
Family-friendly vacation rentals in Sunset Key
Find and book unique family-friendly homes on Airbnb
Top-rated family-friendly rentals in Sunset Key
Guests agree: these family-friendly homes are highly rated for location, cleanliness, and more.

ATLANTIS...Ocean Front Cottage Retreat!
ATLANTIS~An ocean front cottage retreat! Completely remodeled, direct ocean-front cottage offers everything you'll need for the perfect getaway. Boat dock (25ft), HD TVs, washer & dryer, S/S appliances & gas cooking! Complimentary kayaks & bikes plus access to all the Venture Out Residential Condominium Community amenities: heated pool, Jacuzzi, kiddie pool, tennis, basketball & bocce courts, ocean bay swimming area, marina w/fuel, boat ramps & wash station, and a convenience market on-site!
Indoor spacesKitchenLocation

Duval Vibes • Pool • 10 Guests
Located only 30 seconds from Duval Street, this house will be your Key West headquarters for bachelor parties, family reunions, or any celebration that bring you to town. This 3 bedroom/ 2.5 bathroom home has a full kitchen, spacious outdoor living space, outdoor shower, private second story sundeck, and a pool. Your group of up to 10 will love being steps away from all KW has to offer- be Hemingway's neighbor! Add this listing to your wishlist by clicking the ♥ in the upper right hand corner.
KitchenFamilyPool

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. 🛥️🌴🎣
KitchenFamilyHeating

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, renovated kitchen with granite counter tops, 2 burner stove, under counter fridge/freezer, dishwasher, microwave, air fryer/oven tumbled marble 2 person shower, private front deck with seating for 4, 2 person Solana spa. Perfect for a couple or a family with children. Freshly painted a Caribbean blue with plantation shutters.
Indoor spacesKitchenGetting around

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.
KitchenIndoor spacesValue

Cuban Paradise @ Cuban Club
Built in 1917 as a “club” for Cuban cigar makers and their families as their home-away-from-home, this building soon became the center of social and community life for the Cuban population in Key West. After the original Cuban Club burned down in 1983, it was restored and converted to luxurious and spacious suites. Escape the stress and cares of your daily life with a vacation to the wonderful Cuban Paradise! This roomy two-bedroom condo has a private balcony to enjoy all the hustle and
Hospitality

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 spacesFamilyView

Cudjoe Key Home with a View
We are so excited to share our little piece of paradise with you! Our unit is located a short walk away from all the amenities the Venture Out community has to offer such as a pool, hot tub, lagoon, bocce ball, tennis courts, playground and boat marina. On the property we have a 2-person hybrid kayak for your enjoyment. We also provide table games (we love a game night) as well as the equipment to play bocce ball and darts which can be played in the recreation center.
KitchenIndoor spacesBathroom

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 spacesFamilySleep quality

Tropical Heron Hideaway w/ Hot Tub + Pool
Welcome to our charming 1932 Key West retreat in the peaceful Meadows neighborhood. This unique getaway features a private porch, a private hot tub, access to a shared pool and BBQ grill, and all the comforts of home. Blending historic island charm with modern amenities, it’s just minutes from Duval Street, the Historic Seaport, beaches, restaurants, and local attractions—the perfect place to relax and experience authentic Key West.
Indoor spacesFamilyAir conditioning

*Emerald Seas*-Florida Keys Ocean Front Paradise!
Welcome to our Florida Keys Ocean Paradise, Emerald Seas! Truly a special place to get away and relax. Enjoy the crystal-clear waters and amazing views. Bring or rent a boat, look for sea turtles, manatees, dolphins, lobster & tropical fish right from your patio or dock. Take in a glorious sunrise or moonlit night over the water. The amazing, 180 degree panoramic ocean views will take your breath away every moment you are there.
KitchenIndoor spacesHospitality

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.
KitchenIndoor spacesPool
Popular amenities for Sunset Key family-friendly rentals
Family-friendly home rentals with a hot tub

KW Luxury 2/2 Beachfront resort Tropical Oasis
Indoor spacesKitchenBiking

King MSTR, SS Quartz Kitchen, Bikes Kayaks, VIEWS!
Indoor spacesFamilyPool

Affordable Beachfront Luxury Condo Sleeps 6
Indoor spacesKitchenAmenities

Anchor Drop modern elegance upgrades throughout vi
FamilyIndoor spacesHot tub

Penthouse in Paradise
FamilyIndoor spacesHospitality

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

Key Wes't Best- Upgraded condo 5 mins to Smathers
Indoor spacesFamilyQuiet

Key West Beachside 1400sf, 2 Bedroom Condo
Indoor spacesFamilyHot tub
Family- and pet-friendly home rentals

Waterfront Condo Dock Pool Near Duval St
Indoor spacesFamilyAmenities

Cottage 30 min from Key West, free parking, pool
FamilyIndoor spacesWalkability

Paradise found
FamilyIndoor spacesValue

The Dancing Rooster - 1 Block to Duval!
FamilyIndoor spacesLayout

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

Key West Outpost: eco-vacation
FamilyKitchenCheckout

Starlight Serenity - Hideaway with Stunning Views
FamilyKitchenGetting around

KW CanalFront 3BR: Htd Pool, Boat Tie-Up, Pet OK
Indoor spacesFamilyLayout
Family-friendly home rentals with a pool

Historic Cigar House. 3rd floor Suite W/Kitchen
FamilyIndoor spacesCondition

A Great Escape! Private 2 Bed Rm Beautiful Marina
FamilyIndoor spacesLaundry

Waterfront Condo FREE Slip & Pool 2B2B in Key West
Indoor spacesKitchenWifi

Waterfront Boat Stay + Resort Amenities
FamilyKitchenGetting around

Wake Up On The Water | Luxury Marina | Key West
FamilyKitchenBathroom

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

White House - Receive $400 towards a Boat Rental!
Indoor spacesKitchenComfort

Sentient Waters: 63’ Boat, Free Snorkel Gear, etc.
FamilyIndoor spacesPool
Destinations to explore
- Miami Vacation rentals
- Four Corners Vacation rentals
- Miami Beach Vacation rentals
- Orlando Vacation rentals
- Fort Lauderdale Vacation rentals
- Tampa Vacation rentals
- Hollywood Vacation rentals
- Kissimmee Vacation rentals
- Key West Vacation rentals
- Cape Coral Vacation rentals
- Nassau Vacation rentals
- St. Petersburg Vacation rentals
- House rentals Sunset Key
- Rentals with a hot tub Sunset Key
- Waterfront rentals Sunset Key
- Cottage rentals Sunset Key
- Beachfront rentals Sunset Key
- Rentals with pools Sunset Key
- Pet-friendly rentals Sunset Key
- Rentals with beach access Sunset Key
- Condo rentals Sunset Key
- Family-friendly rentals Key West
- Family-friendly rentals Monroe County
- Family-friendly rentals Florida
- Family-friendly rentals United States
- Sombrero Beach
- Smathers Beach
- Bahia Honda State Park
- Ernest Hemingway Home & Museum
- Seven Mile Bridge
- Fort Zachary Taylor Historic State Park
- Southernmost Point
- Key West Butterfly & Nature Conservatory
- Key West Lighthouse Museum
- Boca Grande Key
- Mel Fisher Maritime Museum
- Truman Little White House
- Key West Aquarium





