Family-friendly holiday rentals in Stock Island

4.93 out of 5 average rating, 27 reviews

Waterfront Boat Stay + Resort Amenities

A Whim isn’t just a place to sleep—it’s permission to unplug and let vacation unfold naturally. Docked at the exclusive Perry Hotel & Marina, this 40-foot, 2-bedroom luxury yacht is tucked away from the crowds, while remaining just minutes from downtown Key West. Featuring inviting indoor and outdoor spaces for living, dining, and relaxing, it offers the perfect balance of comfort and adventure. Guests enjoy hotel amenities, including two pools, a gym, and three waterfront bars and restaurants.

FamilyKitchenComfort

5 out of 5 average rating, 12 reviews

3BR In Resort Village, Pools, Free Kayak & Shuttle

Experience the ultimate KEY WEST VIBE aboard our 3BR/2BA sailboat Located at the luxury Perry Hotel, you’ll enjoy ice-cold AC, palm trees, and salty air. Free Perks: Kayak, pools, parking, and free shuttle to Old Town! Full Resort Access: 2 sparkling pools & hammock park, 2 restaurants, ice cream shop, private bathhouse & Views of million-dollar yachts Live the island life w full access to all resort amenities. Your tropical escape awaits! This memorable place is anything but ordinary.

FamilyBeachSleep quality

A motorboat is anchored on calm waters, featuring a spacious front deck. Two individuals are seated comfortably, enjoying the view. The boat's sleek design is complemented by a canopy overhead and small steps leading into the water, creating a relaxed atmosphere.

4.9 out of 5 average rating, 240 reviews

Stay on Roxie - free transport & snacks, BYOB.

Read our reviews and relax with last minute weather cancellation! 🌞 Shower, toilet and power to recharge phones, full cellular. Enjoy a peaceful night or two on the water! Free parking and one free round trip transport to/from Roxie per night stay! Roxie is anchored in ~3ft lagoon. We live on a boat a half-mile away if you need anything at all! Roxie has a Keurig, coffee pods, bread, peanut butter-jelly, and bottled waters. No cooking but you may bring to-go food, beer/booze/wine. 🛥️🌴🎣

FamilyKitchenComfort

4.87 out of 5 average rating, 212 reviews

A crystal-clear saltwater pool reflects the sunlight, surrounded by lush tropical landscaping. Several lounge chairs are positioned along the pool deck, while vibrant palm trees and greenery create a serene atmosphere in the backdrop.

Townhouse in Key West

*Sparkling new kitchen* 3 bedroom/3 bath home.

Coral Hammock was built in 2004. This home is a spacious 3 bedroom, 3 bath home in a beautifully landscaped gated community. It features 1 king size beds and two queen beds. The kitchen is fully equipped with modern appliances, dishes and cooking utensils. There is a new Whirlpool Duet washer/dryer installed. The salt water pool is perfect for lazing away your days. There is on street parking for two cars. The center of town is ten minutes away. An entire home for the price of one hotel room.

Indoor spacesKitchenAmenities

4.84 out of 5 average rating, 172 reviews

A shared pool area is surrounded by lush tropical landscaping, featuring palm trees and greenery. Sun loungers and umbrellas are arranged around the pool, offering ample space for relaxation. The water reflects the clear blue sky, creating a serene and inviting scene.

Townhouse in Key West

Charming Key West Vacation Rental 3bedrm/3bath

Beautiful gated home located in Coral Hammock just minutes away from Key West. It's a spacious 3 bedroom, 3 bath home with a full kitchen, living room, indoor and outdoor dining. With access to shared pool, club house and gym. Everything you need to enjoy vacation. We have also updated the unit with new flooring throughout! Beach Gear is also available Beach towels, beach chairs, beach toys, floats and cooler. Baby / Toddler. Portable Crib, high chair & more. Items available upon request

KitchenFamilyQuiet

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.

4.99 out of 5 average rating, 135 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.

Indoor spacesFamilyLocation

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.

4.83 out of 5 average rating, 177 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.

Indoor spacesKitchenAmenities

4.83 out of 5 average rating, 23 reviews

43' Classic Yacht Views, Pools, Duval Shuttle

Create unforgettable Key West memories while staying on our long time charming liveaboard 43' Trawler. This 2 bedroom 1.5 Bath mini yacht will be the perfect home base for your adventures around town or to just sit and enjoy the incredible views and nature. Being at the award winning Perry Marina gives you all the amenities of a 5 star resort. 2 Pools, 3 Restaurants on site, free shuttle to town, hotel gym, laundry and all the charter and adventure options you could ever ask for.

Indoor spacesKitchenQuiet

Cottage in Little Torch Key

A waterfront property is surrounded by lush palm trees, with a gravel area leading to a private dock. The home is painted in soft blue tones, reflecting a comfortable coastal vibe. The expansive water views offer shimmering reflections under the clear sky.

4.88 out of 5 average rating, 182 reviews

Waterfront Cozy Cottage with Boat Ramp & Dock!

Welcome to Paradise! Stay in the amazing Keys and beautiful waterfront home with 250 foot dock, ramp, and basin for your boat. It's a must-see rustic outdoor environment and fishery experience, very typical in the Keys! The property lot is almost an acre with a work section and still very spacious. Stunning panoramic water views, sunrise and sunset. Steps away from ocean water. Bring or rent fishing and snorkel gear nearby to fish right off the dock and enjoy the underwater scenery!

Indoor spacesKitchenLong stay

4.82 out of 5 average rating, 108 reviews

A heated pool is surrounded by a spacious deck, featuring lounge chairs and a dining table with blue chairs. Beyond the pool, a pathway leads to lush greenery and the ocean view under a partly cloudy sky.

Home in Cudjoe Key

Palm Breezes! Room for Everyone on the Ocean.

This 5 bedroom 3 bath house with pool on Ocean front property on Highway 1.. This lovely home has its own huge pool area with full lounge chairs all the way around pool area, the pool is heated. Grill, Jacuzzi. Full WiFi. TVs in every bedroom! Travel down our private dock way to the beautiful Cudjoe Bay, hop one of the many kayaks and take a healthy paddle with your friends/family or just enjoy the breathtaking ocean view while you sit on the porch.

Indoor spacesFamilyBeach

4.92 out of 5 average rating, 222 reviews

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

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

Indoor spacesKitchenSleep quality

4.93 out of 5 average rating, 230 reviews

The houseboat is anchored in the Cow Key Channel, featuring a sunlit exterior with a white finish. A deck extends from the entrance, complemented by a hammock and kayaks nearby. Clear blue skies and calm waters create a peaceful setting.

Houseboat in Key West

Beautiful Houseboat in Key West

Enjoy a unique and peaceful stay on our cozy houseboat in Key West. Perfect for couples or small families who want a relaxing water experience close to town. Comfortable sleeping area, deck space, and beautiful sunset views. Check-in is by appointment with personal captain meet-and-greet and boat transfer from the marina. A memorable island stay surrounded by nature and ocean air.

Indoor spacesFamilyComfort

Popular amenities for Stock Island family-friendly rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Family-friendly home rentals with a hot tub

4.8 out of 5 average rating, 101 reviews

Pool Access + Local Art • Walk to Southernmost

Indoor spacesKitchenAccess

The expansive outdoor pool is framed by palm trees and surrounded by lounge chairs with blue umbrellas. The area is well-lit and features a shaded pavilion. The surrounding building showcases tropical landscaping, providing a relaxing atmosphere for guests.

4.91 out of 5 average rating, 165 reviews

Key West Beachside 1400sf, 2 Bedroom Condo

KitchenFamilyBeach

A bright living area features light-colored furniture, including a comfortable sofa and armchair. A wooden coffee table is centrally placed. Art displays adorn the walls, enhancing the inviting ambiance. Nearby seating accommodates dining for four, with large windows allowing natural light to flow in.

4.88 out of 5 average rating, 106 reviews

Castaway Cove: Pet-friendly 2/2 condo near beach!

KitchenFamilyHospitality

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.

4.9 out of 5 average rating, 177 reviews

Tropical Escape at Sunrise

Indoor spacesFamilyQuiet

An Olympic size pool is highlighted in the image, surrounded by palm trees and lounge chairs. The building in the background offers several balconies, and a well-maintained garden area is visible, enhancing the outdoor setting next to the beach.

4.78 out of 5 average rating, 314 reviews

Affordable Beachfront Luxury Condo Sleeps 6

FamilyKitchenCheck-in

A charming entrance is framed by lush tropical plants and palm trees. The light green door complements the inviting beige exterior of the home. A cozy seating area is situated on the porch, and brick pathways lead through a landscaped yard filled with vibrant foliage.

4.94 out of 5 average rating, 107 reviews

Tropical Heron Hideaway w/ Hot Tub + Pool

Indoor spacesKitchenQuiet

4.97 out of 5 average rating, 309 reviews

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

Indoor spacesKitchenQuiet

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.

4.95 out of 5 average rating, 200 reviews

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

Indoor spacesKitchenLocation

Family- and pet-friendly home rentals

A well-maintained community pool is surrounded by lush tropical landscaping, featuring lounge chairs with blue umbrellas. The clear water reflects the bright blue sky and palm trees, creating a relaxing atmosphere for guests to enjoy.

4.88 out of 5 average rating, 93 reviews

Key West Paradise

FamilyIndoor spacesAccess

A spacious outdoor patio is viewed, featuring a dark wooden table and black wicker chairs. A decorative rope centerpiece is placed on the table. The horizon displays a vivid sunset with shades of orange, pink, and purple, casting a serene reflection over the calm water.

4.97 out of 5 average rating, 98 reviews

Oceanfront 3 bed condo Ocean Edge w/ optional slip

FamilyKitchenTV

Tiny home in Big Pine Key

A coastal scene showcases palm trees swaying gently by the water. Thatched roofs provide shaded seating areas along the shoreline. Sailboats are visible on the horizon, amidst clear turquoise waters under a bright blue sky, with a few fluffy clouds drifting by.

4.87 out of 5 average rating, 118 reviews

Cottage 30 min from Key West, free parking, pool

FamilyKitchenHospitality

4.97 out of 5 average rating, 31 reviews

An aerial view showcases the resort's central pool surrounded by palm trees and landscaped gardens. The inviting pool area is complemented by a spacious pavilion with a metal roof, providing a gathering space. The background features the resort's accommodations and the lush natural environment.

Condo in Summerland Key

Family Suite at Sugarloaf Key Hotel (Pet Friendly)

KitchenFamilyLayout

4.88 out of 5 average rating, 139 reviews

A cozy living space features a navy blue sofa adorned with nautical-themed throw pillows. A dining area with a glass table and chairs is visible in the background, alongside a decorative display of framed art and a potted plant. Natural light filters through the windows.

Houseboat in Marathon

Houseboat Getaway In Marathon

Indoor spacesFamilyView

A bright and airy living space features a large sectional sofa, a dining area with a light-colored table and chairs, and large glass doors leading to a balcony with water views. Light wood paneling and artwork enhance the overall ambiance.

4.88 out of 5 average rating, 266 reviews

Waterfront Dock Pool Condo Near Duval St Pet OK

Indoor spacesKitchenHospitality

4.87 out of 5 average rating, 60 reviews

Houseboat in Key West

Indoor spacesKitchenPets

A well-maintained two-story house features light-colored siding and contrasting blue shutters. A spacious, welcoming front porch is framed by tropical plants and neatly arranged landscaping. Steps lead up to the front door, providing easy access to the entrance.

5 out of 5 average rating, 33 reviews

Casa Calypso 3bed3bath sleeps 8 beautiful decorate

FamilyIndoor spacesValue

Family-friendly home rentals with a pool

4.85 out of 5 average rating, 26 reviews

Sentient Waters: 63’ Boat, Free Snorkel Gear, etc.

Indoor spacesFamilyCleanliness

A lush garden expanse is depicted, featuring vibrant greenery and colorful flowers. Palm trees sway in the gentle breeze, while the ocean is visible in the background. A pool is nestled within the landscaped area, complemented by a shady outdoor dining space under a canopy.

5 out of 5 average rating, 3 reviews

Best Resort in Key West, 2BD/2BA

FamilyLocationPool

5 out of 5 average rating, 15 reviews

Key West Beach House

Indoor spacesFamilyValue

A modern living area is presented with a comfortable grey sofa and two patterned chairs facing a large sliding door. Natural light fills the space, illuminating a textured wood coffee table and a side table with a lamp. A mounted television displays vibrant sunset imagery.

4.99 out of 5 average rating, 77 reviews

Newly Renovated 2/2 Bath Condo, with shared pool

Indoor spacesFamilyLocation

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.

4.99 out of 5 average rating, 80 reviews

EYW Getaway

Indoor spacesFamilyQuiet

A spacious swimming pool is surrounded by lush tropical greenery and lined with lounge chairs. Tiki-style huts provide shaded areas for relaxation, while the pool's clear blue water reflects the vibrant sky, creating a serene and inviting environment.

5 out of 5 average rating, 40 reviews

Funky Chicken Cottage with Shared Pool in Paradise

FamilyKitchenBathroom

5 out of 5 average rating, 11 reviews

Oceanview condo w/pool, jacuzzi

FamilyKitchenBeach

The sailing catamaran Purpus is shown gliding over the water, featuring a sleek white hull and a large deck. A spacious area is visible at the bow with crew members actively adjusting the sail. The overall design emphasizes both function and elegance.