
Family-friendly holiday rentals in Key Haven, Key West
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Top-rated family-friendly rentals in Key Haven, Key West
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Popular amenities for Key Haven, Key West family-friendly rentals
Family-friendly home rentals with a hot tub

Beautifully Renovated Summer of 2020 Come and enjo
The place was very peaceful. The courtyard was like a bird sanctuary with doves singing in the morning. It was safe and secure and very lush landscaping!!

Ocean Front Home in Great Location
This booking was great for what we needed, thank you to the responsive hosts and pet friendly house that made our vacation that much better.

EYW Getaway
We were next to the airport but didn't hear the planes. It was far away from Key West tourist attractions and restaurants. It was nice to come back to our place for peace and quiet. It was nicely decorated and felt like a beach get-away.

Palm Breezes! Room for Everyone on the Ocean.
10 out of 10 stay. Beautiful, serene property where we often felt we had the mangrove and key to ourselves. Several days were spent on a recurring rotation of kayaking, pool, hot tub, repeat. Perfect distance from Key West for adventuring there, but plenty on Cudjoe Key and Big Pine if you don't want to venture to the hustle and bustle. Sincerely hope to return!!

Henry's Piece of Paradise On The Ocean In Key West
Our stay was great. We had detailed instructions, the unit itself was decorated nicely, and the amenities within the building were great (pool and spa). Also the private beach area and walkability to food, snacks, restaurants was great!

Sunrise Suites Resort Key West, FL U #111 2bdr2bth
Very nice place to stay without breaking the bank. Lyft and Uber are always available to get you to where you want to go or rent a golf cart. Very responsive host, we will definitely be back.

Historic Key West - Conch House - Sleeps 5
Booked this last minute & it was a breeze to do so due to Steve’s quick responses. We’ve stayed in at least a dozen different places in KW & this place was great! The location was ideal. So easy to walk to several restaurants that we love, plus super close to the Green Parrot which is typically our last stop of the night. Quick walk to a liquor store & convenient store as well. The place felt so private & quiet (the roosters are the roosters, it’s Key West!)! The pool was ideal for the warm weather. We would stay here again!

Casablanca Too ~Chicly updated home with hot tub
Great host and loved the place. Was perfect for our trip.
Family- and pet-friendly home rentals

Tropical Cottages - Cottage # 7
Very cute and unique place. Location excellent to everything you need in less than 2mi

Waterfront luxury Villa (34) with sunset views and boat slip
Great place and location. Close to lots of restaurants. Pool was really nice! Kitchen was fully stocked and nice that they provide paper towels/toilet paper/dishwasher detergent/etc. to get you started. Had a nice bottle of champagne waiting for us upon arrival as well.

Waterfront, dock, easy ocean access, heated pool!
This house was a perfect spot for my partner and I and Cooper our pup. swam in the pool, sat in jacuzzi, paddle boarded ,kayaked, road the bikes, ect. we brought our boat down but unfortunately had a few issues with it so wasn't able to go out fishing as much as we'd liked. but there was plenty to do at and around this beautiful place. would definitely come back in the future:))

Kon Tiki ~ Waterfront Pool Home, 30' Dock
Kon-Tiki is in an outstanding location, and offers so many outdoor activities! We launched the house kayaks in the canal from the house dock, and paddled through the canals of beautiful homes, boats, and mangroves to the ocean’s edge and back. We rode the bicycles provided, and walked to Sombrero beach. We relaxed in the pool, and on the dock. We rented a boat for three days, and docked it at the house. We went cruising, snorkeling, and fishing in it. The back yard is very private and beautiful, with palm trees and lush vegetation. The kitchen is beautiful, and well-stocked. We cooked several times. I liked the deep washer and dryer. The upstairs, king size bed was comfortable. There is a lot of closet space.

New Paradise On Sombrero Beach
The house was well equipped with all of the essentials. We had 8 adults and plenty of room. We did have to wash towels a few times, and buy more laundry soap, but the washer and dryer were conveniently located on the main level. The pool was smaller than what the pictures showed, but it perfectly suited our needs. All members of our party viewed the listing before we booked it and none of us realized it was a twin home. However, there is tons of privacy and the only times we noticed we had neighbors was when the shared dock was used. We had to buy a cooler (for poolside and the beach) and beach chairs. There were some pool floaters left behind, from previous guests that we used. The interior of the home is beautiful, with high ceilings and comfortable furniture. This is in a great location - close to grocery stores, restaurants and Sombrero beach! Monica was great to work with!

Waterfront 2BD / 2.5BTH Luxury Townhome
Wonderful place to stay and great location for multiple key adventures throughout your stay. My family and I enjoyed the stay. We will definitely stay with little torch cottages again!

Vida De Aqua - Water Life!
Pure paradise! This private corner-lot home on the water gave us everything we dreamed of for our Keys getaway. Our boys fished from dawn to dusk while we kicked back, relaxed, and enjoyed the incredible peace, quiet, and space—it truly felt like our home away from home. The location is unbeatable: a quiet, friendly neighborhood that’s close to everything but feels like a private retreat. Inside was spotless, comfortable, and thoughtfully equipped—perfect for cooking, bathing, sleeping, and recharging after long days outdoors. The window A/Cs in the bedrooms were loud but kept things ice cold, and the kitchen ants are just part of life in the Keys. The bait freezer in the garage was perfect for our week of fishing. We loved having use of the 1-car garage—super convenient for tossing in all our beach and fishing gear at the end of the day. There were plenty of towels, extra sheets, and everything we could possibly need in the kitchen and bathrooms. We can’t wait to come back! 5 stars!

Bring Your Own RV! Our Lot Your RV B6 No Tents
The RV lot was well landscaped making the space feel tropical. Access to bath and laundry facility were just a few steps from the lot.
Family-friendly home rentals with a pool

Fabulous Florida Keys!
It was beautiful and very peaceful. Everyone was so nice and very helpful. The house was beautiful and so clean.

Beautiful Coral Lagoon #12 in #1 Resort - Marathon
Our stay was great for a family of 5. Vaulted ceilings, CLEAN bathrooms, nice tile, fixtures, plush towels and bath rugs, lots of pool towels, large couch, huge dining table, immaculate stocked kitchen, ice and water dispensers in fridge, short walk to a heated pool, deep canal steps away (under construction) and next to a full service marina. Parking easy, check in seamless. Great for kids lots of space to spread out, multiple porches, quiet, central location. Brian was easy to work with. Could improve: Master bath barn door (not shown in listing) did not open/close easily. The toilet is awkwardly close to the bed (you can reach the bed from the toilet). Also, if you can get the barn door shut, the gaps btwn the door are so big it doesn’t offer any privacy. We used the other 2 toilets in the house instead of the one in the master. A regular door there would be a big improvement. Beds were average, sheets were low quality, window blinds, pots and pans have seen better days.

NEW LUXURY 4/3 SINGLE FAMILYw/HEATED P00L,BOATDOCK
It was an awesome place! Beautiful, clean, and cozy! You can pull your boat right up to the dock! easy access threw the canal to the ocean and a couple of restraunts! pools nice! plenty of room for a big family! All of your amenities are nearby! Grocery store, restraunts, bars if your into that, gift shops and more!

RV Lot Land Only W/ Hook-Ups, Pool.
The space was a bit small however, our RV is a 23' travel trailer and fit nicely. A very quiet RV Park with an outstanding pool! :) Big Pine Key is a nicely centered Key that is only about 30 min from Key west. This is NOt an RV Resort....so don't expect paved camping sites or fire pits to cook smores. This is a area where the lots are owned by private owners who live there or rent their spaces out. Looks like a rough neighborhood when you first pull in but the people there are very friendly! The Key Deer are everywhere so if you have a dog, please make sure they are on a leash. We loved our stay and Jodi was an awesome host!!

Villa Casa Cayo
This home was just what my family needed for our vacation! We all loved relaxing in the outdoor living room surrounded by greenery. We also enjoyed swimming in the pool and kayaking through the canals and Boot Key. We made most of our meals due to dietary restrictions, and the kitchen here was adequate. The location in Marathon is excellent! It was just a 5-minute walk to Sombrero Beach, so we never had to worry about parking. We could easily drive to all the activities we wanted to do in the area, too.

Saltwater Harmony @ The Annex - Charming Condo
Had an incredible stay at Sweet Harmony! Super nice place with a great pool and the location was perfect. Everything was provided and the process was Super smooth. I was contacted throughout the process about every detail and Christian sent messages daily to check in or if I needed anything! Highly recommended......Would definitely stay here again! Thank you

3 Bedrm Condo on Ocean (7 day min.)
Our stay was amazing. The staff that runs the condo very friendly always cleaning all the common areas. Peter kept the beach areas clean every morning. Very quiet we rented kayaks and paddle that out to the sandbar every day. It was beautiful.

Nassau Suite just steps to Duval Tropical oasis q
Convenient location to walk pretty much anywhere! Very neat and tidy house
Quick stats about holiday rentals that are family-friendly in Key Haven, Key West
Total rentals
80 properties
Nightly prices starting at
$116 SGD before taxes and fees
Total number of reviews
900 reviews
Pet-friendly rentals
40 properties allow pets
Rentals with a pool
70 properties have a pool
Rentals with dedicated workspaces
50 properties have a dedicated workspace
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