
Vacation rentals with a pool in Cypress Lake
Find and book unique homes with a pool on Airbnb
Quick stats about vacation rentals with a pool in Cypress Lake

Total vacation rentals
Explore 80 vacation rentals in Cypress Lake

Nightly prices starting at
Cypress Lake vacation rentals start at ﺩ.ﺇ 73 per night before taxes and fees

Verified guest reviews
Over 1,390 verified reviews to help you choose

Family-friendly vacation rentals
70 properties offer extra space & kid-friendly amenities

Pet-friendly vacation rentals
Find 20 rentals that welcome pets

Rentals with dedicated workspaces
40 properties have a dedicated workspace

Wi-Fi availability
80 of Cypress Lake vacation rentals include wi-fi 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!
Top-rated rentals with a pool in Cypress Lake
Guests agree: these homes with a pool are highly rated for location, cleanliness, and more.

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

Lakeview Oasis- Condo Near Sanibel/Ft Myers Beach
Welcome to your Florida escape! This cozy 2nd floor condo / townhouse is the perfect retreat off McGregor Blvd & only 10 minutes from Sanibel & Ft Myers Beach. Savor morning coffee on the screened porch overlooking a tranquil lake, swaying palms, & local wildlife. Unwind at the resort style pool, enjoy pickleball, tennis & the putting green. Or, stay fit in the clubhouse gym. Close to golf, a marina, fine dining, boutiques, and coastal adventures- perfect for seasonal snowbirds or weekly stays.

Palm Palace - Two House Compound Sleeps up to 22!
This property listing includes full access to two separate on-property houses, both with full access to the pool and giant screened lanai! The main house has 3 bedrooms, 2.5 bathrooms and 8 total beds (1 king, 1 queen, 2 double bunk beds & 2 sofa beds). The smaller "pool house" has an additional full kitchen, living room, 2 additional bathrooms & 3 more beds (2 queen & a sofa bed)! This property frequently is booked by multi-generational families, large groups and even entire sports teams!

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!

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

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.

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,

Serene Pool & Spa Home near Beaches & Downtown
Where prime location meets tropical paradise. Welcome to your very own private poolside and spa oasis, minutes from the beach! Close to Sanibel Island, Fort Myers Beach & Bunche Beach, as well as local shopping, amazing restaurants, fun nightlife in Downtown Fort Myers and the winter homes of Thomas Edison & Henry Ford. Fully renovated throughout. This remarkable space can accommodate up to 10 guests, making it the perfect destination for a family or friends vacation!

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.

Townhouse in Fort Myers
Enjoy Fort Myers at its finest while staying in this newly renovated 2 bedroom, 2 bathroom townhome. This quiet gated community offers a pool and spa directly across the parking lot from this unit. LOCATION! LOCATION! LOCATION! Sanibel Island, Fort Myers International airport and downtown Fort Myers all within a 20 minute drive. A variety of activities like putt putt golf, trampoline park, family fun center and lots of shopping only a few minutes away.

Dolphin beach house 2
ONE OF THE BEST WATERFRONTS IN CAPE CORAL! A short walk to the beach . This 2,500+sq ft home has stunning sunsets and South Western water views from all main living areas,as well as the Master Suite. Heated pool w/ LED colored lighting, built in Spa,Pool bath, full laundry facility, Lanai,Fireplace ,Wi-fi and TVs in every bedroom, private dock . Boat on lift for rent w/RPM rentals . Large 2-car garage w/5 bicycles,beach wagon & cooler on site.

“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.
Popular amenities for Cypress Lake rentals with a pool
House rentals with a pool

Luxury Waterfront Escape - Private Pool & Jacuzzi

Skyline Tides- Gulf Access- Wide Views- Heat Pool

Cape Serenity- Luxury Waterfront Residence

Gather By The Sea! Close to the beach! Heated Pool

Sunny Fort Myers Home with Convenient Location

Intervillas Florida - Villa Dolphin Drive

Lovely home nestled near Sanibel & Ft. Myers Beach

Casa Del Sol
Condo rentals with a pool

Sunny Florida condo!

Rare walkout condo on Sanibel beach

2 Bed 2 Bath Townhouse with Loft - 6B

Beachfront fully equipped apartment

Ft Myers Beach & Lovers Key State Park- FANTASTIC!

Spacious clean condo

Beachfront Escape w/ Sunset Views, Pool & Hot Tub

2nd Floor Beachfront Condo Sanibel Harbour
Other vacation rentals with a pool

Palm Breeze | 10 PPL | Pool | Games|BBQ & Fire Pit

Florida Vacation-Fort Myers-Pool-Gated Community

Robin's Nest on a Canal with River and Gulf access

Sleep over the water- Boathouse with Private Dock

NEW Coastal, Eclectic, Pool & Bikes, Sleeps 9

Waterfront 2BR 2BA SE Cape Coral Condo!

Cheers to Paradise: Pool, Tiki Bar, & Endless Fun!

3/2 Luxury Sailboat Access Pool & Spa Cape Harbour
When is the best time to visit Cypress Lake?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | ﺩ.ﺇ 679 | ﺩ.ﺇ 698 | ﺩ.ﺇ 716 | ﺩ.ﺇ 580 | ﺩ.ﺇ 507 | ﺩ.ﺇ 437 | ﺩ.ﺇ 477 | ﺩ.ﺇ 474 | ﺩ.ﺇ 474 | ﺩ.ﺇ 496 | ﺩ.ﺇ 558 | ﺩ.ﺇ 602 |
| Avg. temp | 16°C | 18°C | 19°C | 22°C | 25°C | 27°C | 27°C | 28°C | 27°C | 24°C | 21°C | 18°C |
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