
Family-friendly vacation rentals in Cypress Lake
Find and book unique family-friendly homes on Airbnb
Quick stats about vacation rentals that are family-friendly in Cypress Lake

Total vacation rentals
Explore 80 vacation rentals in Cypress Lake

Nightly prices starting at
Cypress Lake vacation rentals start at G$4,185 GYD per night before taxes and fees

Verified guest reviews
Over 1,970 verified reviews to help you choose

Pet-friendly vacation rentals
Find 20 rentals that welcome pets

Vacation rentals with a pool
70 properties feature pools

Rentals with dedicated workspaces
40 properties have a dedicated workspace

Wi-Fi availability
70 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 family-friendly rentals in Cypress Lake
Guests agree: these family-friendly homes 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
Indoor spacesFamilyPool

“Ft. Myers Getaway” BBQ+Close to Everything
The best location, period. This very quiet and private one bedroom apartment has paved & shaded parking . Black out rolls on windows. Private courtyard with Gas grill, side burner sink and counter. Kitchenette with Microwave and supplies. 1 block from Publix, 3 from Costco. Walk to FSW College, Barbara B Mann theater & Suncoast Arena. 10 miles to Fort Myers Beach. 17 miles to Sanibel Island . 8 miles to Downtown Fort Myers and just 15 miles to the SWF International Airport. 2 parking spaces.
Indoor spacesKitchenHospitality

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!
KitchenIndoor spacesBathroom

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.
KitchenIndoor spacesOutdoor spaces

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
Indoor spacesFamilyComfort

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.
KitchenFamilyWalkability

Modern City Loft in Downtown River District
Welcome to Gun-Loft, a custom-designed modern sanctuary in the Downtown River District. This expansive 3500 square foot city loft is tailored for those seeking to embrace the cosmopolitan lifestyle, with the perfect blend of urban luxury and cultural richness. Whether it's a leisurely stroll to the Edison Ford Home, an exciting night out, or a culinary adventure in the restaurants nearby, Gun-Loft offers an unparalleled experience in the city's most coveted location.
KitchenFamilyPets

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.
FamilyKitchenAccess

SWFL: Lake McGregor Home - Entire Home! 3B/2B
Our home is in a quiet, safe neighborhood perfect for remote work, family getaways, or long-term stays in a kid-friendly environment. Spacious & Fully Equipped: 3 bedrooms • 2 bathrooms • Full kitchen • Washer/dryer • 2-car parking • WiFi • Smart TV • Beach gear available (Cable/streaming not included). Prime Location: 10 miles from Fort Myers Beach, 7 mi from Downtown, and a 7-min walk to Publix, Walmart, and restaurants. RSW Airport is a 20-min drive.
KitchenFamilyLocation

“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.
KitchenFamilyNearby

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.
FamilyIndoor spacesGetting around

Still available for Jan, Feb, March 2027
This well-maintained 4-bedroom, 3-bathroom home is thoughtfully furnished to meet all your needs. The location is a standout feature—just off US-41 and only minutes away from top restaurants, shopping malls, parks, and more. Don’t miss the inviting outdoor area, complete with a private pool and a fully fenced backyard—perfect for relaxing or entertaining. 🌴
Indoor spacesKitchenCheck-in
Popular amenities for Cypress Lake family-friendly rentals
Family-friendly home rentals with a hot tub

Luxury Riverfront Retreat • Pool & Spa • 60ft Dock
KitchenIndoor spacesCondition

Lanai Pool Home w/ Spillover Spa Near Beaches
KitchenFamilyQuiet

Serene Modern Oasis | Private Pool in Fort Myers
Indoor spacesKitchenLocation

Lowest Prices of Year-5 min to Town, Pet Friendly
FamilyKitchenHiking

Heated Pool & Game Room Waterfront Family Retreat
Indoor spacesFamilyBathroom

Luxury Waterfront Home/Hot Tub/BBQ | 8 Guests
Indoor spacesFamilyView

Waterfront Oasis w/ Heated Pool, Spa & Boat Dock
Indoor spacesKitchenGetting around

Experience of a lifetime
Indoor spacesFamilyOutdoor spaces
Family- and pet-friendly home rentals

Luxury Canal Villa•Heated Pool•Dock•Arcade•Kayaks
Indoor spacesFamilyShared spaces

Mini Golf • Heated Pool • Near Beach Prime
KitchenIndoor spacesPool

Water View villa in Fort Myers(B)
FamilyIndoor spacesDecor

Waterfront villa w/ heated pool & lake view.
FamilyKitchenNearby

Renovated 4/4 with Fishing, Pool, Boating, Beach
Indoor spacesKitchenSleep quality

Impulse 25 Beach Cottage
KitchenIndoor spacesDecor

Paradise on Estero Bay
Indoor spacesKitchenHospitality

Lakeview Oasis- Condo Near Sanibel/Ft Myers Beach
KitchenIndoor spacesParking
Family-friendly home rentals with a pool

Bonaire Grand Luxury Villa
FamilyIndoor spacesLaundry

Luxury Riverfront Estate & Pool
KitchenCleanlinessAccess

Intervillas Florida - Laguna Villa
FamilyKitchenView

Florida Vacation-Fort Myers-Pool-Gated Community
FamilyIndoor spacesComfort

NEW Coastal, Eclectic, Pool & Bikes, Sleeps 9
KitchenFamilyLayout

Villa510~3 En-Suites~Gulf Access, Heated spa~pool
KitchenFamilyHot tub

Casa Del Sol
FamilyKitchenWalkability

LUX Villa w/ Private Salt Water Pool, Lanai, Canal
KitchenIndoor spacesAccuracy
When is the best time to visit Cypress Lake?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | G$38,708 GYD | G$40,801 GYD | G$41,010 GYD | G$37,453 GYD | G$29,711 GYD | G$28,665 GYD | G$27,200 GYD | G$27,200 GYD | G$26,991 GYD | G$28,665 GYD | G$31,594 GYD | G$34,314 GYD |
| 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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