Family-friendly vacation rentals in Cypress Lake

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.

4.96 out of 5 average rating, 143 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

Indoor spacesKitchenPool

Apartment in Cypress Lake

4.9 out of 5 average rating, 150 reviews

“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.

KitchenFamilyBeach

A spacious screened lanai surrounds a shimmering pool, offering a relaxing environment. Colorful lounge chairs line the poolside, providing ample seating for guests. Lush greenery is visible beyond the screen, enhancing the private retreat ambiance of the outdoor area.

4.9 out of 5 average rating, 113 reviews

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 spacesLayout

4.97 out of 5 average rating, 156 reviews

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

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.

Indoor spacesFamilyWifi

5.0 out of 5 average rating, 15 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

Indoor spacesFamilyLocation

4.97 out of 5 average rating, 30 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.

Indoor spacesKitchenAmenities

An expansive open kitchen and dining area showcases sleek white cabinetry and a large kitchen island. Wooden barstools provide seating at the island, while contemporary lighting fixtures hang above. Large windows enhance the airy atmosphere, revealing a modern living space in the background.

4.99 out of 5 average rating, 103 reviews

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.

FamilyIndoor spacesAccuracy

4.95 out of 5 average rating, 402 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.

KitchenFamilyBreakfast

A bright living space is presented with light-colored walls and modern furnishings. A large television displays a vibrant underwater scene. A cozy blue chair and a gray sofa with patterned cushions provide seating, while a wooden coffee table holds decorative items. Natural light illuminates the area.

4.9 out of 5 average rating, 155 reviews

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.

FamilyIndoor spacesDecor

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.

4.98 out of 5 average rating, 244 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.

FamilyKitchenCheckout

4.91 out of 5 average rating, 190 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.

FamilyKitchenWalkability

4.9 out of 5 average rating, 160 reviews

A well-equipped kitchen features modern appliances, including a stainless steel refrigerator and microwave. Stylish pendant lights hang above a spacious island with a granite countertop. A fruit bowl adds a pop of color, while ample cabinetry provides storage space.

Home in Villas

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 spacesKitchenWifi

Popular amenities for Cypress Lake family-friendly rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Family-friendly home rentals with a hot tub

4.96 out of 5 average rating, 160 reviews

A refreshing heated saltwater swimming pool is surrounded by a screened enclosure, featuring two sun loungers partially submerged in water. An oversized teal umbrella provides shade, while a small floating tray holds drinks. The serene canal views are visible in the background.

Home in Pelican

Heated Pool & Game Room Waterfront Family Retreat

Indoor spacesKitchenView

A serene outdoor area features a private pool with a unique shape and a spa nearby. Sun loungers are positioned beside the pool, surrounded by lush tropical landscaping. A covered patio area is visible in the background, offering a shaded space for relaxation.

4.93 out of 5 average rating, 108 reviews

Serene Pool & Spa Home near Beaches & Downtown

FamilyIndoor spacesGrill

A screened-in lanai features a tranquil heated pool with a spa, surrounded by paver stones. The sunset reflects on the water, providing a picturesque backdrop. Palms sway gently in the breeze, enhancing the serene setting suitable for relaxation and enjoyment.

4.97 out of 5 average rating, 323 reviews

Dolphin beach house 2

FamilyKitchenRiver

An inviting screened-in patio features a large heated swimming pool surrounded by lounge chairs. Sculptures adorn the sides of the pool, and lush greenery is visible through the expansive windows, offering tranquil views of the outdoors and tranquil ambiance.

5.0 out of 5 average rating, 102 reviews

Luxury Riverfront Retreat • Pool & Spa • 60ft Dock

FamilyIndoor spacesShared spaces

4.99 out of 5 average rating, 114 reviews

A sunlit pool area is framed by palm trees, with views of the canal and neighboring homes in the background. Comfortable loungers are positioned along the poolside, inviting relaxation amidst the tranquil waterfront setting.

Home in Fort Myers Beach

Paradise on canal minutes to Ft Myers Beach/Gulf

Indoor spacesKitchenValue

4.93 out of 5 average rating, 134 reviews

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 Iona

Experience of a lifetime

Indoor spacesKitchenValue

The backyard features a hot tub in the foreground, with a clear view of a pool in the background. Colorful adirondack chairs are arranged around the pool area, and a spacious house is visible with a screened porch. String lights are seen overhead, enhancing the outdoor ambiance.

4.98 out of 5 average rating, 133 reviews

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

KitchenFamilyCheckout

4.95 out of 5 average rating, 100 reviews

Luxury Waterfront Home/Hot Tub/BBQ | 8 Guests

Indoor spacesFamilyAmenities

Family- and pet-friendly home rentals

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.

4.94 out of 5 average rating, 162 reviews

Paradise on Estero Bay

FamilyKitchenGrill

4.94 out of 5 average rating, 188 reviews

Home in Pelican

Waterfront villa w/ heated pool & lake view.

KitchenIndoor spacesCheckout

A heated pool with a clear blue surface is surrounded by a cozy patio area. Lounge chairs provide a space for relaxation, while lush palm trees and vibrant greenery frame the serene waterfront view. A shaded umbrella offers a spot to enjoy the outdoors.

4.99 out of 5 average rating, 160 reviews

Luxury Canal Villa•Heated Pool•Dock•Arcade•Kayaks

FamilyIndoor spacesView

The living area features a sectional sofa with decorative pillows, a circular coffee table, and a plush armchair. A large mirror reflects light, while a ceiling fan is visible above. A textured area rug in cool tones anchors the space, which leads to the dining area in the background.

4.89 out of 5 average rating, 9 reviews

Water View villa in Fort Myers（B）

FamilyIndoor spacesView

4.92 out of 5 average rating, 25 reviews

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

KitchenFamilyBeach

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.

4.93 out of 5 average rating, 76 reviews

Sunny Coastal Getaway w/ Heated Pool Near Beaches

Indoor spacesKitchenComfort

4.95 out of 5 average rating, 22 reviews

Mini Golf • Heated Pool • Near Beach Prime

FamilyIndoor spacesComfort

5.0 out of 5 average rating, 7 reviews

Townhouse in Fort Myers

Lakeview Oasis- Condo Near Sanibel/Ft Myers Beach

FamilyKitchenLocation

Family-friendly home rentals with a pool

4.99 out of 5 average rating, 262 reviews

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 Pelican

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

FamilyIndoor spacesOutdoor spaces

An outdoor kitchen area features a thatched roof and a stone counter with an assortment of vibrant destination signs. Comfortable chairs are arranged for seating, and a wall-mounted television is visible, surrounded by lush greenery and soft lighting.

5.0 out of 5 average rating, 56 reviews

Ocean Blue - Luxurious 4BR home w/heated pool

KitchenFamilyHospitality

Superhost

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.

4.84 out of 5 average rating, 25 reviews

NEW Coastal, Eclectic, Pool & Bikes, Sleeps 9

KitchenFamilyPool

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.

4.95 out of 5 average rating, 56 reviews

Mermaids Cove, don't miss this listing!

Indoor spacesFamilyAmenities

The exterior of the home features a well-maintained façade with a combination of light brown stucco and stone accents. Lush greenery surrounds the entrance, including palm trees and flowering plants, complemented by a circular driveway and a clear blue sky overhead.

5.0 out of 5 average rating, 27 reviews

Casa Del Sol

FamilyIndoor spacesAccess

4.92 out of 5 average rating, 13 reviews

Villa in Iona

Bonaire Grand Luxury Villa

Indoor spacesKitchenView

5.0 out of 5 average rating, 9 reviews

Waterfront with Saltwater Pool, Sauna, Cold Plunge

KitchenFamilyHospitality

A spacious heated pool is enclosed by a screened patio, allowing sunlight to reflect off the clear water. A bright pink inflatable flamingo floats on the surface. Lush greenery surrounds the pool area, providing a serene outdoor space for relaxation.