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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.

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Guest favourite
The exterior of the condo complex is shown, featuring a sign that reads 'Casa Bella.' Lush green landscaping surrounds the building, with palm trees and neatly trimmed bushes. Two-story units are visible, highlighting a calm and inviting atmosphere under a clear blue sky.
Apartment in Fort Myers
4.91 out of 5 average rating, 180 reviews

Ft. Myers Quaint Getaway! Minutes from Beach!

My condo is close to the beach, NOT on the beach, nightlife, public transport, and family-friendly activities. It is good for couples, solo adventurers, business travelers, and families (with kids). It's minutes from Ft. Myers and Sanibel Beach. It has a King size bed in the master bedroom and two twin murphy beds in the guest room. Walking distance from a Super Target. Several outlet malls, closest is 2 miles. FYI, not handicap accessible (second floor unit). A few steps to the pool and grill.

Top guest favourite
A clean outdoor pool is surrounded by a safety fence, with clear blue water reflecting the sky. Several lounge chairs are positioned nearby for relaxation, while lush greenery and an open landscape are visible in the background, creating a serene atmosphere.
Flat in Fort Myers
4.94 out of 5 average rating, 112 reviews

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.

Guest favourite
Home in Bonita Springs
5 out of 5 average rating, 12 reviews

Estero Bay Modern Oasis

Welcome to Modern Oasis Estero Bay - a serene retreat designed to give you the ultimate vacation experience! This beautiful home has 4 bedrooms plus a bunk room, 2 bathrooms, and a great room overlooking the backyard oasis. Relax & unwind in the heated salt water pool & hot tub, grill & dine in the covered patio and enjoy the sunset views over Estero Bay. The home backs onto a golf course and is minutes to shops & restaurants at Coconut Point, and a short drive to the beautiful Barefoot Beach.

Top guest favourite
A serene pool area is featured, surrounded by lush tropical greenery. A large umbrella provides shade over two white lounge chairs positioned beside the pool. A covered seating area is visible in the background, adding to the outdoor relaxation space.
Home in Fort Myers
4.88 out of 5 average rating, 24 reviews

The Trellis House With Sauna (Pool not Heated)

Welcome to our charming home located just 5 minutes from RSW airport and close to major shopping centers and restaurants, making it an ideal spot for both business and leisure travelers. Enjoy a quick 15-minute drive to the beach, where you can unwind and soak up the sun. For those visiting for work, the Amazon headquarters is just a short distance away. Whether you're here for a quick getaway or a longer stay, our location offers comfort, convenience, and easy access to everything you need.

Top guest favourite
Home in Fort Myers
4.99 out of 5 average rating, 101 reviews

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 TVs in bedrooms & Living Room Full size appliances & well-stocked kitchen Keurig & Drip coffeemaker Toaster/crockpot Soap (laundry, dish, body, shampoo/conditioner) Bathroom Items (Hair dryer, flat iron) Pantry items Community Pool Access 1 mile-Low fee New Pack & Play

Guest favourite
Home in Bonita Springs
5 out of 5 average rating, 8 reviews

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!

Guest favourite
Guest house in Estero
4.93 out of 5 average rating, 68 reviews

Adorable Cottage with Heated Pool -Jaccuzi - Sauna

Come and relax in this calm, stylish space located one acre property full of pines and fruit trees, with access to the House Heated Pool with Jacuzzi and the sauna. Modern design will make you feel comfortable. Close to Bonita, Ft.Myers, Lovers key and Sanibel beaches & fishing piers. Cottage is 12 miles away (19 km) from RSW airport, about 20 min of driving. We are happy to meet our guests, but also respect your privacy. Your comfort is our priority.

Top guest favourite
Home in Naples Park
4.98 out of 5 average rating, 133 reviews

Walk to Vanderbilt Beach, Pets, 2 Mstrs w Kings

Fabulous 500 block location. Just a short walk/bike ride to the beach. This exclusive layout w 2 master suites, large walk-in closets, and private baths. Every living space has been thoughtfully designed for large groups of 8-10 to gather and enjoy. The house is fully stocked. This includes a coffee maker, dishes, pots and pans, beach cruiser bikes, beach chairs, a wagon, etc. All you need is to pack your bags, sit back and relax...

Top guest favourite
A cozy sleeping area features a queen size bed dressed in a nautical-themed quilt. A small refrigerator and microwave are visible, along with a dresser and television. Light enters through a shuttered window, complementing the soft blue walls.
Apartment in Bonita Springs
4.82 out of 5 average rating, 220 reviews

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.

Guest favourite
Home in Fort Myers
4.9 out of 5 average rating, 161 reviews

Dive into Luxury: Stunning Tropical Home & Pool

Escape to a tropical paradise in this stunning 1952 midcentury modern home, perfectly located in the heart of historical McGregor Boulevard - home to the famous palm trees planted by Thomas Edison. Indulge in delicious meals at local restaurants like McGregor Cafe and McGregor Pizza, or tee off at the nearby public golf course. And if you're looking to hit the beach or explore downtown, both are just a short drive away.

Top guest favourite
A screened patio overlooks a serene swimming pool surrounded by lush greenery. Two lounge chairs are positioned nearby, with a small table featuring colorful drinks. A few inflatable toys float in the water, offering a casual ambiance for relaxation.
Home in Bonita Springs
4.97 out of 5 average rating, 114 reviews

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!

Top guest favourite
A serene outdoor space features elegant seating with plush cushions and wooden tables, set against the backdrop of a softly illuminated pool. The area is accented by vibrant blue drapes and warm lighting, creating a calm atmosphere for relaxation.
Home in Bonita Springs
4.97 out of 5 average rating, 160 reviews

Imperial Garden Riverside Retreat

Escape to paradise in our charming 3BR, 2BA home with a cozy den and extra bed. Enjoy privacy and seclusion in the tropical garden with a fire pit. Relax in the saltwater pool or unwind in the hot tub. With river access and paddleboards provided, adventure awaits. Fire up the gas grill for a delightful cookout. Ideal for families or friends seeking a serene, private retreat with all the comforts of home.

Popular amenities for Estero rentals with a pool

When is the best time to visit Estero?

MonthJanFebMarAprMayJunJulAugSepOctNovDec
Avg. price$298 SGD$325 SGD$312 SGD$264 SGD$257 SGD$243 SGD$244 SGD$229 SGD$214 SGD$267 SGD$299 SGD$306 SGD
Avg. temp18°C20°C21°C24°C26°C28°C29°C29°C28°C26°C23°C20°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 $52 SGD 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!

Destinations to explore

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  3. Florida
  4. Lee County
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