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

King MSTR, SS Quartz Kitchen, Bikes Kayaks, VIEWS!
Updated waterfront 2BR/2BA with King Master, 2nd Queen and pullout couch. 35' seawall—bring your boat! Enjoy a fully stocked quartz kitchen with stainless appliances. Located in Venture Out, a quiet, family‑friendly gated resort with fishing, lobstering, pools, hot tub, pickleball, tennis, basketball, rec center, bikes, kayaks, and SUPs. Between Key West (20 mi) and Marathon. Free WiFi; Roku TVs in both bedrooms and living room. Kayaks, SUPs and storage area with extra fridge and bait freezer.

Romantic Retreat - 2 person K Suite, Pvt deck/Spa!
Romantic Retreat is an Historic, free standing cottage which, in the 1800's, was the cistern for the Cigar Maker cottages here. It is decorated in a light Caribbean motif, efficiency kitchen (frig, microwave, hot plate) and a very airy bathroom with tub/shower. King memory foam bed and sleeps 2 persons only. 32” Smart TV (bring your Netflix, Amazon UN/PW's). Bose Bluetooth speaker, Amazon Alexa provided. A private adjacent deck with a 2 person Solana spa/seating. Also handicapped accessible.

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. 🛥️🌴🎣

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.

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.

Luxury 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 ft 2-bed luxury boat with island bright touches is tucked away from the crowds in a resort style marina while being just minutes from downtown Key West. Featuring indoor and outdoor spaces for living, dining, and relaxing, as well as hotel amenities such as a pool, 3 bars and restaurants, and a gym. Vacation differently on A Whim.

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.

Poolside Cottage #412
Welcome! This beautiful cottage is located in the Coconut Mallory Resort & Marina on the eastern end of KW. This secluded, waterfront oasis includes outdoor pools, hot tub, on-site marina and 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, golf carts, kayaks, stand-up paddleboards and other watercraft can all be rented locally!

Waterfront Haven House with Boat Basin & Ramp!
Welcome to Paradise! Stay in the amazing Keys and beautiful waterfront home with boat basin and ramp for your boat. The property lot is almost an acre with another rental home and still very spacious (search for Anchor House to reserve both homes if available). 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 point and enjoy the underwater scenery!

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.

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.

Affordable Beachfront Luxury Condo Sleeps 6
My place sits on Smather's beach! Close to downtown and the airport. You’ll love the condo because of the location, the large indoor space, it's quiet, the pool, and has all the comforts of home. My condo is good for couples, solo adventurers, business travelers, families (with kids), and big groups. It’s spacious - and very clean!
Popular amenities for Key Haven family-friendly rentals
Family-friendly home rentals with a hot tub

Tropical Escape at Sunrise

EYW Getaway

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

Palm Breezes! Room for Everyone on the Ocean.

Waterfront Sanctuary in the Keys!

Oceanview condo w/pool, jacuzzi

KW Luxury 2/2 Beachfront resort Tropical Oasis

Moonlight Paradise Upgraded Family oasis Tropical
Family- and pet-friendly home rentals

Key West Paradise

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

Kelly’s Kabin - Private FL Keys Cottage

Cottage 30 min from Key West, free parking, pool

Oceanfront 3 bed condo Ocean Edge w/ optional slip

Palm - Beach Houses Key West

Aquahouse Paradise easy access to the ocean

Classic 30’ Sailboat
Family-friendly home rentals with a pool

Waterfront, Dock, Pool, Pickleball, near Key West!

Condo de Paradise/Salt Water Pool/Boat Dock

Sunset Harbor 2 bed Ocean views!

TortugasHarbor Light Suite

Boat life with all the amenities

Funky Chicken Cottage with Shared Pool in Paradise

Waterfront Condo FREE Slip & Pool 2B2B in Key West

Rise And Shine On The Water
When is the best time to visit Key Haven?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $1,105 AUD | $1,323 AUD | $1,798 AUD | $1,447 AUD | $1,369 AUD | $1,172 AUD | $1,415 AUD | $1,329 AUD | $1,075 AUD | $1,068 AUD | $1,458 AUD | $1,667 AUD |
| Avg. temp | 21°C | 22°C | 24°C | 25°C | 27°C | 29°C | 30°C | 30°C | 29°C | 27°C | 25°C | 23°C |
Quick stats about holiday rentals that are family-friendly in Key Haven

Total holiday rentals
Explore 70 holiday rentals in Key Haven

Nightly prices starting at
Key Haven holiday rentals start at $128 AUD per night before taxes and fees

Verified guest reviews
Over 1,180 verified reviews to help you choose

Pet-friendly accommodation
Find 40 rentals that welcome pets

Holiday rentals with a pool
60 properties feature pools

Rentals with dedicated workspaces
50 properties have a dedicated workspace

Wi-Fi availability
70 of Key Haven holiday rentals include Wi-Fi access

Popular amenities for guests
Guests love Kitchen, Wifi and Pool across Key Haven rentals

4.9 Average rating
Key Haven stays are highly rated by guests—averaging 4.9 out of 5!
Destinations to explore
- Rentals with a patio Key Haven
- Pet-friendly rentals Key Haven
- Rentals with a washing machine and dryer Key Haven
- Waterfront rentals Key Haven
- Luxury rentals Key Haven
- House rentals Key Haven
- Rentals with pools Key Haven
- Rentals with outdoor seating Key Haven
- Fitness-friendly rentals Key Haven
- Family-friendly rentals Key West
- Family-friendly rentals Monroe County
- Family-friendly rentals Florida
- Family-friendly rentals United States
- Sombrero Beach
- Smathers Beach
- Calusa Beach & Loggerhead Beach
- Long Beach
- Bahia Honda State Park
- Fort Zachary Taylor Historic State Park
- Seven Mile Bridge
- Ernest Hemingway Home & Museum
- Sunset Park
- Key West Lighthouse Museum
- Florida Keys Aquarium Encounters
- Key West Butterfly & Nature Conservatory
- The Turtle Hospital
- Boyd's Key West Campground
- Southernmost Point




