Family-friendly holiday 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, 144 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

Apartment in Cypress Lake

Prime Location w/ Private Patio + Outdoor Kitchen

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.

4.9 out of 5 average rating, 154 reviews

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, 115 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!

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, 163 reviews

Paradise on Estero Bay

Welcome to Mullock Creek a Boater's dream! Southwest views boasting breathtaking sunsets overlooking gulf access canal from your spacious backyard, just minutes away from shopping and dining at Coconut Point, and Gulf Coast Town Center. This stunning Key West Style home has been beautifully maintained and updated offering a lovely front entrance, fully equipped kitchen, spacious Living Room, dining room, Wi-Fi, private driveway with access to the open garage, fully furnished and private pool.

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.

4.99 out of 5 average rating, 191 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!!

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.

4.97 out of 5 average rating, 34 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.

A comfortably appointed living area features a light-colored tufted sofa adorned with decorative cushions. A dark coffee table occupies the center of the space, which is illuminated by a ceiling light. In the background, a glimpse of the kitchen is visible.

4.94 out of 5 average rating, 223 reviews

Cottage between Sanibel and Edison / Ford Estate

This is the ultimate getaway for our guests. Yes…. you’re going to have an entire house for yourself . Feel free to enjoy 2 bedroom / 2 bathroom house with a Florida room, plus outside patio with gazebo(BBQ) and large back yard. Our newly renovated retreat is in the perfect location that is close to the beach, near all the best restaurants, and has all the amenities you will need for a breezy family vacation. Free L2 EV charging in the garage! Cleaning fee only $49.

4.95 out of 5 average rating, 405 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.

A welcoming kitchen and dining area features a round wooden table surrounded by stylish white chairs. Brightly colored flowers are displayed in a vase on the table. The kitchen, equipped with modern appliances, is visible in the background, complemented by light-toned walls and flooring.

4.92 out of 5 average rating, 125 reviews

SWFL: Lake McGregor House - 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.

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, 326 reviews

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.

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, 245 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.

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

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, 110 reviews

Serene Pool & Spa Home near Beaches & Downtown

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, 104 reviews

Luxury Riverfront Retreat • Pool & Spa • 60ft Dock

A spacious gazebo is shown framing a hot tub, with surrounding patio space visible. The backdrop includes a well-maintained lawn and a second gazebo, providing an inviting outdoor atmosphere. Soft lighting is featured, adding to the serene setting.

4.99 out of 5 average rating, 142 reviews

A peaceful waterfront scene captures the private dock extending into calm waters. Surrounding homes exhibit tropical landscaping with palm trees, while boats are secured at the docks. The cover on the boat lift provides shade, enhancing the environment for outdoor activities.

4.97 out of 5 average rating, 185 reviews

“Cape Paradise”Waterfront.GulfAcc.Jcuzi.Heat Pool.

4.87 out of 5 average rating, 115 reviews

The exterior of the villa showcases a modern architectural design, highlighted by a grand entrance with large arched windows and a tiled roof. Lush greenery and palm trees complement the manicured lawn, while a paved driveway leads to an expansive garage.

Villa in Cape Coral

"Coral Point Villa" - Gulf access /Sailboat access

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, 104 reviews

Modern City Loft in Downtown River District

4.99 out of 5 average rating, 116 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

5.0 out of 5 average rating, 42 reviews

Waterfront Oasis w/ Heated Pool, Spa & Boat Dock

Family- and pet-friendly home rentals

4.9 out of 5 average rating, 129 reviews

Cape Serenity- Luxury Waterfront Residence

A fenced-in screened patio encloses the outdoor pool, showcasing clear blue water under a bright sky. Lush greenery lines the background, enhancing the tranquil outdoor space while the pool ladders offer easy access for enjoyment.

4.9 out of 5 average rating, 40 reviews

Luxury Oasis with Private Pool!

Superhost

4.76 out of 5 average rating, 38 reviews

Palms and Paradise

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.

4.94 out of 5 average rating, 79 reviews

Sunny Coastal Getaway w/ Heated Pool Near Beaches

4.92 out of 5 average rating, 26 reviews

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

A spacious living area features a comfortable sofa adorned with decorative pillows. A coffee table and ottoman provide additional seating. Light from a nearby lamp creates a warm ambiance, while a colorful painting adds a focal point to the wall. A dining area is visible in the background.

4.94 out of 5 average rating, 17 reviews

Water View villa in Fort Myers（A）

4.95 out of 5 average rating, 22 reviews

Renovated 4/4 with Fishing, Pool, Boating, Beach

4.96 out of 5 average rating, 25 reviews

Mini Golf • Heated Pool • Near Beach Prime

Family-friendly home rentals with a pool

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, 57 reviews

Mermaids Cove, don't miss this listing!

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, 57 reviews

Ocean Blue - Luxurious 4BR home w/heated pool

4.94 out of 5 average rating, 16 reviews

4BR Waterfront Home w/ Heated Pool & Private Dock

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

Superhost

4.87 out of 5 average rating, 90 reviews

Waterfront Pool Home/Sailboat Access & Dock

5.0 out of 5 average rating, 19 reviews

A comfortable living area is depicted, featuring a light gray sectional sofa and a stylish coffee table. A round mirror and decorative wall art enhance the space. The open kitchen and dining area are subtly visible in the background, creating a welcoming environment.

Townhouse in Fort Myers

Florida Vacation-Fort Myers-Pool-Gated Community

4.91 out of 5 average rating, 34 reviews

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