
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.

Magical Gateway in Naples FL
You'll fall in love with this tinny but magical place in the heart of Naples, modern open concept,high end finishes, a lot light, 2 BR queens beds, fine blinens, full bathroom with marble, enclosed pool, spacious back yard and a wood burning fire pit, 2 parking spaces just few steps from your front door. This place is near to all Naples has to offer, beautiful beaches, dining & nightlife, it is only 3km from the beach, 3 km from 5th ave in Old Naples and less than a mile from shopping centers.

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.

Lovely Beach Bungalow pool/spa 1.5 mile bch Naples
Lovely Pool/Spa bungalow, located in Naples Park, 1.5 miles from Vanderbilt Beach. Across the street from Marcato shopping center, Whole Foods, Cinema, restaurants and clubs. The unit is in pristine shape and features elegant furnishings and decor, tile floors throughout, granite counters in the kitchen, stainless steel appliances, impact windows and all white linens. Private screened in patio at the front and shared backyard area with pool/spa and BBQ. King Bed and Queen Sleeper Sofa.

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.

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!

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.

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.

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.

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

Private Palm Oasis - Close to Beach

Luxury Canal villa | Heated Pool | Covered Lanai

675 FantaSea | New Heated Resort Pool & Fire Pit

The Dolphin Villa Cape Coral Pool Home Sleeps 8

Boa Casa Bonita in SW Florida

2 Kings, Pool, Gulf Canal, Game Room and Kayaks

Renovated Pool Home in Historic Bonita Springs

Luxurious Naples Home. Heated Pool. Mins to Beach.
Condo rentals with a pool

Beachfront condo on 10 acres of pristine beach.

Boutique condo on the bay, short walk to the beach

Lovers Key Resort, Fort Myers Beach - Awesome

Quiet Coastal Haven by Barefoot Beach & Lakes

Luxury Condo by Cape Harbor and Excellent Dining!

Bonita Beach and Tennis 3907 - Ocean Views

Casa Bonita - Relax @ The Beach (Newly Remodeled)

Easy Breezy.
Other vacation rentals with a pool

Beachfront Beauty

Tropical Dream 2BR/2BA w./ Pool, Gym, and Theater

New Gorgeous Smart Home with Heated Pool on the Ca

Lehigh Eden| Pool & Jacuzzi | Games | Pet friendly

BRIGHT, AIRY, AND SPACIOUS 3 BD/2.5 BATH IN SWFL

Bonita Bungalow w/pool *Great Location*

Private Paradise Getaway

Luxury Beach Condo On The Bay In A tropical Oasis!
When is the best time to visit Estero?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec | 
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | ﺩ.ﺇ837 | ﺩ.ﺇ914 | ﺩ.ﺇ878 | ﺩ.ﺇ742 | ﺩ.ﺇ723 | ﺩ.ﺇ683 | ﺩ.ﺇ723 | ﺩ.ﺇ657 | ﺩ.ﺇ602 | ﺩ.ﺇ749 | ﺩ.ﺇ841 | ﺩ.ﺇ859 | 
| 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 160 vacation rentals in Estero 
 - Nightly prices starting at- Estero vacation rentals start at ﺩ.ﺇ147 per night before taxes and fees 
 - Verified guest reviews- Over 1,270 verified reviews to help you choose 
 - Family-friendly vacation rentals- 130 properties offer extra space & kid-friendly amenities 
 - Pet-friendly vacation rentals- Find 30 rentals that welcome pets 
 - Rentals with dedicated workspaces- 80 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! 
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- Naples Beach
- Captiva Island
- Lovers Key Beach
- Barefoot beach Bonita Springs,FL
- Englewood Beach
- The Club at The Strand
- Clam Pass Park
- Tigertail Beach
- Heritage Bay Golf & Country Club
- Bonita National Golf & Country Club
- Panther Run Golf Club
- LaPlaya Golf Club
- Morgan Beach
- Worthington Country Club
- Seagate Beach Club
- Spanish Wells Country Club
- The Quarry Golf Club Naples
- Stump Pass Beach State Park
- Boca Grande Pass
- Cypress Woods Golf & Country Club
- The National Golf & Country Club Ave Maria
- Sanibel Island Northern Beach
- Gasparilla Island State Park
- Esplanade Golf & Country Club of Naples
