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.

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Guest favorite
A modern living area features a spacious layout with a comfortable seating arrangement and a large flat-screen TV mounted on the light green wall. Natural light floods in through expansive glass doors, revealing views of the outdoors. A stylish kitchen island with sleek countertops complements the space.
Condo in Key West
4.95 out of 5 average rating, 185 reviews

Fully renovated 2/2 bath condo w/ shared pool!

**Brand New Listing** Welcome to Captains Choice - The NICEST Unit at Sunrise Suites Key West, unit 302. Tropical winds, sunset views and Key West charm await when you book your stay in this gorgeous completely renovated two bedroom, two bathroom condo "Captain's Choice". Highlights include: Smart TVs in each room Keurig New stainless Kitchen/appliances In-unit, full size washer/dryer Located near restaurants, a convenience store, & Smathers Beach End unit One parking space, free of charge

Guest favorite
Aerial view showcasing a waterfront property bordered by vibrant green mangroves. The calm turquoise water reflects the blue sky dotted with white clouds. A marina with docked boats is visible nearby, creating a serene coastal landscape.
Condo in Key West
4.98 out of 5 average rating, 116 reviews

Gorgeous Ocean View in Paradise, Close to Key West

This is paradise! Wake up to a gentle breeze and birds singing just outside your balcony. Watch the sunrise over the ocean and mangroves from your private balcony. Enjoy your privacy as you start your day, then venture out to explore all that Key West has to offer: water sports, quaint shops, delicious food, history all around you, and so much more! On property features: Pool, Hot Tub, Yellowfin Bar & Kitchen and Parking. Beach supplies included: Coolers, Snorkel Gear and Beach Towels.

Top guest favorite
A spacious sleeping area features a king bed dressed in soft linens and adorned with decorative pillows. Natural light enters through sliding glass doors that open to views of the marina. Warm wood flooring complements the modern design.
Houseboat in Stock Island
4.96 out of 5 average rating, 47 reviews

The Writer's Block- Key West

Discover tranquility aboard this unique floating haven. It's a sleek modern retreat for those who crave space to read, write or find inspiration far from the stresses of the modern world --yet it's steps away from upscale restaurants, two fabulous pools, a gym and so much more. From a king bed to a full-sized shower and kitchenette, you'll enjoy the comforts of home while living directly on the water. Features a large private deck with panoramic views of the marina and its glorious sunsets.

Guest favorite
A wooden sign with the name 'Center Court' is prominently displayed, surrounded by lush tropical foliage. The sign features a decorative design and is mounted on a white post, indicating the location of the historic inn and cottages.
Home in Key West
4.91 out of 5 average rating, 233 reviews

McCartney's Manor - Deluxe K Suite W/Pvt. Spa!

Beautifully decorated, step inside with cool pastel colors. The amenities include a blue tooth speaker, Alexa Echo, and a full kitchen with dishwasher. End your day by relaxing in front of the 65" Smart TV (bring your login information for Netflix/Amazon). The tumbled marble shower adds a luxurious touch to your stay. Located in a gated compound with 3 other units, you'll have privacy during your stay. The heated family pool is next door, while the adult heated pool is across the lane.

Guest favorite
A serene waterfront view captures a light-colored building with turquoise accents, surrounded by lush palm trees. The calm water reflects the structure and sky, creating a tranquil atmosphere. Soft clouds float above, enhancing the peaceful setting of the marina.
Boat in Key West
4.82 out of 5 average rating, 158 reviews

A Great Escape! Private 2 Bed Rm Beautiful Marina

Our Marina has a pool and a small private beach overlooking the beautiful Keys water! More affordable than most places in Key West while able to reconnect with nature at this private getaway on the Great Escape. As you approach the boat, you feel your dream vacation has come true . One of a lifetime. Staying on a beautiful sportfisher yacht, laying in the waters of the calm keys and in the most beautiful peaceful marina, will definitely set you free from all your worries and stress.

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, 272 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 spacious living area features a comfortable futon adorned with a decorative pillow. Large windows provide views of the tranquil water, allowing natural light to brighten the space. The walls are designed in a soft, neutral tone, enhancing the overall welcoming feel.
Houseboat in Key West
4.94 out of 5 average rating, 158 reviews

Amazing houseboat with 2nd floor observation deck

Escape to our one-of-a-kind houseboat “Wild One,” anchored minutes from Soencers boat yard Key West. Surrounded by turquoise waters, enjoy one complimentary round trip per day, with times arranged around our charters. Evening rides may be available on request, last ride 10 PM. Extra charge after 8 PM Special Promotion: End your day with a private Sunset Eco Trip (6–7 PM) as your nightly ride to the houseboat—watch the sky ignite before settling in for a peaceful night afloat.

Top guest favorite
A spacious bed is framed by elegant side tables, each topped with a softly glowing lamp. Above the headboard, three framed artworks create a balanced focal point. Decorative pillows add a touch of color, while a leafy plant provides a natural element to the serene space.
Apartment in Key West
4.95 out of 5 average rating, 459 reviews

Studio Blu -Hip Studio/Old Town

*Recent Update (2025): We’ve made a wonderful upgrade to the studio bathroom — it’s now fully enclosed with walls extending to the ceiling and a new exhaust fan for ventilation. Situated in the heart of the Cuban district, just steps from arguably the best café con leche in Key West, this bright and breezy studio apartment is minutes from everything on the island. No car needed — bikes and beach chairs are provided free of charge so you can explore at your own pace.

Top guest favorite
Apartment in Key West
4.98 out of 5 average rating, 538 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.

Guest favorite
A serene pool area features a clear blue water swimming pool surrounded by lounge chairs and umbrellas. A lush landscape of palm trees and green foliage complements the setting, with a charming cottage visible in the background.
Townhouse in Key West
4.91 out of 5 average rating, 198 reviews

Poolside Cottage #411

Welcome! This beautiful cottage is located in the Coconut Mallory Resort & Marina on the eastern end of Key West. This secluded, waterfront oasis includes outdoor pools, hot tub, on-site marina and boat dock. There's also a new bar & grill, Gumbo's, in the resort. When you want to get out and explore KW, you're only minutes from beaches, the Seaport and world famous Duval Street! Bikes, kayaks, paddle boards and golf carts can be rented locally

Guest favorite
A spacious living room is furnished with a soft blue sofa and matching armchair. Light wooden flooring complements the room's bright atmosphere, and a coffee table sits in the center. Large sliding glass doors lead to a patio area, allowing natural light to fill the space.
Condo in Key West
4.9 out of 5 average rating, 159 reviews

Tropical Escape at Sunrise

We thoroughly sanitize upon check-out. This luxurious condo features a wonderful tropical interior design. It includes 2 spacious BR's: king bed/ full bath, queen bed/ full bath). Our living room sofa bed accommodates 1 guest. A fully equipped kitchen. Patio overlooks pool. WiFi, basic cable, 3 TV's, A/C, washer-dryer, workout center, BBQ, tennis court, elevator, parking. Accommodates no more than 5 guests. Must be 25 and older.

Guest favorite
Condo in Key West
4.92 out of 5 average rating, 118 reviews

Vacation home Island Suite 16

The Island Suite is part of a historic Key West property built around 1889. Suite #16 is located on the first floor at the rear of the 411 William Street building. The Island Suite has one of the premiere locations in Old Town, Key West with lively Duval Street just 3 blocks away and the neighborhood boasting some of the finest older homes in Key West.

Popular amenities for Stock Island family-friendly rentals

When is the best time to visit Stock Island?

MonthJanFebMarAprMayJunJulAugSepOctNovDec
Avg. priceG$89,311 GYDG$94,121 GYDG$84,918 GYDG$80,526 GYDG$73,206 GYDG$69,022 GYDG$66,512 GYDG$64,421 GYDG$55,636 GYDG$67,977 GYDG$74,251 GYDG$81,154 GYD
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Quick stats about vacation rentals that are family-friendly in Stock Island

  • Total vacation rentals

    Explore 280 vacation rentals in Stock Island

  • Nightly prices starting at

    Stock Island vacation rentals start at G$25,099 GYD per night before taxes and fees

  • Verified guest reviews

    Over 10,420 verified reviews to help you choose

  • Pet-friendly vacation rentals

    Find 80 rentals that welcome pets

  • Vacation rentals with a pool

    260 properties feature pools

  • Rentals with dedicated workspaces

    150 properties have a dedicated workspace

  • Wi-Fi availability

    260 of Stock Island vacation rentals include wi-fi access

  • Popular amenities for guests

    Guests love Kitchen, Wifi, and Pool across Stock Island rentals

  • 4.8 Average rating

    Stock Island stays are highly rated by guests—averaging 4.8 out of 5!

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