Vacation rentals with a pool in Estero

5.0 out of 5 average rating, 102 reviews

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!

Guesthouse in San Carlos Park

The guesthouse exterior features a modern design with a metal roof and a two-car garage. Landscaped front yard with green grass and decorative plants is visible, creating a welcoming entrance. A secluded porch area with seating is present, surrounded by trees and shrubs.

Hezekiah's 2 Story Guesthouse with Pool

Hezekiahs Guesthouse a perfect getaway in sunny SWFL! You will be staying in the guest house with a private entrance. This property has a living room and kitchenette downstairs and a spacious bedroom with master bathroom upstairs. This Airbnb is attached to our home. You will have access to the pool and our outside grill area. Complimentary coffee, water, soda and more.. Lots of nearby restaurants and shopping. Minutes away to Fort myers or Bonita beach, FGCU and RSW Airport and Hertz Arena.

4.88 out of 5 average rating, 126 reviews

Apartment in San Carlos Park

Resort Style Pool Adj Beds-Wilder Sunset Views!

Perfectly located 2 Bedroom 2 Bath condo! Nestled on a public golf course with a wonderful pool area, it is the perfect combination for a peaceful vacation. The condo is centrally located by everything one needs to relax and enjoy the Fort Myers area. We have gone the distance to make your vacation memorable. The spacious condo has adjustable beds, which will provide you sweet dreams. Close to the beaches, shopping, airport, golf, and tons of restaurants. Guests can also enjoy the pool area.

4.93 out of 5 average rating, 135 reviews

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.

4.95 out of 5 average rating, 164 reviews

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.

4.99 out of 5 average rating, 106 reviews

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.

A bright kitchen area features a wooden countertop with a stainless steel sink and dishwasher. The space opens to a screened-in patio showcasing a heated pool and outdoor dining area, enhancing the seamless connection between indoor and outdoor living.

4.95 out of 5 average rating, 118 reviews

Classic Arcades Heated Pool Home by Beach & Dining

Escape to a relaxing beach vacation in this beautiful optional heated pool home with epic arcade game room. Includes king size beds in all bedrooms and 6 smart TVs. Features 2 family rooms and 2 fully equipped kitchens (indoor & outdoor). Offers private backyard with full outdoor kitchen, smart TV & BBQ Grill. Fully stocked home with kitchen supplies, beach essentials, bicycles, high speed internet and more. Perfect for families, couples & professionals looking for a Florida Beach Escape!

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.

4.97 out of 5 average rating, 113 reviews

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.

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.

4.98 out of 5 average rating, 132 reviews

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

The spacious living area features light-colored sofas with red accent pillows and a glass coffee table. A ceiling fan is positioned above, and natural light floods in through large windows, enhancing the welcoming atmosphere. A cozy armchair and a side table are also present.

4.96 out of 5 average rating, 106 reviews

Living on the Green

This newly renovated 3 bed 2 bath pool home is located on a lovely golf course. The pool area faces beautiful sunsets and is not heated. During the day the sun warms it to 80 unless the weather is cooler or rainy. The home is near shopping, restaurants at Gulf Town Center and Coconut Point. Beaches in Bonita or Fort Myers Beach close by. Pool table w/ table tennis option in garage. For the summer months I have added a mini-split A/C unit for the master suite for additional comfort.

A solar-heated swimming pool features clear turquoise water within a screened enclosure. Lush greenery and trees are visible in the background, complemented by soft lighting from the setting sun. A white pool edge and a handrail provide access to the water.

4.89 out of 5 average rating, 193 reviews

Bonita Oasis

Relax at the solar heated pool and enjoy the serenity of the beautiful, and peaceful 0.6 acres of land with a natural pond where different types of birds like egrets, herons, and ducks can be seen. Close to shopping, dining and just 7.5 mi to Bonita Beach Park. If you play Golf, The Bonita Fairways Public Golf Club is 2.8 mi. Or buy a day pass at the Hyatt Regency and spend the day at the lazy river and waterslides. The backyard is all fenced in, ideal to let your dog run.

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.

4.99 out of 5 average rating, 151 reviews

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.

4.95 out of 5 average rating, 410 reviews

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.

Popular amenities for Estero rentals with a pool

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

House rentals with a pool

4.9 out of 5 average rating, 161 reviews

A well-equipped kitchen features modern appliances, including a stainless steel refrigerator and microwave. Stylish pendant lights hang above a spacious island with a granite countertop. A fruit bowl adds a pop of color, while ample cabinetry provides storage space.

Home in Villas

Still available for Jan, Feb, March 2027

4.99 out of 5 average rating, 266 reviews

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

5.0 out of 5 average rating, 17 reviews

A screened-in lanai houses a private pool with clear blue waters, complemented by light-colored deck tiles. Sunlight filters through the mesh enclosure, casting playful shadows on the patio furniture, which includes reclining lounge chairs and a shaded seating area for relaxation.

Home in Estero

Relaxing Riverside Pool Home

4.96 out of 5 average rating, 45 reviews

A serene outdoor space features a sparkling pool surrounded by a spacious deck. Two lounge chairs sit beneath an umbrella, providing a relaxing area. Lush greenery forms a backdrop, with a vibrant sunset sky casting soft colors over the scene.

Home in Estero

Luxurious central POOL home, KID&PET friendly

A bright living area is decorated with a spacious brown sofa and two light grey chairs. A modern television is mounted on the wall above a dark console. Large glass doors offer views of the outdoor space, framed by light curtains. Fresh greenery is visible in the corner.

5.0 out of 5 average rating, 87 reviews

Modern Coastal Retreat / heated pool and hot tub

4.96 out of 5 average rating, 48 reviews

Family Oasis | Heated Pool + Beach Gear, Kid Ready

An open-concept living space is highlighted, featuring a large white sectional sofa and a natural wood dining table. Light-colored cabinetry and modern appliances are visible in the kitchen area, while warm tones of the flooring and decor create a welcoming atmosphere. Ceiling fans and natural light enhance the ambiance.

5.0 out of 5 average rating, 56 reviews

Modern Coastal Home w/ Pool & Game Room

A screened-in pool area features comfortable seating arranged around a fire table. The heated pool is visible in the background, framed by lush greenery outside the screened enclosure. A grill is located nearby, enhancing the outdoor space for relaxation and entertainment.

4.93 out of 5 average rating, 73 reviews

Welcome Ft Myers 3br/2ba pool vacation- dogs ok

Condo rentals with a pool

An open kitchen and dining area features a round glass table surrounded by rattan chairs adorned with tropical patterns. Stainless steel appliances are positioned next to light cabinetry. Expansive windows invite natural light, providing a view of the outdoor scenery.

4.99 out of 5 average rating, 179 reviews

Casa Bonita - Relax @ The Beach (Newly Remodeled)

A bright living area features a comfortable seating arrangement with a neutral sofa and a reclining chair. A coffee table is positioned centrally, with a scenic view of the ocean visible through expansive sliding glass doors, leading to a balcony with outdoor seating.

4.97 out of 5 average rating, 160 reviews

Bonita Beach and Tennis 3907 - Ocean Views

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

4.81 out of 5 average rating, 185 reviews

4.92 out of 5 average rating, 151 reviews

The beachfront view reveals several multi-story condominiums lining the shore, surrounded by sandy areas populated by beachgoers. Gentle waves lap at the shoreline, while a sky filled with soft clouds adds to the serene coastal atmosphere.

Condo in Bonita Springs

Ken & Gina's Beach Condo (#2301)

A scenic view showcases Bonita Beach, where the soft sand meets the calm blue waters of the Gulf. Lush palm trees line the beach, with a dining area set back from the shore. A vibrant building is visible, providing options for beachside refreshments.

4.91 out of 5 average rating, 119 reviews

Easy Breezy Too

Condo in Fort Myers Beach

A panoramic view showcases a sparkling heated swimming pool surrounded by lounge chairs, with the beach and Gulf of Mexico visible in the background. Soft waves lap at the shore while sunbathers can be seen enjoying the sandy area. Lush palm trees frame the scene.

Beachfront fully equipped apartment

4.9 out of 5 average rating, 131 reviews

A row of modern condos is situated along a sandy beach, with palm trees lining the shore and the Gulf of Mexico visible in the foreground. The sky is partly cloudy, offering a serene coastal view.

4.83 out of 5 average rating, 140 reviews

Oceanview unit. Completely remodeled pool is open!

Condo in Fort Myers Beach

Southern Comfort - Updated Waterfront Condo

4.87 out of 5 average rating, 102 reviews

Other vacation rentals with a pool

A wooden dock extends over calm waters, featuring two blue Adirondack chairs positioned for relaxation. Lush greenery and palm trees are visible in the surrounding area, while several homes line the opposite bank, contributing to the serene setting.

4.94 out of 5 average rating, 53 reviews

Excellent Location! Gulf Access, Heated Pool Chic!

4.88 out of 5 average rating, 8 reviews

Sunny Pool Retreat – 20 Minutes from the Beach!

Two wicker lounge chairs are positioned beside a private heated pool, framed by a screened lanai. A soft blue blanket is draped over one chair, while lush tropical greenery is visible through the screen, creating a serene outdoor space.

4.91 out of 5 average rating, 54 reviews

Spacious 4 BR Retreat w/ 3 Ensuites, Pool & Spa

4.93 out of 5 average rating, 97 reviews

Guesthouse in Estero

Adorable Estero Cottage - Heated Pool/Spa - Sauna

4.95 out of 5 average rating, 22 reviews

Gulf Waterfront Getaway-Pool•Dock•Grill•Games•Boat

4.96 out of 5 average rating, 94 reviews

A refreshing pool is showcased alongside a spa, surrounded by a secure mesh fence. Vibrant green trees frame the area, offering a natural backdrop. Two lounge chairs with pink stripes provide a relaxing seating option near the poolside.

Villa in Bonita Springs

New”Waterfront” Gulf Access 3/3 Villa pool heater

The exterior of a single-story home is displayed, featuring a light gray facade and a spacious driveway. Arched windows are prominently featured, providing an open and inviting look. A well-maintained lawn with minimal landscaping enhances the welcoming appearance, and a clear blue sky with scattered clouds is visible overhead.

4.95 out of 5 average rating, 21 reviews

Casa Cypress