Vacation rentals with a pool in Estero Bay

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Top-rated rentals with a pool in Estero Bay

Guests agree: these homes with a pool are highly rated for location, cleanliness, and more.

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Top guest favorite

Home in Bonita Springs

Remodeled 4 BR 3 Full Bath Sunshine Getaway

A perfect place for couple's or families. This home boasts 2 master suites with large, covered Lani with heated pool (Nov-March 85°). A total of 7 smart TVs. Enjoy preparing a family meal in the large fully equipped kitchen with double oven and plenty of counter space. Enjoy a bike ride on one of 4 bikes or Cornhole that's provided as well as other games and beach accessories. House sits on a quiet cul-de-sac for relaxing. Absolutely no parties or events! Max Guests on property at ANY time is 8!

LocationValueBeach

5.0 out of 5 average rating, 102 reviews

Top guest favorite

The screened-in pool area features a serene swimming pool with shimmering water, two blue lounge chairs positioned nearby, and views of a wide canal. A thatched-roof Tiki hut can be seen across the water, surrounded by lush greenery.

Home in Pelican

LUX Villa w/ Private Salt Water Pool, Lanai, Canal

Are you looking to swim, relax outdoors, fish and take in beautiful sunsets on a wide gulf access canal? If so you will fall in love with this stunning newly constructed custom built home! The 2750 square foot home is bright & airy with two main bedroom on-suites & a separate family wing! The gourmet kitchen, dining room & great room open via large sliders to the lanai & pool w/ views of the canal in much desired SW Cape! Beach inspired villa! Large captains walk & Tiki! Check out our reviews!

LocationFamilyLayout

4.99 out of 5 average rating, 266 reviews

Guest favorite

The outdoor area showcases a large pool surrounded by stone patio flooring. Comfortable lounge chairs are positioned beside the pool. Lush greenery and palm trees frame the space, contributing to a private and tranquil setting.

Home in Fort Myers

Paradise on Estero Bay

Welcome to Mullock Creek a Boater's dream! Southwest views boasting breathtaking sunsets overlooking gulf access canal from your spacious backyard, just minutes away from shopping and dining at Coconut Point, and Gulf Coast Town Center. This stunning Key West Style home has been beautifully maintained and updated offering a lovely front entrance, fully equipped kitchen, spacious Living Room, dining room, Wi-Fi, private driveway with access to the open garage, fully furnished and private pool.

FamilyLocationDecor

4.95 out of 5 average rating, 164 reviews

Top guest favorite

Home in Bonita Beach

"The Mac" Beach House! Premier Location! Pool/Spa

Breathtaking sunsets await from the second story and third story lanais overlooking the beautiful bay. This gorgeous Spanish-style home located steps from the white sand at Bonita Beach provides a perfect getaway for groups of all sizes! This home features a premier location and luxury stay all in one! Walk to the beach and enjoy food, drinks, paddleboard, jet ski or lounge rentals just a few steps away at Doc's Beach House or stroll down to great local restaurants just mins from the door.

FamilyLocationTV

4.99 out of 5 average rating, 106 reviews

Guest favorite

The lanai area features a heated saltwater pool, complemented by a cozy seating arrangement, dining table, and a hammock. Ample natural light enters through the screened enclosure, highlighting the inviting atmosphere. Tropical greenery is visible beyond the curved arches, enhancing the outdoor living space.

Home in Bonita Springs

Heated Saltwater Pool Oasis, Lanai, Bonita Springs

Heated saltwater pool with no extra fees, relaxing screened lanai, and true Florida outdoor living with a wet bar, refrigerator, grill, hammock, dining area, large screen TV, sound system, and comfortable lounge seating. With 4 bedrooms and 3 bathrooms, Casa Del Sol is a peaceful private oasis just 3 miles from Bonita Beach and 1 mile from downtown Bonita Springs’ restaurants, bars, shops, and attractions. The perfect place to relax, recharge, and enjoy Southwest Florida living year-round.

FamilyValueGetting around

4.97 out of 5 average rating, 113 reviews

Top guest favorite

A screened patio overlooks a serene swimming pool surrounded by lush greenery. Two lounge chairs are positioned nearby, with a small table featuring colorful drinks. A few inflatable toys float in the water, offering a casual ambiance for relaxation.

Home in Bonita Springs

3BR w/HUGE 2k sq ft Lanai & Seasonally Heated Pool

Welcome to your peaceful Bonita Springs retreat, perfectly located near Naples, Ft. Myers, shopping & beaches! This isn’t just a rental, it’s our 2nd home and we treat it as such. You'll experience "exceptional" the minute you enter this stunning, open concept interior. Further, it boasts a striking 2000 sq ft screened-in lanai w a seasonally heated pool. This outdoor oasis doubles your living space and offers a flying pest barrier and significant UV protection. Breathe/Smile/Unwind

LocationFamilyLong stay

4.98 out of 5 average rating, 132 reviews

Top guest favorite

A spacious private pool area features a heated pool and spa, enclosed by a screen for comfort. Lush greenery is visible through the arches, enhancing the serene setting. Modern lounge seating is positioned nearby, inviting relaxation and enjoyment.

Home in North Naples

Luxurious Naples Home. Heated Pool. Mins to Beach.

Have fun with the whole family at this stylish Naples Costal Paradise Home. Tropical Oasis within minutes to the beaches, restaurants, shopping, entertainment. Heated pool, Wi-Fi, big lanai with BBQ and more. House is a 3-bedroom, 2-bathrooms fully renovated in coastal contemporary style with tile floors, coastal art, big kitchen and more. King bed, queen bed, 2 full beds, big modular couch. House will comfortably sleep 6 adults plus children. It has all you need for great vacation.

LocationValueWifi

4.98 out of 5 average rating, 122 reviews

Top guest favorite

A spacious living area is presented with two gray sofas and two blue armchairs arranged around a decorative coffee table. A large television is mounted on the wall, and natural light filters through the plantation shutters, illuminating the room's light-colored tile flooring.

Home in Bonita Springs

Bonita Retreat: Heated Pool - Minutes to Beach

We know that you’ll love it here – whether you spend your time lounging by our pool, or at beautiful Barefoot Beach, less than 3 miles away. Our home is close to everything, so many beautiful beaches, great shopping and world class restaurants. If dining-in is more your thing, you will have a fully stocked kitchen with every amenity you could wish for. This is our own vacation home, so we’ve made every effort to make it as comfortable and convenient as possible.

ValueFamilyPets

4.99 out of 5 average rating, 151 reviews

Top guest favorite

Home in Fort Myers

Whole cozy house

Entire cozy house just for you friends and family. Perfect to spend a pleasant and relaxed moment. If you plan to have a party or event, this place is NOT for you. The neighbors are very strict in terms of noise and large groups of people. Well maintained house. CLEAN POOL BUT NOT HEATED. Walk in to a living area and separated dining. 20 minutes to airport, 25 minutes to the beach, fine dining and entertainment. For a virtual tour, click on the cover photo twice.

FamilyValueNearby

4.95 out of 5 average rating, 410 reviews

Top guest favorite

A heated pool is bordered by a spacious deck featuring sun loungers and an umbrella. A pergola with hanging lights provides a shaded dining area with a grill. Lush landscaping surrounds the pool, enhancing the outdoor space for relaxation and entertainment.

Home in Naples Park

673 Lazy Beach Daze · Heated Pool · Walk 2 Beaches

Welcome to your 673 Lazy Beach Daze; your dream coastal getaway! This stunning 3BD, 3 1/2BA vacation rental home is a luxurious retreat nestled in the heart of North Naples, a picturesque coastal paradise. As you arrive, you'll be greeted by the gentle rustle of palm trees, setting the tone for a relaxing escape. This gorgeous home is located just a mile from the relaxing white sands of Bluebill Beach; perfect for an evening stroll or early morning bike ride!

FamilyLocationCondition

4.98 out of 5 average rating, 113 reviews

Superhost

A clear blue pool is surrounded by lush palm trees and a rock waterfall, offering a serene atmosphere. Comfortable lounge chairs are positioned nearby, overlooking a tranquil waterway, enhancing the outdoor leisure space.

Condo in Fort Myers Beach

Lovers Key Resort, Fort Myers Beach - Awesome

Fort Myers Beach and Lovers Key State Park are what you come to Florida for. Miles of Pristine beaches with the lovely white sand you want to walk upon. Great hiking and biking trails. A plethora of restaurants and things to do. Watch the Dolfins playing in the bay from your balcony. The wildlife is beautiful all times of the year and of course the Beach. Big wide stretches of beach to walk and play on. Come to Ft Myers Beach and ENJOY

ValueLocationGetting around

4.81 out of 5 average rating, 185 reviews

Top guest favorite

Home in Naples Park

Walk to The Ritz & Beaches, 2 Mstrs w Kings, Pets

Fabulous 500 block location. Just a short walk/bike ride to the beach. This exclusive layout w 2 master suites, large walk-in closets, and private baths. Every living space has been thoughtfully designed for large groups of 8-10 to gather and enjoy. The house is fully stocked. This includes a coffee maker, dishes, pots and pans, beach cruiser bikes, beach chairs, a wagon, etc. All you need is to pack your bags, sit back and relax...

LocationFamilyBiking

4.99 out of 5 average rating, 156 reviews