
Holiday 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.

Beautifully Remodeled 2 Bedroom With Water View 1G
Welcome to Coral Waters 1G! Close to Hammond Stadium & beaches! This beautifully remodeled 2 bed 2 bath apartment is situated perfectly for you to relax & enjoy the water view in your back yard. Take a dip in the heated pool or play a game of shuffleboard. You will love this fresh, clean, recently remodeled home w/ everything you need for a relaxing time in sunny SW Florida! Golf courses, restaurants, grocery stores, shopping & MN Twins spring training close by! (Unit is on 2nd level w/ stairs).

Ft. Myers Quaint Getaway! Minutes from Beach!
My condo is close to the beach, NOT on the beach, nightlife, public transport, and family-friendly activities. It is good for couples, solo adventurers, business travelers, and families (with kids). It's minutes from Ft. Myers and Sanibel Beach. It has a King size bed in the master bedroom and two twin murphy beds in the guest room. Walking distance from a Super Target. Several outlet malls, closest is 2 miles. FYI, not handicap accessible (second floor unit). A few steps to the pool and grill.

Gather By The Sea! Close to the beach! Heated Pool
Large Heated Pool! Catch your favorite sports game or movie from the outdoor tv while floating in the pool! Large outdoor dining area and outdoor grill to cook for large families! Very close to the worlds most beautiful beaches! Close to amazing restaurants! This home is completely remodeled on the inside! Everything is brand new! The home includes tons of supplies for all your pool and beach trips! The kitchen is fully stocked to handle cooking for larger families! Pet & family friendly!

Resort Life in Heritage Palms
Paradise awaits! This newly renovated, bright unit has a spectacular golf and water view from your double-sided lanai overlooking the 38-acre lake. Walking distance to club house, golf, tennis, fitness and pools make this one of the best units in Heritage Palms. Something for everyone! 36 holes of golf, 8 tennis courts, 9 pools, 3 restaurants, pickleball, state of the art fitness center, poolside tiki-bar, bocci ball and walking trails galore! Close to airport, restaurants and beaches!

Seabreeze Hideaway
Located in Sun Retreats Fort Myers Beach (formerly Indian Creek), just 3 miles from Fort Myers Beach, Bunche, and Sanibel Island, and Margaritaville. The property offers amenities, including pools, pickleball, tennis, and numerous activities. It’s a great location, away from the main beach traffic but still close to shopping. The trolley also stops right at the entrance. The bungalow features a fully equipped kitchen and allows one pet up to 20 pounds. An occupant must be 35 or older.

Stylish 2 Bedroom 2 Bath Townhome with Pool!
Kick your shoes off and relax with your friends and family in this stylish townhome steps from a refreshing dip in the pool. Enjoy the beach only 20 minutes south down Summerlin Dr or head 15 minutes north down 41 to trendy down town Fort Myers. Being in the heart of the city means you’re close to everything that makes you feel at home. With a desk in each room JetSetStā Parkwoods is a perfect spot to catch up on business while taking advantage of the beautiful Florida sun.

Luxury II
Because one wasn’t enough… we’re opening Luxury 2 🥂 Experience even more elegance and the same breathtaking river views you loved. This brand-new unit blends modern luxury, romantic vibes, and unforgettable sunsets. 📍 In the heart of Downtown Fort Myers, steps from top restaurants, bars, and art. 🛏️ Stylish interiors | 🌅 Floor-to-ceiling views | 🏊 Resort amenities | 🍷 Romantic & vibrant Luxury 2—your escape to unforgettable memories. #Luxury2 #LuxuryInTheSky

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.

“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.

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!

Modern Oasis pool paradise
Location! Location! The entire place. This is a brand new Condo with gorgeous pool located next to supermarkets, restaurants including famous seafood restaurant, very close to Captiva, Fort Myers and Sanibel beaches Beautiful modern decor quiet secluded amazing!!! Great pool. No pets no service dogs no comfort pets allowed owner is allergic.

Cathy Condo
Perfect second floor condo that makes you feel right at home but you are now just minutes awayfrom Fort Myers Beach and Sanibel Island! There is tons of shopping and restaurants close by and a marina right across the street! Come stay at my place for a month or more and enjoy Southwest Florida’s great beaches and weather!
Popular amenities for Cypress Lake rentals with a pool
House rentals with a pool

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

***Relaxation Awaits*** Heated Saltwater Pool Home

Yacht Club Beauty....walking distance to the beach

Serene Modern Oasis | Private Pool in Fort Myers

Peaceful Oasis

Waterfront Home w/ Pool. Minutes to Sanibel

Heated Pool & Game Room Waterfront Family Retreat

Modern New-Build Luxury Villa!
Apartment rentals with a pool

Beachfront @ Elevate in the Sun!

Cozy Coastal Escape. Close to FMB and Sanibel

Bonita Beach and Tennis 1903

Gulf Water Views + 2 bikes, beach gear weekly stay

Ft Myers Beach & Lovers Key State Park- FANTASTIC!

2nd Floor Beachfront Condo Sanibel Harbour

Luxury Condo by Cape Harbor and Excellent Dining!

Bonita Beach and Tennis 3907 - Ocean Views
Other holiday rentals with a pool

Adorable Cottage with Heated Pool -Jaccuzi - Sauna

Amazing View of Sanibel Harbour

Heated Pool, GameRoom, EV Charger, Family Friendly

VRCC Villa The Beach

Waterfront Condo with Pool & Boat Slip

Villa Royal on XXL-Canal with Sailboat Access

Cape Coral Home with Huge Heated Pool & Lanai

Renovated modern home with Big pool & Ocean access
When is the best time to visit Cypress Lake?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | £123 | £113 | £123 | £116 | £101 | £87 | £95 | £94 | £94 | £100 | £95 | £129 |
| 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 |
Quick stats about holiday rentals with a pool in Cypress Lake

Total holiday rentals
Explore 90 holiday rentals in Cypress Lake

Nightly prices starting at
Cypress Lake holiday rentals start at £15 per night before taxes and fees

Verified guest reviews
Over 1,300 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!
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- Naples Beach
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