
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.

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.

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

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

Luxe Unique: Close to Beach, Hot Tub, Heated Pool
Step into the luxurious 2BR 2BA oasis in the heart of Bonita Springs, FL. It promises a relaxing retreat just a few minutes from the pristine Bonita Beach, restaurants, shops, exciting attractions, and natural landmarks. The stylish design and a rich amenity list will leave you in awe. ✔ 2 Comfortable Bedrooms ✔ Open Design Living ✔ Fully Equipped Kitchen ✔ Backyard (Pool, Hot Tub, Swim-Up Bar, BBQ) ✔ Lounge Pool House ✔ Workspace ✔ Smart TVs ✔ Wi-Fi ✔ Parking See more below!

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.

2 Kings, Pool, Gulf Canal, Game Room and Kayaks
Unwind Cape Coral welcomes you to sunny southwest Florida, close to magnificent beaches, fishing, shelling, Minnesota Twins Spring Training & much more. Come enjoy this new construction home with heated pool, Kayaks, heated and cooled game room (PlayStation 5), gulf access - salt water canal, 4k oled tv's & many more refreshing amenities. You will love this clean & bright home with lovely décor. Located in the highly sought after Pelican neighborhood of Southwest Cape Coral!

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 Beach and Tennis 3907 - Ocean Views
Welcome to our beautiful condo. We are located on the 9th Floor of Bldg. 3 at Beach and Tennis Club. Beautiful sunsets await you in our 1-bedroom,1 bath, studio condo with views galore of the Gulf. We are just a short walk from the beach and restaurants. Come and enjoy the sunsets from our private balcony. Amenities such as shared pools and private balcony are all open and available for use to relax & unwind while listening to the soothing sounds of waves.

Lovers Key Beach Club Suite - Private Beach
Enjoy breathtaking views from this 10th floor condo at Lover's Key Beach Club! This one bedroom, one bath condo is the perfect place for a quiet, romantic couples getaway. From the private beach to the large pool area, there's no better place to relax in the Florida sunshine! Wake up refreshed and sip your coffee on the private balcony overlooking the water. Prepare meals in the full kitchen or head down to the BBQ grill area!

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.

Gulf Water Views + 2 bikes, beach gear weekly stay
Beachfront & Gulf Water Views at Estero Beach & Tennis Club 206C Wake up to unobstructed Gulf views in this 5-star Fort Myers Beach condo! Enjoy early check-in, no checkout chores, and every comfort—from a king GhostBed, full kitchen with dishwasher, free high-speed WiFi, heated pool, tennis/pickleball courts, BBQ grills, free parking, and stocked beach gear. Steps from the sand with sunsets you’ll never forget.
Popular amenities for Estero rentals with a pool
House rentals with a pool

Modern Coastal Retreat / heated pool and hot tub

Lovely Beach Bungalow pool/spa 1.5 mile bch Naples

The Trellis House With Sauna (Pool not Heated)

Villa Bonita - Pool, Hot Tub, Fire Pit

Coastal Modern Retreat with Heated Pool and Spa

*Relaxing and Fun Pyramid Home in Ft Myers (7048)

Newly Renovated Home Just Minutes From The Beach!

Central 3BD/2BA •Massive Heated Pool •Golf courses
Apartment rentals with a pool

Oceanview Oasis on Bonita Beach Bld3 Floor5

Boutique condo on the bay, short walk to the beach

Ft Myers Beach & Lovers Key State Park- FANTASTIC!

Beautiful 8th Floor Gulf View Condo

Oceanview unit. Completely remodeled pool is open!

Cozy Condo with amazing views, next to beach

Park Shore Resort Modern Top Floor 2 Bed 2 Bath

Luxury Condo by Cape Harbor and Excellent Dining!
Other holiday rentals with a pool

Private Spa Oasis: 5 min Beach/Heated Pool/Firepit

Luxury Modern Coastal Home w/ Pool & Game Room

3BD Retreat | New Heated Pool | Close to Beaches

Grace by The Sea · 2025 Build · Steps to Beach

Explore close summer beaches. Cozy, clean, fun!

Executive King Suite City View | Downtown Ft Myers

Private Heated Pool Paradise Getaway

6min to Beach·Heated Pool·Pet Friendly
When is the best time to visit Estero?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | ₹20,891 | ₹22,815 | ₹21,899 | ₹18,509 | ₹18,051 | ₹17,043 | ₹17,134 | ₹16,035 | ₹15,027 | ₹18,692 | ₹20,983 | ₹21,441 |
| 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 180 holiday rentals in Estero

Nightly prices starting at
Estero holiday rentals start at ₹5,498 per night before taxes and fees

Verified guest reviews
Over 1,410 verified reviews to help you choose

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

Pet-friendly holiday rentals
Find 30 rentals that welcome pets

Rentals with dedicated workspaces
90 properties have a dedicated workspace

Wifi availability
170 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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- Naples Beach
- Captiva Island
- Lovers Key Beach
- Marco Island Public Beach Access
- Englewood Beach
- Clam Pass Park
- Stump Pass Beach State Park
- Tigertail Beach
- Heritage Bay Golf & Country Club
- Bonita National Golf & Country Club
- Esplanade Golf & Country Club of Naples
- Boca Grande Pass
- Bunche Beach
- Edison & Ford Winter Estates
- Del Tura Golf & Country Club
- Talis Park Golf Club
- Delnor-Wiggins Pass State Park
- Stonebridge Country Club
- Manatee Park
- Coral Oaks Golf Course
- Bonita Beach Dog Park
- Sun Splash Family Waterpark
- Four Mile Cove Ecological Preserve
- Coconut Point




