Vacation rentals with a pool in Cypress Lake

Find and book unique homes with a pool on Airbnb

Top-rated rentals with a pool in Cypress Lake

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

0 of 0 items showing

1 of 3 pages

Superhost

Home in Fort Myers

4.83 out of 5 average rating, 167 reviews

Blue Beach Bungalow

3 large bedrooms (2 queens, one king) plus a full den, laundry room, HEATED pool and the house has its own beach with an in-ground fire pit that seats 12, lounge chairs, and sunset views! Walking distance to shopping centers, great restaurants, 20 minutes to RSW Airport and Fort Myers' white-sand beaches, perfect for a romantic get-away and 10 minutes from downtown Fort Myers Completely remodeled in July of 2021 with brand new appliances electronics, and all the creature comforts you can imagine

Top guest favorite

A serene pool area is showcased at dusk, featuring a screened lanai with a tranquil pool reflecting the colorful sunset sky. The surrounding patio is paved, with a tropical cabana visible in the background, creating a welcoming atmosphere for relaxation.

Home in Fort Myers

4.95 out of 5 average rating, 19 reviews

Private Poolside Oasis w/Pickleball &Game Room/Gym

Welcome to Aqua Blue, the perfect getaway in sunny Fort Myers, tucked away in a hidden neighborhood. This coastal-styled home was just completely remodeled, offering a stylish, updated, and serene environment with plenty of common space for gathering with friends & family. The backyard is a true oasis offering an expansive patio, pool with screened lanai, a tropical cabana, cozy white lights, a fire pit and outdoor patio, & seating for your entire group to spend time relaxing and dining outside.

Top guest favorite

The exterior of the home features a well-maintained façade with a combination of light brown stucco and stone accents. Lush greenery surrounds the entrance, including palm trees and flowering plants, complemented by a circular driveway and a clear blue sky overhead.

Home in Fort Myers

5 out of 5 average rating, 20 reviews

Casa Del Sol

Escape to paradise at Casa Del Sol. This updated home is located 14 miles from the airport in a quiet, upscale neighborhood, and is centrally located. Enjoy your days with a short drive to Sanibel, Fort Myers Beach or Lovers Key State Park. Shopping, restaurants, theaters, golf, and boating are all nearby and very abundant! Jet Blue Park and Hammond Stadium are under 10 miles. Enjoy your time relaxing at the house on the especially private lanai, with a heated plunge pool, BBQ and seating.

Guest favorite

A bright kitchen area is featured, showcasing a white table with a marble top and a bowl of oranges. Behind, large glass doors provide views of the outdoor screened pool area, which is furnished with a dining table and stylish seating.

Home in Fort Myers

4.97 out of 5 average rating, 179 reviews

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.

Top guest favorite

A private pool sits in a sunny backyard, surrounded by palm trees. Lounge chairs are positioned nearby, providing a space for relaxation. The clear water of the pool reflects the blue sky, while a dock is visible along the canal in the background.

Home in Cape Coral

4.99 out of 5 average rating, 151 reviews

Escape to the "Oasis"!

DISCOUNTS: Weeks...1=10%, 2=15%, 3=20%, 4=25%. Welcome to the "Oasis"! Escape to the water and stay on a canal in beautiful Cape Coral! Enjoy this 3 bedroom, 2 bath home. Swim in the pool, sit on the patio, fish from the dock, sit at the tiki bar for a drink, or take a nap on the lanai to get away from it all! There is a 50 foot long dock with 30 and 50 amps, so bring your boat! The Gulf is accessible by boat and Ft Myers Beach & Sanibel/Captive Island activities and beaches nearby!!

Top guest favorite

A serene outdoor space features a rectangular swimming pool surrounded by a spacious patio with patterned pavers. A red umbrella provides shade over one of the lounge chairs, while lush greenery borders the area, enhancing the inviting feel of the backyard.

Cottage in Fort Myers

4.98 out of 5 average rating, 121 reviews

20 min to the beach! Pool, fire pit, 3bd/2.5ba

*Zero damage in all of the hurricanes* Welcome to Double Palm Cottage located at 899 Dean Way, Fort Myers, FL. The 3-bedroom cottage with 2.5 baths and pool is situated in the Historial District directly off picturesque Royal Palm Tree lined McGregor Boulevard leading directly to the Edison and Ford Winter Estates. The cottage just 20 minutes to all the local beaches, shopping, and fine restaurants. Additional entertainment activities include Major League Baseball spring training games.

Top guest favorite

The living room features a spacious sectional sofa, providing ample seating. Large glass doors open to the outdoor area, enhancing natural light. A mounted TV displays beach scenery, while a modern fireplace adds a touch of warmth. The room's design promotes comfort and relaxation for guests.

Home in Cape Coral

4.97 out of 5 average rating, 110 reviews

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!

Top guest favorite

A screened-in patio area reveals a clean pool surrounded by lounging chairs. The pool features a gentle curve and easy access steps. Lush greenery and palm trees provide a serene backdrop, while the adjacent living space is faintly visible through large windows.

Home in Fort Myers

4.94 out of 5 average rating, 342 reviews

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.

Top guest favorite

A dining area is presented with a large wooden table surrounded by upholstered chairs. A centerpiece of greenery and fruit adorns the table. The walls are painted in a soft blue, complemented by decorative seahorse artwork and a stylish light fixture.

Home in Fort Myers

4.98 out of 5 average rating, 218 reviews

“Dream Vacation”Pool.Near airport&baseball

A few short miles from RSW International Airport, beaches, Twins/ Miracle's baseball, and downtown Ft. Meyers (McGregor). Walking distance to FSW Sunpark stadium. Safe and quiet neighborhood. Private pool *NOT HEATED*. Lanai TV has streaming service so you can log into your account. Click on our picture to view our five homes in Cape Coral/Ft. Myers/Delray Beach. All beautiful & with exceptional Super-host service and care.

Top guest favorite

A sparkling pool is nestled within a lush tropical landscape, surrounded by vibrant greenery and palm trees. Colorful floats rest on the water's surface, while a hammock invites relaxation nearby, creating a tranquil outdoor retreat.

Home in Fort Myers

4.9 out of 5 average rating, 145 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.

Superhost

An infinity pool is visible, offering views of calm waters and a clear blue sky. Sun chairs are positioned at the pool's edge, with the tranquil landscape creating a serene atmosphere. The surrounding area features stylish paved flooring and elegant architectural lines.

Home in Cape Coral

5 out of 5 average rating, 4 reviews

Intervillas Florida - Villa Xanadu

Introducing Villa Xanadu – Your Dream Vacation Awaits! Welcome to Villa Xanadu, a brand-new, luxurious retreat offering the perfect blend of comfort and sophistication. This exquisite 4-bedroom villa promises an unforgettable experience, whether you're seeking relaxation or adventure. Nestled in a prime boat-accessible location, Villa Xanadu boasts a massive infinity pool (33x15 ft) with an indulgent spa.

Top guest favorite

A comfortable living area is depicted, featuring a light gray sectional sofa and a stylish coffee table. A round mirror and decorative wall art enhance the space. The open kitchen and dining area are subtly visible in the background, creating a welcoming environment.

Townhouse in Fort Myers

5 out of 5 average rating, 10 reviews

Florida Vacation-Fort Myers-Pool-Gated Community

Private gated community at Sail Harbour 14 minutes from Fort Myers Beach. Large 3 bedroom on upper floor and convenient kitchen dining area with spacious TV area. 1 bathroom downstairs and 2 Full bathroom upstairs. Access to community pool. Quiet and friendly community. Lots of restaurants and amenities near by. Walking distance to Golisano Children’s Hospital of Southwest Florida.