
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.

Ft Myers Beach & Lovers Key State Park- FANTASTIC!
BEACHES ARE OPEN! Beautiful Views, large unit, Enjoy the sun, beach, and excitement of Florida. Lovers Key State Park, beautiful beaches, hiking & biking trails, Ft Myers Beach, white sand, many activities. Views of the gulf & bay area. Exercise room, wifi, great swimming pool- the beaches & trails you come to Florida for. Ft Myers beach has the white sand you think of when visiting Florida. The Gulf Coast Beach, and Lovers Key State Park are there for your enjoyment. Great place for Memories

Heated Pool | Canal | Modern | New | Southern Exp.
Welcome to the brand new, absolutely stunning, Villa Southbreeze! This 3 bedroom, 2 bathroom vacation rental is fully furnished &equipped. Stunning high ceilings, huge 72" fireplace, office, laundry room all Samsung stainless-steel appliances, and much more. Out by the huge screened-in pool area you'll find a private electric heated pool, BBQ propane grill, several loungers, large table + chairs. The heated pool features two fountains and a shallow "beach area". Welcome to the villa Southbreeze!

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.

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.

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.

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

Tropical Oasis: Stunning Pool Home in Bonita
Welcome to your tropical getaway in Bonita Springs! This stunning 4-bedroom, 2-bathroom home features a heated pool with a sunshelf, offering the perfect spot to soak up the Florida sunshine. Centrally located near the Coconut Point Mall, you'll have easy access to shopping, dining, and you're located just 15 minutes from Bonita Beach. Inside, enjoy spacious, coastal-themed living areas ideal for gatherings with family and friends. Your private oasis awaits—book now for a memorable stay!

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.

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.

675 FantaSea | New Heated Resort Pool & Fire Pit
Spend the day outside morning, noon & night and live out your FantaSea vacation! Lounge on the deck or in the heated pool on the sun shelf. On a cool night sit by the fire and relax in the Adirondack chairs. Desirable designer interior with coastal decor has the comfort of home with the feel of the sea. We are just a few minutes away from white sandy beaches with beautiful sunsets, amazing restaurants and upscale shopping centers.
Popular amenities for Estero rentals with a pool
House rentals with a pool

Private Palm Oasis - Close to Beach

Latitude Adjustment - With Pool & Outdoor Kitchen

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

Luxe Lakeside Living: Stunning Home w/ Pool & Spa

Stunning Beach Cottage!

Classic Arcades Heated Pool Home by Beach & Dining

Luxurious Poolside Paradise: 4100 SqFt 5BR Home

Bonita Beach Beauty
Apartment rentals with a pool

Oceanview Oasis on Bonita Beach Bld3 Floor5

Sally’s Seaside Escape – Walk to Beach + Views

Beachfront fully equipped apartment

Oceanview unit. Completely remodeled Pool is open!

Bonita Beach and Tennis 5807

Lush tropical 1st floor getaway in Naples

Bonita Beach and Tennis 3907 - Ocean Views

Easy Breezy Too
Other holiday rentals with a pool

Luxury Canalfront Pool Retreat w/ Upscale Finishes

Beachfront @ Elevate in the Sun!

Waterfront Condo with Pool & Boat Slip

Pool, Hot Tub, Kayaks, Dock & Canal w/ Gulf Access

Luxury II

Beachy Escape: 2BR/2BA w./ Pool, Gym, and Theater

Villa Bonita - Pool, Hot Tub, Fire Pit

Bonita Bungalow w/pool *Great Location*
When is the best time to visit Estero?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | ₹20,482 | ₹22,368 | ₹21,470 | ₹18,146 | ₹17,697 | ₹16,709 | ₹16,799 | ₹15,721 | ₹14,733 | ₹18,326 | ₹20,572 | ₹21,021 |
| 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 ₹3,593 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
- The Club at The Strand
- Clam Pass Park
- 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




