Holiday rentals with a pool in Cypress Lake

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Top-rated rentals with a pool in Cypress Lake

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

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Top guest favourite
An outdoor heated pool is enclosed within a screened patio, featuring a spacious deck with lounge chairs. Lush greenery surrounds the area, and sunlight fills the space, creating an inviting atmosphere for relaxation. The pool's clear water reflects the bright blue sky above.
Home in Fort Myers
4.95 out of 5 average rating, 124 reviews

McGregor’s Gem• Heated Pool 3BR/2BA River District

🌴 Welcome to McGregor’s Gem—your ideal Southwest Florida retreat! Dive into relaxation in your private heated pool, spread out across three bedrooms and two baths, and enjoy the perfect blend of peaceful tree-lined neighborhood living just minutes from the charming Downtown Fort Myers River District, world-class beaches, and top local attractions.☀️ Whether you’re traveling with family, friends, or on business, this home offers all the modern comforts you need for a relaxing, stress-free stay

Superhost
Home in Fort Myers
5 out of 5 average rating, 3 reviews

Golf>Heated Pool • Sleeps 10 • Near Beach

Welcome to SELBY GOLF HOME – Your Luxury Getaway in Fort Myers .12 mins to Downtown Fort Myers .18 mins to Fort Myers Beach .30 mins to Sanibel & Captiva Islands .Less than 5 mins to nearby golf courses .Sleeps up to 10 guests .3 King beds + 2 Full beds .Private pool .Fast Wi-Fi .Washer & dryer .Safe & quiet neighborhood .Free parking .Self check-in for easy access .Pool table .Ping pong table .Mini golf area .Poker table .Kids play area .Outdoor grill .Fire pit lounge Private patio & terrace

Top guest favourite
The outdoor area showcases a large pool surrounded by stone patio flooring. Comfortable lounge chairs are positioned beside the pool. Lush greenery and palm trees frame the space, contributing to a private and tranquil setting.
Home in Fort Myers
4.94 out of 5 average rating, 156 reviews

Paradise on Estero Bay

Welcome to Mullock Creek a Boater's dream! Southwest views boasting breathtaking sunsets overlooking gulf access canal from your spacious backyard, just minutes away from shopping and dining at Coconut Point, and Gulf Coast Town Center. This stunning Key West Style home has been beautifully maintained and updated offering a lovely front entrance, fully equipped kitchen, spacious Living Room, dining room, Wi-Fi, private driveway with access to the open garage, fully furnished and private pool.

Top guest favourite
A living area is featured, displaying a neutral-colored sofa complemented by colorful cushions. A wooden coffee table holds a decorative plant and coastal-themed items. Two patterned chairs provide additional seating, while warm light filters in, adding a welcoming ambiance to the space.
Home in Fort Myers
4.96 out of 5 average rating, 48 reviews

Mermaids Cove, don't miss this listing!

Mermaid's Cove is a private tropical retreat ready for guests to relax and refresh! It is a beautifully decorated home with a private pool & bedroom /bathroom on opposite ends of the home. The kitchen is fully equipped open concept. It is located in a friendly, family neighborhood near everything Ft. Myers has to offer. If you enjoy palm trees swaying as you float in the pool or sitting under a patio umbrella while grilling dinner, then this home is for you. Come and renew at Mermaid's Cove!

Top guest favourite
A well-maintained canal property is highlighted by palm trees and a spacious lanai. A 50-foot dock is visible, accommodating watercraft with a boat lift. Colorful Adirondack chairs are placed along the dock, enhancing the outdoor experience beside the tranquil water.
Home in Cape Coral
4.99 out of 5 average rating, 179 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!!

Guest favourite
Home in Fort Myers
5 out of 5 average rating, 7 reviews

4BR Waterfront Home w/ Heated Pool & Private Dock

Waterfront Coastal Retreat | Heated Private Pool + Dock | Dining + Beaches Unplug, unwind, and settle into effortless coastal living at this beautifully renovated 4-BR waterfront home in Fort Myers’ quiet, upscale Town & River neighborhood. You’ll enjoy a peaceful setting while staying close to everything—so many local restaurants are just minutes away, and the area’s best beaches are an easy drive: Sanibel Island beaches are about 15 minutes (9.6 mi) & Fort Myers Beach is about 18 mins

Top guest favourite
A spacious heated pool invites relaxation, bordered by lounge chairs and a vibrant red umbrella offering shade. The clear water reflects the surrounding greenery, while expansive water views showcase the peaceful canal, enhancing the tranquil outdoor setting.
Home in Cape Coral
4.99 out of 5 average rating, 149 reviews

Waterfront Villa•Heated Pool•Dock•Fishing•Kayaks•

Welcome to Sprocket Boathouse, a dream waterfront escape. Beautiful views, a sparkling heated pool overlooking one of the widest canals in Cape Coral, and with western sun exposure, the house gets ☀️ all day. Don’t miss the incredible sunsets and sunrises! You won’t be disappointed. Spend hours swimming, kayaking or fish off your own private dock (kayaks & rods included.) Make sure to keep a look out for all the wildlife! You can spot iguanas, turtles & herons on the waterfront.

Top guest favourite
A resort-style pool area is showcased with a stone patio, featuring several lounge chairs and two shaded umbrellas. Palm trees stand nearby, and a rock formation is visible within the pool's edge, complementing the serene outdoor setting.
Home in Fort Myers
4.92 out of 5 average rating, 121 reviews

Experience of a lifetime

Get ready for the experience of a lifetime at this hidden gem! As you walk through the front door you will begin your journey into the best vacation of a lifetime. Keep on going through the sliders & that will lead you to the incredible resort style pool that will leave you in awe!!! Here you are in the heart of it all. Shopping-dining-entertainment is all within a 5 minute drive. The beautiful beaches just 7 miles away. If you enjoy boating & relaxing this is the place for you.

Guest favourite
Home in Fort Myers
4.95 out of 5 average rating, 19 reviews

Swimsational Golf views

Recently updated heated pool home backing to a golf course with private back yard. It has a covered patio area with new furniture and outdoor grill. Both bedrooms have televisions and super comfy pillows / linens. The main area has a coffee/tea bar and island in the kitchen. The garage has a brand new washer/dryer with the latest technology. Located in a great residential neighborhood surrounded by shopping and restaurants. 20 minutes to the beaches or downtown Ft. Myers.

Guest favourite
Home in Cape Coral
4.89 out of 5 average rating, 122 reviews

Cape Serenity- Luxury Waterfront Residence

This beautiful, fully equipped home is located in the lovely Orchid neighborhood. As the name suggests, serenity will wash over you as you relax and unwind in this gorgeous 3 bed, 3 bath home. Located off of the Caloosahatchee River, this is one of the select few homes in the Cape Coral/Fort Myers area that affords both privacy/luxury and direct accessibility to the gulf. Recent upgrades include a newly refinished pool deck and EV charger to enhance your experience!

Guest favourite
Home in Fort Myers
4.94 out of 5 average rating, 381 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.

Guest favourite
A screened lanai features a rectangular pool surrounded by tropical greenery. Outdoor dining furniture is visible near a glass table, offering a place to enjoy meals. Colorful pool floats and lounge chairs add to the inviting space, with the waterfront just beyond the pool area.
Home in Cape Coral
4.84 out of 5 average rating, 112 reviews

Peaceful Oasis

Enjoy the best of the Cape Coral Yacht Club neighborhood. We offer beautifully restored Terrazzo floors along with all new cabinetry, appliances and furniture. The interior of the house has been greatly improved since Hurricane Ian. The lanai, pool and waterfront offer you serene splendor and beauty that you will not want to leave. We provide the most convenient location in Cape Coral, just one mile from the downtown restaurant district.

Popular amenities for Cypress Lake rentals with a pool

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Quick stats about holiday rentals with a pool in Cypress Lake

  • Total holiday rentals

    Explore 80 holiday rentals in Cypress Lake

  • Nightly prices starting at

    Cypress Lake holiday rentals start at € 17 per night before taxes and fees

  • Verified guest reviews

    Over 1,390 verified reviews to help you choose

  • Family-friendly holiday rentals

    70 properties offer extra space & child-friendly amenities

  • Pet-friendly holiday rentals

    Find 20 rentals that welcome pets

  • Rentals with dedicated workspaces

    40 properties have a dedicated workspace

  • Wifi availability

    80 of Cypress Lake holiday rentals include wifi access

  • Popular amenities for guests

    Guests love Kitchen, Wifi and Pool across Cypress Lake rentals

  • 4.9 Average rating

    Cypress Lake stays are highly rated by guests – averaging 4.9 out of 5!

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