Vacation rentals with a pool in Cypress Lake

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Popular amenities for Cypress Lake rentals with a pool

House rentals with a pool

Guest favorite
A heated pool sits within a screened patio, surrounded by brick pavers. The pool area features a seating arrangement covered by an awning, inviting relaxation. Lush greenery and well-maintained landscaping are visible beyond the enclosure, providing a peaceful outdoor setting.
Home in Fort Myers
4.91 out of 5 average rating, 66 reviews

Paradise Central - Cozy 3 BR home w/ pool & lanai

MichaelRating, 5 stars6 months ago
What a great place. My family and I were told about Fort Myers, FL for years now so, I'm excited to have seen it for ourselves. The house was amazing. Set up for family fun. Thank you so much.
Top guest favorite
A tranquil heated saltwater pool is surrounded by lush tropical plants and palm trees, providing a serene atmosphere. The pool features smooth, curved edges and reflects the clear blue sky above, enhancing the scenic freshwater canal views.
Home in Pelican
4.96 out of 5 average rating, 50 reviews

New Gorgeous Smart Home with Heated Pool on the Ca

DavidRating, 5 stars1 month ago
Beautiful property! Lots of space and plenty to do. Dev is a great host! We will be sending guests his way in the future!
Top guest favorite
A private heated pool features a tanning shelf and is surrounded by a spacious patio. Lush greenery along the perimeter enhances the waterfront view. The clear blue water invites relaxation and leisure, while the tranquil setting provides a serene atmosphere.
Home in Pelican
5 out of 5 average rating, 28 reviews

Heater Pool -Stunning views 4Brm-3BA W/fishing

LaurenRating, 5 stars3 days ago
The house was very spacious and clean. The beds were comfortable and pool was fantastic. Really enjoyed our brief stay.
Guest favorite
An in-ground pool is situated within a screened enclosure, showcasing clear blue water and a lounge float. Comfortable seating arrangements are positioned beside the pool, surrounded by greenery. Ceiling fans are visible overhead, contributing to a relaxed atmosphere.
Home in Fort Myers
5 out of 5 average rating, 33 reviews

Private Heated Pool, 7 minutes to the beach

MinelixRating, 5 stars1 week ago
Thank you so much Tetyana, staying in your home was just what the doctor ordered. Everything was perfectly clean and comfortable and the beaches were close by.
Top guest favorite
A spacious swimming pool is enclosed within a fully screened area, featuring clear blue water that reflects the sky above. Lush greenery and water views are visible beyond the pool, enhancing the serene outdoor environment.
Home in Caloosahatchee
5 out of 5 average rating, 23 reviews

Luxury Private Pool Home with Water View

AmyRating, 5 stars1 week ago
Our stay here was perfection! From the immaculate home & beautiful furnishings, it had absolutely everything we needed. It was spotless & it was evident the owners didn’t spare a dime with the decor. Amy was quick to respond any time we reached out. It was so peaceful & just what we were looking forward to. We plan to return again & won’t hesitate to recommend this home to friends & family. 5 star stay, for sure! Thank you, Amy
Top guest favorite
An aerial view captures the serene waterfront home surrounded by lush landscaping. A private pool is set within a spacious backyard, bordered by palm trees. The boat slip is visible along the canal, providing easy access for water activities.
Home in Caloosahatchee
5 out of 5 average rating, 16 reviews

Waterfront Retreat with Private Pool & Boat Slip

GerdaRating, 5 stars4 days ago
Very beautiful home. Great location. Host is very responsive and provided some great recommendations for my family to visit in the area.
Superhost
Home in Pelican
4.97 out of 5 average rating, 33 reviews

NEW Luxury Pool Home, Jacuzzi, largeTropical Oasis

LarryRating, 5 stars4 months ago
We had a great time at Suzy’s listing. This is a beautiful, modern, oasis. It out did our expectations and even after nearly 3 weeks there we were sad to leave. The professionalism and thoughtful touches set a high bar for our future travels. I would highly recommend this house and would certainly stay there again.
Top guest favorite
A spacious bedroom is highlighted by a large bed dressed in crisp linens and layered with a green throw blanket. Two chairs are positioned near large windows, allowing natural light to fill the room. Art featuring botanical designs adorns the wall, complementing the soft color palette.
Home in Fort Myers
5 out of 5 average rating, 12 reviews

Tropical Haven in Ft. Myers w/ heated pool.

MikeRating, 5 stars2 months ago
The house was aesthetically pleasing. I had good communication with Joanna. This is a small thing but I really appreciated that she had coffee and filters on hand. Nice pool and the property is well kept. I would stay here again.

Condo rentals with a pool

Guest favorite
A modern kitchen features light grey cabinetry and stainless steel appliances, including a coffee maker and microwave. Natural light illuminates the space through a window above the sink, which is complemented by a sleek blue faucet. The countertop provides ample workspace.
Condo in Fort Myers
4.83 out of 5 average rating, 112 reviews

Cute Coastal Escape. Close to FMB and Sanibel

YolandaRating, 5 stars2 weeks ago
Lisa's place was exactly as described—clean and convenient. It was 5 minutes to Ft. Myers and 15 minutes to Sanibel. Unfortunately, I didn't have time to enjoy the pool, but it couldn't have been in a better spot (directly in front of the condo), and Lisa had plenty of pool and beach toys available. Great stay! If I make it down there again, I would definitely stay at Lisa's place.
Guest favorite
A serene view of the Gulf of Mexico features soft waves lapping against a sandy shore, with clear turquoise water meeting an expansive blue sky. The adjacent image shows the condo's exterior with lush green landscaping, highlighting multiple units in a welcoming and well-maintained setting.
Condo in Sanibel
4.89 out of 5 average rating, 244 reviews

Rare walkout condo on Sanibel beach-Fully Restored

AnnastaciaRating, 5 stars1 week ago
absolutely gorgeous condo with walkout to the beach. it was spacious and clean and he was accommodating in allowing us to get in a little earlier than normal check in. high recommend this place I will defiantly be booking here again!
Guest favorite
Condo in Fort Myers
4.95 out of 5 average rating, 20 reviews

Glamorous Fort Myers Getaway! Condo Resort Style!

JodyRating, 5 stars11 months ago
Perfect location. Close to restaurants and shopping. Fabien was extremely responsive. Place was spotless and pool is close by. Definitely would stay here again!
Guest favorite
A inviting living area features sliding glass doors that open to a private balcony. The tray table holds books showcasing local attractions. Bright natural light fills the space, illuminating the coastal decor, while expansive ocean views can be seen beyond the balcony railing.
Condo in Fort Myers Beach
4.81 out of 5 average rating, 108 reviews

EBT 206C Exceptional Panoramic Gulf Views +2 Bikes

EricRating, 5 stars3 days ago
We had an incredible week at this beautiful Ft. Myers Beach condo! From the moment we booked, Caihlin was warm, responsive, and extremely thoughtful—providing clear check-in instructions, local tips, and even a care package that made us feel right at home. The location was unbeatable. Mornings spent sipping coffee on the deck while watching dolphins glide by felt like a dream. The beach, just steps away, was private and peaceful—a perfect escape from the crowds. We tried several of the recommended restaurants and weren’t disappointed once. It’s clear Caihlin truly knows and loves this area. We left feeling refreshed, grateful, and already plotting our return. Highly recommend this stay to anyone looking for a little slice of paradise!
Superhost
A sparkling pool features a waterfall and is surrounded by palm trees. Lounge chairs are positioned around the pool area. In the background, views of the bay are visible under a clear blue sky, creating a serene vacation atmosphere.
Condo in Fort Myers Beach
4.92 out of 5 average rating, 198 reviews

Ft Myers Beach & Lovers Key State Park- FANTASTIC!

RobinRating, 5 stars1 month ago
Lover’s Key is a lovely low key and private place to stay! This is our 4th anniversary here in Ft Meyers. Our time here never disappoints. John’s place has what you need but we always bring extra TP, dishwasher cubes and laundry cubes. Just makes it easier… Flipper’s restaurant is right outside the door. Good food and good drinks! Key Lime Colada was delish! Lastly, please remember that Ft Meyers is still in a rebuilding phase, it’s taken a couple of years to get the bridge re built. There are plenty of things to do downtown and surrounding areas. We look forward to next year!
Superhost
Condo in Pelican
4.91 out of 5 average rating, 23 reviews

Grand Outdoor Patio-Luxury Master, Water Views

BrendaRating, 5 stars3 weeks ago
We enjoyed our stay. The only thing that we didn’t enjoy is the pool that was next to our place was very small and no umbrella for sun protection. The 2nd pool was located in the club house that was about a mile away and that pool wasn’t very big either. Other than that the place was great. Quiet and very spacious
Guest favorite
A living area features a black leather sofa, accent chairs, and a flat-screen TV on a light-colored media console. Two framed botanical prints are displayed on a yellow wall, while large sliding glass doors provide sweeping views of the bay and natural light.
Condo in Fort Myers
4.97 out of 5 average rating, 121 reviews

2nd Floor Beachfront Condo Sanibel Harbour

TroyRating, 5 stars3 days ago
We had a fantastic stay at this condo! The place was clean, comfortable, and exactly as described. The location was perfect—close to everything but still quiet and relaxing. Check-in was super easy, and the host was friendly and responsive. We loved having coffee on the lanai each morning and looking for dolphins and manatees. We would definitely stay here again! Taylor family
Top guest favorite
A spacious pool area is surrounded by palm trees, offering a serene environment. The clear water reflects the sky, with lounge chairs placed nearby on a tiled surface. A fence provides privacy, and a shaded area can be seen in the background.
Condo in Bonita Springs
4.98 out of 5 average rating, 130 reviews

Casa Bonita - Relax @ The Beach (Newly Remodeled)

MiriamRating, 5 stars1 week ago
My husband and myself really enjoy our time there please with spotless easy to get to across the street from the beach restaurants close by people were friendly and I really enjoyed my time. Thank you, Rose.

Quick stats about vacation rentals with a pool in Cypress Lake

  • Total rentals

    80 properties

  • Total number of reviews

    1.1K reviews

  • Family-friendly rentals

    60 properties are a good fit for families

  • Pet-friendly rentals

    20 properties allow pets

  • Rentals with dedicated workspaces

    40 properties have a dedicated workspace

  • Wifi availability

    80 properties include access to wifi

Destinations to explore

  1. Airbnb
  2. United States
  3. Florida
  4. Lee County
  5. Cypress Lake
  6. Rentals with pools