Family-friendly vacation rentals in Stock Island

Find and book unique family-friendly homes on Airbnb

Top-rated family-friendly rentals in Stock Island

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

0 of 0 items showing

1 of 3 pages

Guest favorite

Apartment in Key West

4.98 out of 5 average rating, 450 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.

Apr 26 – May 3

G$69,639 GYD per night

Superhost

Condo in Key West

5.0 out of 5 average rating, 12 reviews

Cielo Azul @ Beach Club - Oceanfront Condo

FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 30 days prior to your arrival! ** Last Key Realty requires a credit card on file for all reservations. ** This freshly renovated oceanfront condo has been meticulously designed and furnished to a very high standard. No expense was spared to make CIELO AZUL a unique tropical oasis. The sleek, upscale furniture is complemented with splashes of color throughout the home. The ocean front balcony runs the entire width of the

Aug 10 – 17

G$147,565 GYD per night

Guest favorite

Townhouse in Duck Key

4.98 out of 5 average rating, 141 reviews

3Bd 3Ba Cottage/Village at Hawks Cay/Ocean Views

Our Cottage is located between Islamorada and Marathon Key on Duck Key at the Village of Hawks Cay; one of the most desirable locations in the Florida Keys. This is at Mile Marker 61. With ocean views, high end finishes, comfy beds and plenty to do in the surrounding areas, the Cottage offers something for everyone. The outdoor green space overlooking the water is gorgeous. Sunsets are amazing right off the screened in lanai. We hope to host you as our guest in the beautiful Florida Keys.

Jan 10 – 17

G$144,081 GYD per night

Superhost

Home in Cudjoe Key

4.9 out of 5 average rating, 104 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.

Sep 19 – 26

G$83,555 GYD per night

Guest favorite

Home in Key West

4.97 out of 5 average rating, 206 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.

Sep 16 – 23

G$83,138 GYD per night

Guest favorite

Home in Marathon

4.93 out of 5 average rating, 169 reviews

Beach, 70ft Dock, Entire Home, VACA-23-16

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.

Oct 3 – 10

G$61,122 GYD per night

Superhost

Apartment in Key West

4.89 out of 5 average rating, 136 reviews

Key West Beachside 1400sf, 2 Bedroom Condo

Welcome to our Key West Condo. This spacious well appointed 2 bedroom, 2 bath condo sleeps 6 and is next to the best beach on Key West. This condo is the perfect alternative to staying in a hotel. It gives you a true island experience. Great for Couples and Families We have a Website specific to our Condo where we offer special pricing, discounts and additional pictures Search-keywestbeachsidecondo

Oct 6 – 13

G$114,491 GYD per night

Superhost

Apartment in Key West

4.92 out of 5 average rating, 175 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

Sep 6 – 13

G$109,532 GYD per night

Guest favorite

Apartment in Key West

4.97 out of 5 average rating, 237 reviews

Poolside Truman Annex 2 Bed | Conch Life Condo

Cozy condo in the Truman Annex to fully experience the conch life. It is close to Fort Zachery Beach and State Park, Hemingway House, Mallory Square, and Duval Street. Location is perfect due to Island proximity to any event and occasion. My place is a great getaway for couples, solo adventurers, business travelers, and families (with kids).

Apr 14 – 21

G$153,702 GYD per night

Guest favorite

Apartment in Key West

4.94 out of 5 average rating, 359 reviews

Studio Blu - Key West, FL - Hip Studio in Old Town

Location, location, location! Situated in the heart of the Cuban district, steps from arguably the best 'con leche' in Key West, this Studio apartment is minutes from everything on the island. No cars are necessary, bikes & beach chairs are provided.

Sep 14 – 21

G$52,890 GYD per night

Superhost

Apartment in Key West

4.76 out of 5 average rating, 393 reviews

The Green House ❀ Garden

Unique and beautifully renewed apartment in the heart of Key West. Spacious bedroom with King Size bed and Walk-in Closet, large living room with pull-out sofa bed and kitchen. Take advantage of our unbeatable reopening prices and enjoy! ♡

Feb 25 – Mar 4

G$107,779 GYD per night

Guest favorite

Townhouse in Key West

4.91 out of 5 average rating, 267 reviews

Sparkling clean. Newly Updated Family Friendly

Great family home in the gated community of Coral Hammock, located just 10 minutes from the center of Key West. It boasts a beautiful salt water pool just steps away from the property. Perfect for families or groups of mature adults.

Oct 9 – 16

G$144,043 GYD per night