Holiday rentals with a pool in Estero Island

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Top-rated rentals with a pool in Estero Island

Guests agree: these homes with a pool are highly rated for location, cleanliness and more.

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Top guest favourite

Home in Cape Coral

4.98 out of 5 average rating, 128 reviews

Heated Pool | Pet-friendly | Near Beach | Stocked

Catch your beach vibes at this newly renovated airy oasis with water views, relaxing lanai and huge heated pool in Cape Coral's desired Yacht Club community! Our coastal escape is pet and family friendly and is fully stocked with everything you need for an amazing vacation! We just renovated the entire house after Hurricane Ian so you'll get to enjoy a brand new kitchen (and huge island), new bathroom and new luxurious memory foam beds. Our pet fee is $75 per stay. 2 dogs max. NO cats please.

Top guest favourite

Home in Naples

5 out of 5 average rating, 6 reviews

Sunset Splash Luxe, Epic Pool, Hot Tub, Beaches

Sunset Splash is a luxury 3-bed, 2-bath (Sleeps 8) vacation rental in Naples, Florida. This gem offers quick access to the world's top beaches, fabulous restaurants, shopping (luxury shopping, too), and more. The property features a brand-new sizeable heated pool, hot tub, BBQ, outdoor shower, hammock, Wi-Fi, TVs in all rooms, dedicated work space, parking, and laundry room. Whether you're looking to relax by the pool or explore the nearby coastal gems, this home offers the best of both worlds

Superhost

Home in Fort Myers

4.77 out of 5 average rating, 30 reviews

*Cozy 2 BR * Waterfront Home With Heated Pool

Welcome to your home away from home. this 2-bedroom, 2-bath home with pool blends luxury & comfort, creating an unforgettable retreat for families, couples, or friends. Just a short drive from vibrant downtown Fort Myers, you’ll delight in exploring unique shops, delectable restaurants & exciting attractions. Enjoy quick access to stunning beaches, top-tier golf courses, & thrilling outdoor adventures. Feel free to fish in the backyard & enjoy your perfect getaway in this home upon the water!

Guest favourite

Home in Fort Myers

4.91 out of 5 average rating, 34 reviews

Why rent a hotel when you can have a pool home?

Relax with the whole family at this peaceful place to stay. Heated pool with propane BBQ in the pool area. Super spacious kitchen with inside dining for 6 and outside dining for 4 (total seating for 10 persons). No additional fee for pool heating or bbq. Fully fenced private back yard. Some pets allowed at additional cost with approval. Please text through app for animal approval prior to reservation. Please make sure the proper number of persons are on your initial reservation. Piano also.

Guest favourite

Home in Bonita Springs

4.83 out of 5 average rating, 18 reviews

Stunning Lakefront Heated Pool & Spa House!

Your perfect getaway awaits! Escape to tranquility in our beautifully updated 3/2 lakefront retreat with a heated (optional for a fee) pool and spa! This remodeled peaceful gem is nestled on a serene, private lot with breathtaking lake views. Just 7 miles to the pristine Bonita Beach and minutes from, shopping, and dining. Don’t miss out on this extraordinary retreat where comfort meets nature. Book your stay today and experience the ultimate in relaxation and luxury!

Superhost

Home in Cape Coral

4.86 out of 5 average rating, 43 reviews

Cape Oasis Pool Heater

.Enjoy a stylish experience at this centrally-located -5 minutes from Sunsplash water park -close to Sanibel beach -30 min from Fort Myers Beach -very closed to Sanibel Beach you can enjoy restaurant with amazing views and sunset . -minutes away from Matlacha seafood restaurants -4 bedroom -3 bathroom -2 car garage -new construction 2022 -Fantastic neighborhood - Plenty Backyard -Amazing modern pool -Barbecue Area -wine cooler

Guest favourite

Home in Cape Coral

4.96 out of 5 average rating, 166 reviews

Family Oasis: Waterfront Heated Pool & Game Room

This gorgeous vacation home boasts a luxury heated salt water pool and a relaxing jetted spa with views of a beautiful canal that provides direct access to three different lakes stocked with a great variety of freshwater fish. It's truly the ultimate dream getaway where guests come to comfortably unwind in a peaceful environment. Get away from it all and enjoy the gentle sound of the Florida breeze whispering through the palm trees!

Guest favourite

Home in Lehigh Acres

4.84 out of 5 average rating, 134 reviews

LIVING in PARADISE 🌴 ⛱️ 😎

Hotel accommodations with the comforts of home! Clean and beautiful house. Hot tub and pool, full grill Gazebo,patio for cookouts. Beautiful living room area, with a TV and family space. Dedicated dining room space, equipped with everything needed with a spectacular dinner. Kitchen is fully equipped. King , two queen beds. Beautiful full bathrooms. Close to Downtown Fort Myers, Bell Tower Shops, and Fort Myers Beach.

Top guest favourite

Home in Naples

4.96 out of 5 average rating, 24 reviews

South Exposure Heated Pool Home

Southern Exposure Heated Pool Home Look no further, this beach bungalow has the most amazing heated pool you will find, surrounded by tropical landscaping that is completely fenced in and private. Enjoy days grilling out by the pool and nights by the fire pit, this home has it all. This beach bungalow has been recently remodeled. The home features premium foam mattresses in every room and beautiful beachy chic decor.

Superhost

Home in Fort Myers Beach

4.95 out of 5 average rating, 126 reviews

Blue Lagoon w/ heated pool-2 min walk to beach

FMB Reg 19-1212 . Hurricane Ian caused damage to the island but the home is back fully operational as it was prior to the storm & beaches look great! Come be part of #FMBStrong! Check the Town of FMB or Chamber Websites for more info. No refunds outside our cancelation policy. TRAVEL INSURANCE IS HIGHLY RECOMMENDED FOR TRAVEL DISRUPTION.

Guest favourite

Home in Cape Coral

4.95 out of 5 average rating, 66 reviews

Casa Sevilla, heated pool, sleeps 9, 4/3, pets F

Relax with the whole family at this peaceful place. House equipped with everything you need to stay happy and relaxed in your vacation time, heated pool, game room to entertain the whole family, kitchen fully equipped to make those special dinners, 3 comfortable bathrooms,4 bedrooms, capacity for 9, pets friendly, safe for kids.

Guest favourite

Home in Cape Coral

4.9 out of 5 average rating, 48 reviews

Amazing Luxurious 3 bedroom Pool home! Three Palms

Your family will be close to everything when you stay at this centrally-located home. Restaurants, shopping, parks, waterpark, mini golf and of course many different and unique BEACHES! The home has been completely remodeled with high end finishes and has everything for your stay! Pool heat IS included in your stay.