Family-friendly vacation rentals in Summerland Key

Find and book unique family-friendly homes on Airbnb

Top-rated family-friendly rentals in Summerland Key

Guests agree: these family-friendly homes are highly rated for location, cleanliness, and more.

0 of 0 items showing

1 of 3 pages

Top guest favorite

A bright and welcoming living space features a galley kitchen with a counter and two stools. The refrigerator is visible along with colorful walls in shades of yellow and coral. A TV unit stands nearby, and a red sofa adds a pop of color to the cozy area.

Apartment in Key West

4.98 out of 5 average rating, 496 reviews

Bella Vita: 1B/1B Condo for 2 Just Steps off Duval

1B/1B condo located in Old Town less than 1/2 block from Duval St. & a couple blocks from the Southernmost Point, Hemingway House & many other Key West attractions. Bella Vita accommodates 2 adults only and features a large porch with chairs & table, living room with leather sofa, galley kitchen with bar seating, king-size bed with Tempurpedic mattress, desk area, bathroom with large walk-in shower, wi-fi, sound machine, 2 Smart TVs, DVD players & BlueTooth stereo system with CD player & radio.

Guest favorite

A well-appointed kitchen area features stainless steel appliances and granite countertops. A doorway leads to a light-filled hallway, which connects to two bedrooms. Decorative fishing-themed artwork and coastal colors create a refreshing atmosphere.

Villa in Marathon

4.95 out of 5 average rating, 135 reviews

Private 4/3 Pool Heater/Dock/Kayaks/Bikes,etc

Wake up to breathtaking water views at our 4-bedroom, 3-bathroom villa. Enjoy the 1800 sq ft layout, fully equipped kitchen w/stainless steel appliances, and granite countertops. Sleeps 10 with memory foam beds. Outside, relax by your private heated pool (winter) and tiki-shaded area. Fish from the 32' dock or use the BBQ gas grill. Includes 2 kayaks, 2 paddleboards, and 4 adult bikes for a 5-minute ride to Sombrero Beach. Exterior cameras for security. Vacation License #VACA-22-40. Book now!

Superhost

A scenic pool area features colorful adirondack chairs overlooking the calm waters of the bay. A thatched-roof tiki hut provides shade, while a paved patio surrounds the pool, with the serene horizon merging with the sky in the background.

Home in Cudjoe Key

4.91 out of 5 average rating, 110 reviews

Sunrise Beach Escape

For your next vacation, come stay in this resort home, where you'll enjoy a cocktail at sunset alongside the Cudjoe bay overlooking the Atlantic Ocean. This beautiful and luxurious home is part of the Sunrise Beach Resort, an exclusive 11 home gated community overlooking the Atlantic Ocean & Cudjoe Bay. A community that is only 17 miles north of Key West. Make yourself at home in this tastefully decorated 1200 sq foot living space, which offers countless amenities such as kayaks and bikes.

Guest favorite

A private outdoor deck features a two-person Solana spa surrounded by lush greenery. A striped umbrella provides shade over a chair, while a towel hangs against a white fence. Natural light filters through the tropical plants, enhancing the tranquil atmosphere.

Home in Key West

4.97 out of 5 average rating, 251 reviews

Harrison's Hideaway-Sleeps up to 4, K & F Sl Sofa!

Historic Harrison's Hideaway is in an 1880's Cigar Maker's cottage renovated in 2010. It features a K size Pottery Barn memory foam bed, custom made full sleeper sofa, newly renovated kitchen with granite counter tops, 2 burner stove, under counter fridge/freezer, dishwasher, microwave, tumbled marble 2 person shower, private front deck with seating for 4 and 2 person Solana spa. Perfect for a couple or a family with children. Freshly painted a Caribbean blue with plantation shutters.

Guest favorite

A bright bathroom featuring two sinks with polished fixtures and a spacious vanity below. Above the sinks, two mirrors are framed elegantly. Soft lighting illuminates the room, which includes a toilet and a glass-enclosed shower. Cream-colored tiles enhance the clean and modern aesthetic.

Apartment in Key West

4.92 out of 5 average rating, 184 reviews

KW Luxury 2/2 Beachfront resort Tropical Oasis

1357 s f Luxury beachfront resort condo w/ all the amenities - beachfront heated Olympic pool, 3 lighted tennis courts, 20 man hot tub, tropical gardens, beach, saunas, Gym, BBQ Grills everything to make your vacation spectacular! You must be at least 25 years old to rent this property. This is a no animal rental due to extreme allergies of the owner. Thank you for understanding. Also there is discussion of spalling work in 2026 on balconies will firm dates as we get closer

Guest favorite

A private balcony is shown, featuring colorful patio chairs and vibrant tropical plants. The space is framed by white railings and light blue shutters, creating a fresh and inviting setting for relaxation.

Condo in Key West

4.89 out of 5 average rating, 224 reviews

Tropical Old Town Bungalow

Great Location, Close to Duval & Beach Welcome to paradise! This Tropical Old Town Bungalow is located perfectly between Key West’s best beaches and the best restaurants and nightlife! The rental unit sits right between the White Street Art Gallery District and the Historic District, which features some of Key West’s most historic homes and properties. Whether you are walking, riding bikes or grabbing a quick cab, no destination is too far from this conveniently located rental.

Guest favorite

A collage highlights an inviting outdoor space featuring a heated pool, hot tub, and two putting greens on lush lawn. The open living area showcases comfortable seating, light-colored furnishings, and ocean-themed decor. Exterior views reveal spacious patios and well-maintained landscaping under a colorful sunset.

Home in Marathon

4.95 out of 5 average rating, 131 reviews

Paradise - Pool, Hot tub, Mini Golf, Dockage, Fish

House suits multiple families with kids, groups of couples, small and large families, or solos. Home is easy to get to, easy to get inside and the neighborhood is very peaceful. Plenty to do around the island or on the water. 5 large bedrooms and 3 large bathrooms with an open living room and a fully stocked kitchen. We look forward to hosting you. Very Short Walking distance to Sweet Savannah's Ice Cream and Sweets Parlor

Top guest favorite

The entrance to the home is framed by lush greenery and colorful plants. A welcoming pathway leads to the front door, which features intricate wooden detailing. Bright flowers and palm trees enhance the tropical ambiance of the exterior.

Home in Marathon

4.94 out of 5 average rating, 185 reviews

Avail. Now! 70ft Dock, Close to Beach VACA23-16,

Enjoy the boutique decor of our large, spacious home. Our place is a short distance from Sombrero Beach, with bicycles available to ride there. Our property is on a wide and deep canal, with both ocean and gulf access. Our dock is 70 ft, so ideal place for large boats, or you can even bring 2 boats. Free parking, with space to park boat trailer. We include free passes to the Sea Turtle Hospital to guests.

Guest favorite

A tennis court is visible behind a large tree, with a lush green lawn surrounding it. The court is enclosed with a fence, and additional trees and shrubs are present in the vicinity, contributing to a natural landscape.

Apartment in Marathon

4.97 out of 5 average rating, 103 reviews

Beachfront Condo w/ Ocean Views in Marathon

Beautifully decorated 2nd floor end unit with stunning panoramic ocean views from the balcony, living room and master bedroom. Two bedrooms / two full bathrooms and washer and drier in unit. Full kitchen. Directly on the beach! Beach chairs, umbrellas and towels provided for you. Guests have access to the heated swimming pool, tennis court and beach. Master bedroom king-size memory foam mattress

Top guest favorite

A light-filled living area features a comfortable sofa paired with accent tables. Soft blue walls create a calming backdrop, while stylish decor elements, such as framed artwork and lamps, add character. A mirror reflects the space, enhancing its openness and inviting ambiance.

Condo in Key West

5 out of 5 average rating, 24 reviews

EYW Getaway

Relax with the whole family at this peaceful place to stay. Our two-bedroom two-bathroom condo with complete kitchen is located at Sunrise Suites Resort. Amenities include shared heated pool, hot tub, tennis court and a basic gym. Our condo is located 1mile from the airport, 1.5 miles from the beach and 3.5 miles from downtown Duval St.

Superhost

A spacious saltwater pool is surrounded by tropical palm trees and a lush landscape. Sun loungers with blue umbrellas are positioned along the pool's edge, providing shaded seating for relaxation. Light dances on the water's surface under clear blue skies.

Townhouse in Key West

4.93 out of 5 average rating, 217 reviews

Spotlessly clean 3 bedroom/3 bathroom family home

Great family home in the gated community of Coral Hammock, located just 10 minutes from the center of Key West. It boasts a saltwater pool just steps away from the property. Perfect for families or groups of mature adults. All renters must be 25 or over or with a parent/guardian.

0 of 0 items showing

What guests are saying

Villa Casa Cayo

4.9 out of 5 average rating, 20 reviews3 months ago

This home was just what my family needed for our vacation! We all loved relaxing in the outdoor living room surrounded by greenery. We also enjoyed swimming in the pool and kayaking through the canals and Boot Key. We made most of our meals due to dietary restrictions, and the kitchen here was adequate. The location in Marathon is excellent! It was just a 5-minute walk to Sombrero Beach, so we never had to worry about parking. We could easily drive to all the activities we wanted to do in the area, too.

Home in Marathon

What guests are saying

Old Town Suites - 2 Bedroom Suite #2

4.79 out of 5 average rating, 225 reviews1 month ago

Great place close to everything!! We decided against renting a car and I am so glad because everything was walkable. The AC worked great which we very much appreciated. The cuban restaurant downstairs and the CVS right across the street really made everything super convenient. We would definitely stay here again!

Apartment in Key West

What guests are saying

Henry's Piece of Paradise On The Ocean In Key West

4.84 out of 5 average rating, 37 reviews1 month ago

My daughters and I came from 3 different locales to spend a few days together at Henry's condo. We were very comfortable. The condo is stocked with kitchen utensils, beach towels and chairs, tvs, and a sound system. It was a bit chilly for the pool, but we enjoyed the community's hot tub and landscaped community area. Smathers Beach is a short walk away. Higgs Beach is also walkable and has plenty of parking. I wanted to try the snorkeling trail at Higgs, but it was a bit chilly for me. Still, February in Key West was a welcome relief from the 20 degree weather and snow I left behind! There was a lot of paperwork for an Airbnb ahead of arrival, but everything went great. Henry was always available, responsive, and helpful. We had a terrific reunion and enjoyed Key West.

Condo in Key West

1 of 12 pages