-new home nestled in the heart of Hunter’s Point! This stunning three bedroom, two and half bath retreat features a private pool, elevated balcony with water views, and an elevator for effortless access. Surrounded by natural waterways, the home is just under a mile from the beautiful beaches of Anna Maria Island, making it an ideal sanctuary for relaxation, water

LocationFamilyAmenities

4.97 out of 5 average rating, 33 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

FamilyLocationCleanliness

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, 132 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.

LocationValueComfort

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.

FamilyLocationNearby

4.92 out of 5 average rating, 24 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.

LocationFamilyCondition

4.91 out of 5 average rating, 152 reviews

A fire table is positioned in view of a vibrant sunset, reflecting shades of orange, pink, and purple across the sky. The scene is framed by large glass panels, offering unobstructed views of the horizon, enhancing the outdoor experience.

Condo in Bradenton

New Luxury 3/3 Condo in Margaritaville Resort

Our luxury 3 BR/ 3 Bath Margaritaville inspired condo features wonderful unobstructed water views of Anna Maria Sound and Tampa Bay. 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.

ValueLocationOutdoor spaces

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!

LocationFamilyDecor

Popular amenities for Cortez rentals with a pool

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

House rentals with a pool

A clear blue pool reflects the sky, with four white lounge chairs arranged nearby on a sunlit patio. Lush green grass surrounds the pool area, complemented by a large tree offering shade in the background. The scene conveys a serene outdoor space for relaxation.

4.91 out of 5 average rating, 147 reviews

Palma Sola Pool Home, minutes to AMI

LocationFamilyCheck-in

4.94 out of 5 average rating, 104 reviews

Home in South Bradenton

Stylish Pool Home • Near IMG & Beaches • Top Rated

FamilyValuePool

4.98 out of 5 average rating, 61 reviews

Heated saltwater CAGED pool ! NEW ! CLEAN !

LocationFamilyView

5.0 out of 5 average rating, 10 reviews

Paradise Cove-Private Heated Pool, 3 Miles to AMI

LocationFamilyKitchen

4.94 out of 5 average rating, 33 reviews

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

FamilyLocationCheck-in

4.93 out of 5 average rating, 28 reviews

NEW Waterfront | Heated Pool | Kayaks

ValueFamilyBeach

5.0 out of 5 average rating, 7 reviews

Cortez Boat Resort by AMIsland White Sand Beaches

LocationFamilyOutdoor spaces

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, 62 reviews

Blessed Haven Peaceful Getaway 3 Miles to Beach

LocationFamilyCondition

Condo rentals with a pool

4.96 out of 5 average rating, 112 reviews

Condo in Holmes Beach

Steps to the beach! Condo with pool at The Terrace

LocationFamilyGetting around

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.

4.9 out of 5 average rating, 243 reviews

Beachfront Resort, Ocean View, Pool, Tennis, Gym

FamilyValueCleanliness

4.88 out of 5 average rating, 139 reviews

Sunset and beach view from your balcony Unit 403

ValueLocationAccess

4.98 out of 5 average rating, 110 reviews

Beach Condo with Quiet, Private Beach

LocationFamilyBathroom

4.99 out of 5 average rating, 185 reviews

Open Tonite

FamilyLocationGrill

4.94 out of 5 average rating, 143 reviews

A serene outdoor pool area is surrounded by lush tropical landscaping. The well-maintained pool is framed by the charming two-story buildings of the Palm Cay complex, with lounge chairs positioned nearby for relaxation. Palm trees sway gently in the warm sunlight.

Condo in Holmes Beach

1/1 STEPS to Beach w/ Heated POOL - Sleeps 4

ValueFamilyCondition

4.77 out of 5 average rating, 150 reviews

Condo in Bradenton Beach

Cute 1Bedroom Beach condo, only steps from beach!

FamilyLocationView

4.97 out of 5 average rating, 144 reviews

A screened lanai offers a peaceful retreat with a view of the pond and trees reflecting on the water. Comfortable seating is provided, accompanied by a small table. Natural light flows in, enhancing the serene atmosphere of the space.

Condo in Bradenton

A&A's Paradise near IMG & Anna Maria beaches

FamilyValueBathroom

Other vacation rentals with a pool

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

ValueLocationAir conditioning

4.98 out of 5 average rating, 86 reviews

Townhouse in Bradenton

Nautic Star - Large pool & Free dock and kayaks

FamilyLocationHospitality

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.

4.89 out of 5 average rating, 85 reviews

Pets Are Welcome/ Heated Pool/ Close to AMI

LocationValueAmenities

5.0 out of 5 average rating, 4 reviews

The Wabi House

LocationAccuracyHospitality

5.0 out of 5 average rating, 33 reviews

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

LocationValueDecor

4.93 out of 5 average rating, 76 reviews

Palma Sola Oasis w/ Pool | Near AMI Beaches!

FamilyValueNearby

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, 62 reviews

10 min AMI | 15 min IMG | Heated Pool

ValueLocationQuiet