
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.

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!
5.0 out of 5 average rating, 101 reviews
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!
4.99 out of 5 average rating, 264 reviews
100+ 5 Star Reviews and Right on The Beach!
We are a Superhost for a reason! Sanibel Siesta looks amazing! Immaculate beachfront, 2BR, 2BA w/garage, nicely updated beachy unit at sand's edge. Cooks kitchen. Amazing views of the Gulf w/5 star ratings! 3-day min. New hurricane windows, nicely furnished with ELEVATOR IN BUILDING! Discount for weekly/mo. rentals. BR 1:King bed ensuite, smart TV. BR 2: 2 tw. beds, smart TV. Qn. sofa bed in LR. Pool, golf course, bikes, laundry on site. No food or condiments stored in unit. May allow sm. dog.
4.95 out of 5 average rating, 121 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.
4.94 out of 5 average rating, 163 reviews
"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.
4.99 out of 5 average rating, 106 reviews
Beach, Hot Tub & htd pool. 2 Owner Suites w 2 King
The perfect Naples beach getaway for families and/or groups of 8–10 and just a few minute bike ride to the beach. The home doesn't just sleep large groups, it supports it with every space designed for guests to gather. Bikes and beach gear are included, plus guest-only perks including local beach know-how, golf cart rental and shuttle options, pre-arrival fridge stocking, Naples recommendations, and special benefits with select local partners. Less time planning. More time enjoying Naples.
4.96 out of 5 average rating, 139 reviews
Family Oasis with Heated Pool & Spa Near Beaches
Step into your dream vacation at our 3-bedroom retreat in Bonita Springs. With two king beds, a queen and twin, plus a pull-out couch, this house is perfect for up to 9 guests. Dive into the heated pool and hot tub after a day at stunning Bonita Beach, Barefoot Beach,& Wiggins Pass - just 2 miles away and a short drive. Explore nearby mini-golf, diverse dining options & the allure of Naples shopping. Focus on children amenities & updated premium linens at this pristine oasis!
4.99 out of 5 average rating, 108 reviews
Palm Paradise Retreat | Pool Oasis
Welcome to your private Southwest Florida retreat. This beautifully appointed 4-bedroom, 2-bathroom home features a screened-in pool, outdoor kitchen, covered lanai, and spacious indoor-outdoor living areas designed for relaxation and entertaining. Whether you're enjoying a day by the pool, grilling dinner outdoors, or exploring the area's beaches, shopping, and dining, this home offers the perfect setting for a memorable Florida getaway with family and friends.
5.0 out of 5 average rating, 8 reviews
Cozy 2 bedroom on the canal with pool and hot tub!
Welcome to your relaxing retreat in beautiful Bonita Springs, Florida. This comfortable home is located in a quiet neighborhood, offering a peaceful stay with easy access to everything Southwest Florida has to offer. Perfect for families, couples, or business travelers. You’re just a short drive from Bonita Beach, Barefoot Beach, Coconut Point shopping, and great local dining. Enjoy nearby boating, fishing, golf, and nature preserves, all within minutes.
4.76 out of 5 average rating, 17 reviews
Dolphin beach house 2
ONE OF THE BEST WATERFRONTS IN CAPE CORAL! A short walk to the beach . This 2,500+sq ft home has stunning sunsets and South Western water views from all main living areas,as well as the Master Suite. Heated pool w/ LED colored lighting, built in Spa,Pool bath, full laundry facility, Lanai,Fireplace ,Wi-fi and TVs in every bedroom, private dock . Boat on lift for rent w/RPM rentals . Large 2-car garage w/5 bicycles,beach wagon & cooler on site.
4.97 out of 5 average rating, 326 reviews
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
4.81 out of 5 average rating, 185 reviews
Modern Coastal Retreat / heated pool and hot tub
Newly furnished, spacious retreat. This home built in 2019, has a modern, comfortable feel. Relax and swim in the heated pool and hot tub. High speed internet and TV are available in each room. The whole group will enjoy easy access to everything from this centrally located home. Close to Coconut Point, Hyatt Regency Coconut Point and Estero Bay. 10 minute drive to Miramar Outlets and 20 minutes to Naples / 5th Ave.
5.0 out of 5 average rating, 86 reviewsPopular amenities for Estero Bay rentals with a pool
House rentals with a pool

Bonita Retreat: Heated Pool - Minutes to Beach
4.99 out of 5 average rating, 150 reviews
3BR w/HUGE 2k sq ft Lanai & Seasonally Heated Pool
4.98 out of 5 average rating, 130 reviews
Whole cozy house
4.95 out of 5 average rating, 405 reviews
Classic Arcades Heated Pool Home by Beach & Dining
4.95 out of 5 average rating, 115 reviews
Luxury Canal Oasis | Pool + Spa + Walk to Beach
4.96 out of 5 average rating, 117 reviews
Modern Oasis Estero Bay
5.0 out of 5 average rating, 35 reviews
Barefoot Breeze 2
5.0 out of 5 average rating, 46 reviews
Modern Coastal Home w/ Pool & Game Room
5.0 out of 5 average rating, 54 reviewsCondo rentals with a pool

Amazing Condo-1 mile from Bonita Beach
4.95 out of 5 average rating, 153 reviews
Rare walkout condo on Sanibel beach
4.9 out of 5 average rating, 263 reviews
Easy Breezy.
4.91 out of 5 average rating, 164 reviews
Casa Bonita - Relax @ The Beach (Newly Remodeled)
4.99 out of 5 average rating, 179 reviews
The Sunset @ Naples Boutique | Walk 2 Beaches
4.96 out of 5 average rating, 106 reviews
Ken & Gina's Beach Condo (#2301)
4.92 out of 5 average rating, 151 reviews
Bonita Beach and Tennis 3907 - Ocean Views
4.97 out of 5 average rating, 159 reviews
Fort Myers Beachfront Escape - Walk to the Sand!
5.0 out of 5 average rating, 17 reviewsOther vacation rentals with a pool

Bonita Beach Direct Beach Front Luxury & FUN
4.88 out of 5 average rating, 16 reviews
Private Palm Oasis - Close to Beach
5.0 out of 5 average rating, 71 reviews
Luxury Waterfront Home • Pool • Dock • Near Beach
5.0 out of 5 average rating, 33 reviews
Chic Naples Coastal Retreat – Heated Pool and Spa
4.94 out of 5 average rating, 17 reviews
4-BR Family Home • Pool • Beach Access Across Stre
4.92 out of 5 average rating, 12 reviews
Upscale Family Haven. Heated Spa and Pool
5.0 out of 5 average rating, 15 reviews
Luxury Beachside House W/ Heated Pool & Elevator
5.0 out of 5 average rating, 68 reviews
Fort Myers Beach | private pool | bikes | Arcade
4.91 out of 5 average rating, 54 reviewsDestinations to explore
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- Naples Beach
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- Lovers Key Beach
- Florida Gulf Coast University
- Tigertail Beach
- Bowman's Beach
- Stump Pass Beach State Park
- Montura Ranch Estates
- Jetblue Park
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- Bonita National Golf & Country Club
- The Naples Pier
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- Clam Pass Park
- Bunche Beach
- Delnor-Wiggins Pass State Park
- Barefoot Beach State Preserve
- Lovers Key State Park
- Coral Oaks Golf Course





