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, 142 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

KitchenIndoor spacesQuiet

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

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.

FamilyKitchenAmenities

Apartment in Cypress Lake

4.9 out of 5 average rating, 149 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.

KitchenIndoor spacesQuiet

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.

FamilyKitchenGrill

5 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 spacesFamilyBeach

4.97 out of 5 average rating, 29 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 spacesKitchenComfort

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, 107 reviews

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!

FamilyIndoor spacesPets

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.

KitchenIndoor spacesGetting around

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.

KitchenFamilyCondition

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.

Indoor spacesKitchenParks

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

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!

Indoor spacesKitchenLaundry

The peaceful pool area is enclosed by a screen canopy, featuring a heated lagoon-style pool. Sun loungers are arranged around the pool deck, and lush greenery is visible in the background, enhancing the serene environment. Blue skies complete the inviting atmosphere.

5 out of 5 average rating, 117 reviews

Relaxing Pool Home | Bikes | Prime SE Location

Relax in this bright 3BR/2BA home in a quiet SE Cape Coral neighborhood. Just minutes from beaches, Fort Myers, shops, and dining. Enjoy a private lagoon-style pool (heated in winter), a clean modern interior, and a calm, inviting atmosphere. Includes bikes, beach gear, garage access, and a pack ’n play—perfect for a comfortable and convenient Florida getaway.

Indoor spacesFamilyBackyard

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

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 out of 5 average rating, 102 reviews

Luxury Riverfront Retreat • Pool & Spa • 60ft Dock

Indoor spacesKitchenHot tub

5 out of 5 average rating, 4 reviews

Home in Iona

Lanai Pool Home w/ Spillover Spa Near Beaches

KitchenFamilyQuiet

An inviting pool area is surrounded by a screened enclosure, allowing natural light to illuminate the sparkling water. Comfortable lounge chairs are positioned alongside, while a dining space with a table and chairs is visible in the background, enhancing the outdoor experience.

5 out of 5 average rating, 52 reviews

Serene Modern Oasis | Private Pool in Fort Myers

Indoor spacesFamilyNearby

4.97 out of 5 average rating, 134 reviews

An outdoor dining area features a wooden table surrounded by several chairs, set against a backdrop of a vibrant sunset. The pool and landscaped yard are visible through expansive glass panels, while ceiling fans provide a cooling breeze.

Villa in Cape Coral

Dream Villa with Private Pool/Spa

FamilyKitchenDecor

5 out of 5 average rating, 6 reviews

Villa in Cape Coral

Seaside Villa Southern Belle - Southeast Paradise

Indoor spacesKitchenNearby

4.95 out of 5 average rating, 86 reviews

Home in Iona

Seahorse guesthouse Entire house close toSanibel

FamilyIndoor spacesHot tub

A screened outdoor space features a dining table with six chairs shaded by a fan. A private pool and spa, surrounded by lush greenery, are visible in the background, alongside two lounge chairs. Ample natural light filters through the enclosure.

4.97 out of 5 average rating, 135 reviews

Private Home w/ Heated SPA&Pool and Screened Lanai

FamilyKitchenBathroom

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

FamilyKitchenSleep quality

Family- and pet-friendly home rentals

A covered outdoor space features a cozy seating area with a dark wicker couch and light blue cushions. A patterned rug lies beneath, with lounge chairs arranged nearby. A swimming pool is visible through the screened enclosure, alongside landscaped greenery and a clear sky.

5 out of 5 average rating, 40 reviews

3 br | 3 ba | htd pool | Gulf Access | Paradise

KitchenFamilyBathroom

4.95 out of 5 average rating, 21 reviews

Mini Golf • Heated Pool • Near Beach Prime

FamilyIndoor spacesHospitality

5 out of 5 average rating, 4 reviews

Royal Palm Oasis with Private Pool in Cape Coral

KitchenIndoor spacesComfort

4.95 out of 5 average rating, 20 reviews

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

FamilyKitchenGetting around

4.67 out of 5 average rating, 55 reviews

The exterior of the villa features a light-colored façade with a sloped roof and a well-maintained lawn adorned with tropical plants. A driveway leads up to a garage on one side, while a double entrance door provides access to the home.

Cottage in Cape Coral

Villa The Island Hideaway 2

KitchenIndoor spacesBeach

A covered lanai showcases a sparkling pool with a jacuzzi beside it. Expansive glass panels reveal stunning sunset views over the water, while palm trees frame the scene. A modern gas grill and seating area create an inviting space for relaxation and outdoor dining.

5 out of 5 average rating, 7 reviews

Intervillas Florida - Laguna Villa

KitchenFamilyQuiet

5 out of 5 average rating, 7 reviews

Townhouse in Fort Myers

Lakeview Oasis- Condo Near Sanibel/Ft Myers Beach

FamilyIndoor spacesLong stay

4.92 out of 5 average rating, 25 reviews

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

FamilyIndoor spacesComfort

Family-friendly home rentals with a pool

4.67 out of 5 average rating, 3 reviews

Luxury Riverfront Estate & Pool

KitchenViewHospitality

4.97 out of 5 average rating, 70 reviews

A spacious living area is defined by a soft area rug and wooden flooring. Furniture includes a light blue couch, white dining chairs, and a dining table set. Natural light filters through large sliding doors leading to a balcony, with decorative artwork enhancing the walls.

Condo in Fort Myers

Spacious clean condo

KitchenIndoor spacesCondition

5 out of 5 average rating, 28 reviews

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

Indoor spacesFamilyAccuracy

5 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

KitchenFamilyAccuracy

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

Indoor spacesFamilyLayout

5 out of 5 average rating, 33 reviews

Riverview@EndPoint -Sunrises+Sunsets - Heat Pool

Indoor spacesKitchenRiver

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 out of 5 average rating, 27 reviews

Casa Del Sol

FamilyKitchenNearby

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.