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
A clear blue pool is surrounded by a spacious patio, featuring comfortable loungers partially immersed in the water. The inviting outdoor space overlooks the serene canal, while the covered lanai offers additional seating options. Lush palm trees sway gently in the background under a bright sky.
Home in Cape Coral
4.97 out of 5 average rating, 124 reviews

Boater’s Paradise-Stunning Sunsets! Games Room!

Renovated lanai! This 3 bed/4 bath home is on the nicest canal with 200+ ft of frontage & gorgeous views of the canal & sunset. The pool, tiki hut & docks have full sun all day. Each bedroom has a private bath & there's a 2 pc powder room off the laundry. The primary has a king bed & walkout to pool. The 2nd bedroom has a queen bed & pool access. Bedroom 3 has a queen & private bath. Fully equipped kitchen with everything you need. And a games room! Enjoy stunning sunsets under the tiki hut.

Top Guest favourite
The screened-in pool area features a serene swimming pool with shimmering water, two blue lounge chairs positioned nearby, and views of a wide canal. A thatched-roof Tiki hut can be seen across the water, surrounded by lush greenery.
Home in Cape Coral
4.99 out of 5 average rating, 231 reviews

LUX Villa w/ Private Salt Water Pool, Lanai, Canal

Are you looking to swim, relax outdoors, fish and take in beautiful sunsets on a wide gulf access canal? If so you will fall in love with this stunning newly constructed custom built home! The 2750 square foot home is bright & airy with two main bedroom on-suites & a separate family wing! The gourmet kitchen, dining room & great room open via large sliders to the lanai & pool w/ views of the canal in much desired SW Cape! Beach inspired villa! Large captains walk & Tiki! Check out our reviews!

Top Guest favourite
A spacious living area features a leather sofa with a wooden coffee table at its center. Large windows invite natural light, complemented by a ceiling fan above. To the rear, the open layout leads to a dining area and kitchen, enhancing the bright and airy atmosphere.
Home in Cape Coral
4.98 out of 5 average rating, 109 reviews

Turkey Day Sale! Hot Tub/Games/Pets+5 min to Town

-5 min to Downtown Cape/10 min to Yacht Club Beach, 20 min to Causeway Beach, 25 min to Ft Myers & Sanibel Beach -Tropical fenced backyard w/ pool, hot tub, gas firepit, swing chair, hammock & Blackstone grill -Beach essentials, boogie boards, umbrellas, beach wagon, cooler & chairs -Board games, ping-pong, corn-hole, darts, 2 kayaks+life jackets -2 Beach Cruiser bikes + helmets -Relaxing enclosed covered patio + string lights, neon sign & grass wall -Canal access for kayak launch 5 min away

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, 167 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 favourite
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
4.97 out of 5 average rating, 133 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.

Guest favourite
Home in Fort Myers
4.83 out of 5 average rating, 185 reviews

Blue Beach Bungalow

3 large bedrooms (3 king sized beds) with TV in everyroom, 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,

Top Guest favourite
Home in Fort Myers
4.94 out of 5 average rating, 356 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 serene backyard showcases a sparkling pool surrounded by light-colored pavers. Five lounge chairs with colorful striped towels are positioned poolside, inviting relaxation. Lush greenery and a wooden fence frame the area, creating a private and tranquil outdoor space.
Home in Fort Myers
5 out of 5 average rating, 10 reviews

NEW Coastal, Eclectic, Pool & Bikes, Sleeps 9

Welcome to your coastal haven! This home effortlessly blends the soothing allure of coastal living with the vibrant energy of eclectic design. This 4 Bed 2 Bath home is just minutes away from highly desirable shopping plazas, restaurants and two well known beaches - Fort Myers and Sanibel. Spend your days lounging by the pool, playing bocce ball in the backyard, or going for a bike ride. Grill out under the cabana and enjoy dinner on the screened in lanai.

Top Guest favourite
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, 224 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.

Guest favourite
Home in Fort Myers
4.9 out of 5 average rating, 158 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.

Top Guest favourite
A spacious outdoor area features a heated pool surrounded by a paved deck. Comfortable lounge chairs and an umbrella are positioned nearby, offering a relaxing space. The backyard is framed by greenery and a fenced perimeter, ensuring privacy and a serene ambiance.
Villa in Cape Coral
5 out of 5 average rating, 132 reviews

Casa Capri | Heated Pool | No Service Fee

Escape to Luxury! We've got you covered - no service fees! Discover our 5-star Cape Coral retreat: high-speed WiFi, smart TVs, premium bedding, and more. Unwind in style and serenity. Your peaceful haven awaits! Nestled in the heart of Cape Coral, our meticulously designed space promises an unforgettable stay for the discerning traveler. Relax with the whole family at this peaceful place to stay.

Top Guest favourite
A serene pool area is highlighted by a spacious lounge chair positioned beside a sparkling pool. The water is illuminated in soft turquoise tones, with decorative lighting enhancing the atmosphere as a vibrant sunset sky is visible through the screen enclosure.
Home in Fort Myers
4.97 out of 5 average rating, 36 reviews

Sunny Coastal Getaway w/ Heated Pool Near Beaches

Welcome to The Mermaid Lounge! Your sunny coastal getaway with a private heated pool, minutes from beautiful beaches and family-friendly dining. We’ve thought of everything — 3 coolers, 6 beach chairs, wagons, pool floats, toys, games, and baby gear so you can pack light. Enjoy mornings with coffee by the pool and evenings with bubbly while the kids play. Relax, connect, and make lasting memories!

Popular amenities for Cypress Lake rentals with a pool

When is the best time to visit Cypress Lake?

MonthJanFebMarAprMayJunJulAugSepOctNovDec
Avg. price$297 NZD$274 NZD$297 NZD$279 NZD$244 NZD$210 NZD$230 NZD$228 NZD$228 NZD$242 NZD$230 NZD$311 NZD
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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 $35 NZD per night before taxes and fees

  • Verified guest reviews

    Over 1,280 verified reviews to help you choose

  • Family-friendly holiday rentals

    70 properties offer extra space and kid-friendly amenities

  • Pet-friendly accommodation

    Find 20 rentals that welcome pets

  • Rentals with dedicated workspaces

    40 properties have a dedicated workspace

  • Wi-Fi availability

    80 of Cypress Lake holiday rentals include Wi-Fi access

  • Popular amenities for guests

    Guests love Kitchen, Wi-Fi and Pool across Cypress Lake rentals

  • 4.9 Average rating

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

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