
Vacation rentals with a pool in Estero
Find and book unique homes with a pool on Airbnb
Quick stats about vacation rentals with a pool in Estero

Total vacation rentals
Explore 170 vacation rentals in Estero

Nightly prices starting at
Estero vacation rentals start at ﺩ.ﺇ 147 per night before taxes and fees

Verified guest reviews
Over 1,680 verified reviews to help you choose

Family-friendly vacation rentals
140 properties offer extra space & kid-friendly amenities

Pet-friendly vacation rentals
Find 40 rentals that welcome pets

Rentals with dedicated workspaces
90 properties have a dedicated workspace

Wi-Fi availability
160 of Estero vacation rentals include wi-fi access

Popular amenities for guests
Guests love Kitchen, Wifi, and Pool across Estero rentals

4.9 Average rating
Estero stays are highly rated by guests—averaging 4.9 out of 5!
Top-rated rentals with a pool in Estero
Guests agree: these homes with a pool are highly rated for location, cleanliness, and more.

McGregor’s Gem• Heated Pool 3BR/2BA River District
🌴 Welcome to McGregor’s Gem—your ideal Southwest Florida retreat! Dive into relaxation in your private heated pool, spread out across three bedrooms and two baths, and enjoy the perfect blend of peaceful tree-lined neighborhood living just minutes from the charming Downtown Fort Myers River District, world-class beaches, and top local attractions.☀️ Whether you’re traveling with family, friends, or on business, this home offers all the modern comforts you need for a relaxing, stress-free stay

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!

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.

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.

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.

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!

*Relaxing and Fun Pyramid Home in Ft Myers (7048)
Get ready for a unique vacation in a fully equipped pyramid home!! Enjoy exploring all of southwest Florida and then return home where you can relax on your own private patio or jump in the natural spring water lake! Located in south Ft Myers, easy distance to most attractions, 15 miles to beaches!! -Free WIFI -washer dryer -full kitchen -2 patios with dining area -self check in with lock box -perfect for families, great friends, couples -Beach gear provided -2 bedrooms/ 1 bathroom unit

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

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.

Beautiful 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.

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.

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.
Popular amenities for Estero rentals with a pool
House rentals with a pool

Modern Coastal Retreat / heated pool and hot tub

Luxury Pool Home - South Fort Myers

Beautiful private getaway in Bonita Springs

Upscale Family Haven. Heated Spa and Pool

Newly Renovated Home Just Minutes From The Beach!

Heated Pool Home Near Beaches, Airport & Shopping

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

Excellent Location! Gulf Access, Heated Pool Chic!
Condo rentals with a pool

Rare walkout condo on Sanibel beach

Bonita Beach and Tennis 1903

Beachfront fully equipped apartment

Ft Myers Beach & Lovers Key State Park- FANTASTIC!

Lover's Key Resort Unit #807

The Sunset @ Naples Boutique | Walk 2 Beaches

View of Gulf, Steps to Beach@The Turquoise Turtle

Amazing Condo-1 mile from Bonita Beach
Other vacation rentals with a pool

Adorable Estero Cottage - Heated Pool/Spa - Sauna

Latitude Adjustment - With Pool & Outdoor Kitchen

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

Swimsational Golf views

Gulf Access/Heated Pool & Jacuzzi/Up to 8

Sunny, open 3 BR, 2 BA *pool* home

Resort-Style Pool | Tropical Oasis | Pet-Friendly

3BD Oasis w/Private Pool • 1 Acre • Near Beaches
When is the best time to visit Estero?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | ﺩ.ﺇ 804 | ﺩ.ﺇ 918 | ﺩ.ﺇ 845 | ﺩ.ﺇ 845 | ﺩ.ﺇ 643 | ﺩ.ﺇ 628 | ﺩ.ﺇ 687 | ﺩ.ﺇ 643 | ﺩ.ﺇ 602 | ﺩ.ﺇ 643 | ﺩ.ﺇ 690 | ﺩ.ﺇ 746 |
| Avg. temp | 18°C | 20°C | 21°C | 24°C | 26°C | 28°C | 29°C | 29°C | 28°C | 26°C | 23°C | 20°C |
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- Naples Beach
- Captiva Island
- Englewood Beach
- Lovers Key Beach
- Tigertail Beach
- Florida Gulf Coast University
- Stump Pass Beach State Park
- Bowman's Beach
- Montura Ranch Estates
- Barefoot beach Bonita Springs,FL
- Jetblue Park
- Bonita National Golf & Country Club
- Boca Grande Pass
- The Naples Pier
- Yacht Club Public Beach
- Edison & Ford Winter Estates
- Ave Maria University
- Bunche Beach
- Coconut Point
- Clam Pass Park
- Delnor-Wiggins Pass State Park
- Lovers Key State Park
- Barefoot Beach State Preserve
- Coral Oaks Golf Course





