
Vacation rentals with a pool in Estero
Find and book unique homes with a pool on Airbnb
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.

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

Renaissance Oasis Retreat
Welcome to a unique, stylish modern home where families can create lasting memories. Dive into the private pool or gather around the barbecue grill for unforgettable outdoor meals with loved ones. Located just minutes from Bonita Beach and the popular Coconut Point Mall, enjoy the perfect mix of relaxation and convenience with easy access to top-notch restaurants, shopping, and entertainment. This beautiful home offers the ultimate setting for both family fun and peaceful retreats.

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.

Private pyramid home to relax and explore-7021
Relax and enjoy the beauty of sunny southwest Florida in your own unique pyramid! This private vacation home in Pyramid Village features a spring water lake just a short walk from your pyramid (this pyramid has nature views, not lakeside) *Home includes: Free WIFI, private patio with gas grill, washer/dryer, fully equipped kitchen, and 2 queen beds (comfy for 4 guests), 2 Roku TV's, and beach gear (located 15 miles from most popular beaches). * self check in with lock box

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.

Family Oasis | Heated Pool + Beach Gear, Kid Ready
Escape to this stylish, family-friendly 4-bedroom, 3-bath retreat with a heated pool and sunshelf, perfect for soaking up the Florida sunshine. Located minutes from Coconut Point Mall, the Hyatt Regency Coconut Point, and a short drive to Bonita Beach, you’ll have the best of shopping, dining, and the coast at your fingertips. Inside, boho-inspired spaces provide plenty of room to relax, gather, and create lasting memories. Your private getaway awaits, book today!
Popular amenities for Estero rentals with a pool
House rentals with a pool

Luxury Heated Pool Home-Minutes to Barefoot Beach

Gulf Access Canal Home with Seasonally Heated Pool

Gulf Access/Heated Pool & Jacuzzi/Up to 8

Modern Coastal Retreat / heated pool and hot tub

Luxury Pool Home - South Fort Myers

Luxury Modern Coastal Home w/ Pool & Game Room

Luxurious 4-Bed Pool Home with Dock & Gulf Views,

The Trellis House With Sauna (Pool not Heated)
Condo rentals with a pool

Bonita Beach and Tennis 1903

Beachfront fully equipped apartment

Ft Myers Beach & Lovers Key State Park- FANTASTIC!

Oceanview unit. Completely remodeled pool is open!

2nd Floor Beachfront Condo Sanibel Harbour

Lovers Key Beach Club Private Beach

100+ 5 Star Reviews and Right on The Beach!

Casa Bonita - Relax @ The Beach (Newly Remodeled)
Other vacation rentals with a pool

Adorable Estero Cottage - Heated Pool/Spa - Sauna

Anchor's Away Beach Home & Guest Pool House

Latitude Adjustment - With Pool & Outdoor Kitchen

Bright Bonita Springs Pool Home Near Gulf Beaches

Swimsational Golf views

Turtle Cove Relaxing Getaway Pool + Resort vibe

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

Family, friendly Tropical Oasis with Heated Pool.
When is the best time to visit Estero?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $310 CAD | $354 CAD | $326 CAD | $286 CAD | $279 CAD | $263 CAD | $265 CAD | $248 CAD | $232 CAD | $248 CAD | $266 CAD | $287 CAD |
| 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 |
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 $71 CAD per night before taxes and fees

Verified guest reviews
Over 1,490 verified reviews to help you choose

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

Pet-friendly vacation rentals
Find 30 rentals that welcome pets

Rentals with dedicated workspaces
80 properties have a dedicated workspace

Wifi availability
160 of Estero vacation rentals include wifi 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!
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- Naples Beach
- Captiva Island
- Englewood Beach
- Lovers Key Beach
- Tigertail Beach
- Florida Gulf Coast University
- Stump Pass Beach State Park
- Bonita National Golf & Country Club
- Bowman's Beach
- Barefoot beach Bonita Springs,FL
- Boca Grande Pass
- Jetblue Park
- Montura Ranch Estates
- The Naples Pier
- Clam Pass Park
- Bunche Beach
- Edison & Ford Winter Estates
- Yacht Club Public Beach
- Ave Maria University
- Coral Oaks Golf Course
- Delnor-Wiggins Pass State Park
- Lovers Key State Park
- Coconut Point
- Barefoot Beach State Preserve





