
Holiday 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.

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.

Golf & Pool Views! Close to FGCU and Airport.
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.

Central 3BD/2BA •Massive Heated Pool •Golf courses
🌞 Gorgeous Heated Pool Home Near Everything – Perfect for a Relaxing & Convenient Getaway! Welcome to your tropical escape in the heart of SW Florida! This beautifully maintained 3BD/2BA home is located just minutes from world-class beaches, and top local attractions, offering the perfect blend of tranquility, comfort, and accessibility. Whether you're here for a family vacation, a romantic getaway, or a business trip, this home provides everything you need for a restful and memorable stay.

Ken & Gina's Beach Condo (#2301)
Due to hurricane Ian, the courtyards and tennis courts are under repair. Pools are open. 2 of 4 entrances are open. Studio condo across the street from Bonita Beach. 3rd floor unit offering partial views of the gulf. Being able to walk to the beach (2 mins) and 2 restaurants while centrally located between Ft. Myers and Naples makes this a great location. Local bike rental shops offer delivery of bicycles. Bonita beach offers jet ski, paddle board and catamaran rental. Parking is free

Comfy 3 BR-Group Friendly-Pool Access-BBQ-FGCU
Everything your group needs to be comfortable. 2 car garage w/remote Plenty of FREE on-site driveway parking for large work vehicles Logo vehicles ok Screened lanai w/ seating & BBQ Washer/Dryer Free, secure WiFi Smart TV in all rooms & 65” TV in Living Room Electric fireplace Well-stocked kitchen Keurig & Drip coffeemaker Toaster/crockpot Soap (laundry, dish, body, hair) Bathroom Items (Hair dryer, flat iron) Pantry items Community Pool Access 1 mile-Low fee Pack & Play & baby bath support

*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

Pool Bikes & Beach | Paddle Board Included
We welcome your family of up to 2 adults & 3 children. You will be close to sandy beaches, great restaurants and shopping at this great North Naples Location. Just a few minutes from Vanderbilt Beach and Wiggins Pass Park. You will love all the great amenities and be able to relax in this brand new clean apartment. Amenities, Bikes, paddle board, beach wagon and beach towels. Very easy to check-in, you will have your own private entrance and private one car parking available.

Bonita Beach and Tennis 5807
Steps away from beautiful Bonita Beach is our studio condo equipped with everything you need for the prefect beach getaway. Lanai with incredible views of evening sunsets. Gulf views from lanai, living room and bedroom. Walk-in shower, plenty of storage space. Fully equipped kitchen, linens, cooler, beach chairs and towels. 2 heated pools on site. 2 fun restaurants, both on the water, within walking distance. DUE TO HURRICANES IAN & MILTON SOME WORKERS ARE STILL ON SITE.

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.

Luxury Cape Coral Villa with Private Heated Pool
Escape to your own private pool oasis in sunny Southwest Florida—where swaying palms, crystal-clear water, and warm coastal breezes set the stage for relaxation, family fun, and unforgettable memories. Hassle-Free Stay: NO CHECKOUT DUTIES – just enjoy your stay! IMPORTANT: Please ensure you've read and accept the house rules prior to booking. Thank you. Easy access to Fort Myers (RSW) and Punta Gorda (PGD) Airports – only 24 miles away!

Cozy studio 1.3 miles to Barefoot Beach
Very inexpensive way to get close to the beach and still have complete privacy! Whole unit-Share nothing. Small and cozy studio/room 12x19 with a refrigerator, microwave, air conditioner, full bath, suitable to more or less sleep. Queen size bed. Closet and dresser. This is a separate guest room with a private entrance not connected to another unit. Located in an adorable tropical feel complex in a seafoam green building.

3BR w/HUGE 2k sq ft Lanai & Seasonally Heated Pool
Welcome to our peaceful Bonita Springs vacation retreat! This isn't just a rental, this is our home and we treat it as such: - You won't experience clean, you will experience immaculate. - You won't experience adequate, you will experience exceptional!. Come see for yourself...and you will be back year after year! Perfectly located between Naples, Fort Myers, numerous beaches & amazing shopping at every turn!
Popular amenities for Estero rentals with a pool
House rentals with a pool

Lovely Beach Bungalow pool/spa 1.5 mile bch Naples

Cathedral Heights

Paradise on Estero Bay

Luxe Unique: Close to Beach, Hot Tub, Heated Pool

The Trellis House With Sauna (Pool not Heated)

Coastal Modern Retreat with Heated Pool and Spa

Dive into Luxury: Stunning Tropical Home & Pool

Experience of a lifetime
Apartment rentals with a pool

Cozy Coastal Escape. Close to FMB and Sanibel

Bonita Beach and Tennis 1903

Gulf Water Views + 2 bikes, beach gear weekly stay

Ft Myers Beach & Lovers Key State Park- FANTASTIC!

Oceanview unit. Completely remodeled Pool is open!

Lush tropical 1st floor getaway in Naples

Beach condo-Naples/Bonita Springs

Park Shore Resort Modern Top Floor 2 Bed 2 Bath
Other holiday rentals with a pool

Bonita Bay 2 Bed 2 Bath with Beach Shuttle Access

Waterfront Condo with Pool & Boat Slip

Calypso Cottage with Boat Access. Sleeps 8

Villa Bonita - Pool, Hot Tub, Fire Pit

Seabreeze Hideaway

Beach Cottage

Paradise Found

Walk to Downtown / 10 min to Beach / Cable TV
When is the best time to visit Estero?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | € 196 | € 214 | € 205 | € 174 | € 169 | € 160 | € 161 | € 150 | € 141 | € 175 | € 197 | € 201 |
| 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 holiday rentals with a pool in Estero

Total holiday rentals
Explore 160 holiday rentals in Estero

Nightly prices starting at
Estero holiday rentals start at € 34 per night before taxes and fees

Verified guest reviews
Over 1,270 verified reviews to help you choose

Family-friendly holiday rentals
130 properties offer extra space & child-friendly amenities

Pet-friendly holiday rentals
Find 30 rentals that welcome pets

Rentals with dedicated workspaces
80 properties have a dedicated workspace

Wifi availability
160 of Estero holiday 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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- Rentals with pools Lee County
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- Rentals with pools United States
- Naples Beach
- Captiva Island
- Lovers Key Beach
- Barefoot beach Bonita Springs,FL
- Englewood Beach
- Clam Pass Park
- The Club at The Strand
- Stump Pass Beach State Park
- Bonita National Golf & Country Club
- Tigertail Beach
- Heritage Bay Golf & Country Club
- LaPlaya Golf Club
- Morgan Beach
- Cypress Woods Golf & Country Club
- Spanish Wells Country Club
- Seagate Beach Club
- The National Golf & Country Club Ave Maria
- Panther Run Golf Club
- The Quarry Golf Club Naples
- Boca Grande Pass
- Worthington Country Club
- Esplanade Golf & Country Club of Naples
- Park Shore Beach Park
- Sanibel Island Northern Beach




