Family-friendly holiday rentals in Cypress Lake

4.99 out of 5 average rating, 113 reviews

An outdoor area features a well-maintained gravel landscape, framed by lush greenery and palm trees. A round table with four vibrant red chairs offers a place for gathering, set against a backdrop of a pastel-colored guest house with a distinctive turquoise door and awning.

Guesthouse in Fort Myers

Private guest house—minutes to the best beaches!

Experience the charm of Fort Myers in this quaint, private guest house located in the historic district. Perfectly situated near Fort Myers Beach (12 miles), Sanibel Island (16 miles), downtown (4 miles), some of the areas best restaurants (some even walking distance), grocery stores, & convenience stores. Easy access to Southwest Florida International Airport & FGCU. Uber and Lyft are easy access. The neighborhood is peaceful, safe, & walk friendly. Book now for a convenient and memorable stay.

4.98 out of 5 average rating, 187 reviews

The modern kitchen is equipped with white cabinetry and stainless-steel appliances. A circular table with seating for four is positioned near a large glass sliding door that allows natural light and offers views of the outdoor space. A ceiling fan adds comfort to the room.

Guesthouse in Fort Myers

Waterfront Hideaway

This picturesque Airbnb is a hidden gem nestled along a canal, one minute boat ride to the Caloosahatchee River. The living room, bathed in natural light is perfect for taking in the scenic views. The spacious bedroom has a king-size bed, ensuring a night of blissful rest. The full kitchen is equipped with all modern appliances. Close to Sanibel & Fort Myers Beach. Bring your boat & dock it on the seawall, ready to set sail whenever your heart desires. Book now - your coastal paradise awaits!

4.82 out of 5 average rating, 110 reviews

A compact kitchen is equipped with modern appliances, including a coffee maker, microwave, and refrigerator. A granite countertop offers ample workspace, while cabinets provide storage. Soft blue lighting from a sign enhances the atmosphere, and a small dining table is positioned nearby.

Guesthouse in Cape Coral

Perfect Place for your Vacations

This Guesthouse has everything you need for your vacation, it is central located, in a peaceful and safe neighborhood and have a very well distributed space. Its located few minutes from the Caloosahatche River and the beautiful beaches of the Gulf of Mexico, it includes bicycles, kayaks, umbrella, beach chairs, fishing rods and other items that will enhance your vacation. It is also very close to highly recommended restaurants, famous shops (walmart,Publix, McDonald) and other essential places.

4.88 out of 5 average rating, 100 reviews

Apartment in Fort Myers

Prime location, very private, nice & spacious

The best location, period. This very quiet and private one bedroom apartment has a paved & shaded parking . To ensure a long night rest there are black out rolls on windows. Private courtyard with Gas grill & side burner. 1 block from Publix supermarket. Walk to FSW State College. Walk to Barbara B Mann theater or Suncoast Arena. 10 miles to Fort Myers Beach. 17 miles to Sanibel Island beaches. 8 miles to Downtown Fort Myers and just 15 miles to the SWF International Airport. 2 parking spaces.

4.97 out of 5 average rating, 133 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.

A spacious living area is filled with natural light, featuring a large sectional sofa and a media console with a flat-screen TV. The open layout connects to a dining area with a round table and modern chairs, leading into a well-equipped kitchen with warm wooden cabinets.

4.98 out of 5 average rating, 110 reviews

Hot Tub/ King Bed - Cozy Home in Cape Coral!

Welcome to our Cozy Cape Coral Getaway! Step into a spacious, open layout that welcomes all families & friends with open arms! Nestled in a perfect central location, our place was designed with your convenience in mind! Whether you're whipping up delicious meals in the full kitchen, enjoying quality time in the game-filled living space, or hanging out in the jacuzzi/ private fenced backyard. We are committed to transforming every moment here into unforgettable memories! *PET FRIENDLY*

4.96 out of 5 average rating, 136 reviews

A bright dining area is highlighted by a round wooden table surrounded by blue chairs. Natural light fills the space through large sliding glass doors, showcasing a peaceful lake view framed by trees. A television displaying a beach scene adds to the coastal ambiance.

Home in Fort Myers Beach

Charming Lake View Home, Close to 3 Beaches!

"Come relax by Florida's best beaches and sunsets—no damage from Hurricane Milton, and power/internet are on! This beach-style vacation home is minutes from Ft. Myers Beach and 15 minutes from Sanibel. You'll be spoiled by beach choices and amenities that make you feel like you're in paradise. In the evening, hop on the trolley to watch the sunset, enjoy cocktails, and the best beachside seafood. Just bring your sunglasses & flip flops. Forgot something? Shops are a 5-min walk."

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, 187 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.

4.94 out of 5 average rating, 356 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 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.

4.91 out of 5 average rating, 119 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.

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, 224 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.

4.91 out of 5 average rating, 195 reviews

A screened-in pool area is visible, featuring a clear blue pool with a shallow entry. Sunlight reflects off the water, and a few chairs are arranged around the pool. A shaded outdoor kitchenette is in the background, with a fenced yard beyond.

Apartment in Cape Coral

Private Apartment with sunny pool

One-bedroom plus den apartment attached to the main house with private entrance. The apartment has a small kitchenette for basic meal preparation. A large pool is right outside your door! Come relax by the pool & cool off on a hot day. The pool is for your private use. We have a gas BBQ grill located in the fenced yard for your use. Ft. Myers Beach 35 min away Sanibel Beach 45 min away Naples Beaches 60 min away

Popular amenities for Cypress Lake family-friendly rentals

Kitchen

Wi-Fi

Pool

Free parking on premises

Air conditioning

Family-friendly home rentals with a hot tub

4.95 out of 5 average rating, 85 reviews

A heated pool and spa are visible, surrounded by a spacious pool deck. A screened lanai adjacent to the entrance of the unit provides additional lounging space. Lush greenery is seen near the building, contributing to a tranquil outdoor environment.

Apartment in Cape Coral

SeaTurtle Apt 3 -Tudor Getaway Resort-Heated Pool

A private hot tub bubbles gently within a screened patio, adjacent to a swimming pool. Comfortable outdoor seating is visible, with a view of the surrounding greenery and a nearby television for entertainment. Ceiling fans provide ventilation in the warm atmosphere.

5 out of 5 average rating, 5 reviews

Private pool 4 bedroom vacation home

A single-story home is featured, displaying a well-maintained lawn and a paved driveway. Lush palm trees and flowering plants are visible, enhancing the inviting exterior. The home has a tiled roof and large windows, allowing for natural light. A garage door is located to the right.

5 out of 5 average rating, 22 reviews

Robin's Nest on a Canal with River and Gulf access

A cozy living area contains a comfortable beige sofa and a black reclining chair. A white coffee table is situated in front of the sofa. Natural light filters through the window curtains, illuminating the space. A ceiling fan and wall-mounted TV enhance the inviting atmosphere.

5 out of 5 average rating, 16 reviews

Impulse 25 Beach Cottage

A relaxing outdoor jacuzzi is framed by sheer turquoise drapes, offering a sense of privacy. The bubbling water is visible, creating a soothing atmosphere. A patio chair is situated nearby, and a glimpse of the house is seen in the background through the drapes.

5 out of 5 average rating, 57 reviews

Seahorse guesthouse Entire house close toSanibel

A spacious waterfront home is surrounded by lush greenery and palm trees. The Mediterranean-inspired architecture features a red-tiled roof and large front entrance, along with a neatly paved driveway leading to a two-car garage. Bright blue skies provide a clear backdrop.

4.97 out of 5 average rating, 115 reviews

Gone Coastal!! Spa+Heated Pool Amenities Galore!

4.67 out of 5 average rating, 6 reviews

A spacious living area features a large blue sectional sofa complemented by a decorative wall hanging. Natural light floods through multi-paned windows, illuminating light-colored walls. A unique armchair adds to the aesthetic, with a small wooden side table positioned nearby.

Condo in Fort Myers

Lovely 2-Bedroom w/pool and 5 minutes from beach

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.

4.91 out of 5 average rating, 101 reviews

Experience of a lifetime

Family- and pet-friendly home rentals

A spacious heated pool invites relaxation, bordered by lounge chairs and a vibrant red umbrella offering shade. The clear water reflects the surrounding greenery, while expansive water views showcase the peaceful canal, enhancing the tranquil outdoor setting.

4.99 out of 5 average rating, 134 reviews

Luxury Waterfront Villa• Heated Pool• Dock• Kayaks

4.83 out of 5 average rating, 115 reviews

A modern kitchen features light grey cabinetry and stainless steel appliances, including a coffee maker and microwave. Natural light illuminates the space through a window above the sink, which is complemented by a sleek blue faucet. The countertop provides ample workspace.

Condo in Fort Myers

Cozy Coastal Escape. Close to FMB and Sanibel

The inviting saltwater pool is surrounded by lush tropical plants and trees, including a prominent palm. A natural rock waterfall feature enhances the serene setting under a bright blue sky, with fluffy white clouds adding to the tranquil atmosphere.

4.86 out of 5 average rating, 132 reviews

Amazing Location, Walk to Downtown! Heated Pool!

The screened-in pool area features a sparkling swimming pool surrounded by a spacious deck. Natural light filters through the mesh enclosure, reflecting off the water. Outdoor seating is provided by a small table and chairs, with trees framing the serene backdrop.

4.95 out of 5 average rating, 129 reviews

Waterfront Home w/ Pool. Minutes to Sanibel

5 out of 5 average rating, 131 reviews

A spacious outdoor area features a heated pool surrounded by a paved deck. Comfortable lounge chairs and an umbrella are positioned nearby, offering a relaxing space. The backyard is framed by greenery and a fenced perimeter, ensuring privacy and a serene ambiance.

Villa in Cape Coral

Casa Capri | Heated Pool | No Service Fee

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, 31 reviews

Luxury Oasis with Private Pool!

4.92 out of 5 average rating, 136 reviews

A rustic wooden cabin is nestled within a lush green landscape, surrounded by trees. Soft lighting illuminates the entrance, and a welcoming staircase leads to the door. Vibrant plants and flowers enhance the peaceful outdoor setting, creating a harmonious connection with nature.

Cabin in Fort Myers

Luxury Spacious Cabin Nature Preserve Fort Myers

4.9 out of 5 average rating, 157 reviews

Dive into Luxury: Stunning Tropical Home & Pool

Family-friendly home rentals with a pool

An inviting pool area is enclosed by a screened lanai, featuring a gently curved pool with clear water. Surrounding the pool, a spacious patio is laid with decorative pavers, while comfortable seating is visible in the shaded corner, offering a relaxing space for gatherings.

4.91 out of 5 average rating, 67 reviews

Pool Paradise Central - Cozy 3 BR home w/ lanai

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, 21 reviews

Serene Modern Oasis | Private Pool in Fort Myers

An outdoor area features a private heated pool surrounded by a spacious deck. Soft lighting creates a relaxing ambiance, while lounge chairs are positioned near the water. Several inflatable pool floats rest on the surface of the water, contributing to a welcoming space for relaxation.

4.93 out of 5 average rating, 96 reviews

Private Pool 3/2 home, between Ft Myers and Beach!

A private, screened-in pool area is presented, surrounded by a spacious deck with lounge chairs. The pool reflects blue skies above, while the adjoining living space features patio doors. Nearby, a dining table is seen under the cover of the lanai.

4.98 out of 5 average rating, 117 reviews

The Dolphin Villa Cape Coral Pool Home Sleeps 8

5 out of 5 average rating, 4 reviews

Apartment in Fort Myers

Luxury II

A clear blue pool is surrounded by a spacious patio, featuring comfortable loungers partially immersed in the water. The inviting outdoor space overlooks the serene canal, while the covered lanai offers additional seating options. Lush palm trees sway gently in the background under a bright sky.

4.97 out of 5 average rating, 124 reviews

Boater’s Paradise-Stunning Sunsets! Games Room!

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.

5 out of 5 average rating, 10 reviews

NEW Coastal, Eclectic, Pool & Bikes, Sleeps 9