Family-friendly holiday 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

Superhost
Apartment in Key West
4.61 out of 5 average rating, 84 reviews

Beautifully Renovated Summer of 2020 Come and enjo

RandyRating, 5 stars6 days ago
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!!
Superhost
Home in Cudjoe Key
4.63 out of 5 average rating, 166 reviews

Ocean Front Home in Great Location

HaroldRating, 5 stars2 weeks ago
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.
Top guest favourite
Apartment in Key West
5 out of 5 average rating, 33 reviews

EYW Getaway

JaneRating, 5 stars1 week ago
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.
Superhost
Home in Cudjoe Key
4.8 out of 5 average rating, 92 reviews

Palm Breezes! Room for Everyone on the Ocean.

GerritRating, 5 stars2 months ago
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!!
Superhost
Apartment in Key West
4.84 out of 5 average rating, 38 reviews

Henry's Piece of Paradise On The Ocean In Key West

DonaldRating, 5 stars2 months ago
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!
Superhost
Apartment in Key West
4.62 out of 5 average rating, 240 reviews

Sunrise Suites Resort Key West, FL U #111 2bdr2bth

ElmerRating, 5 stars4 months ago
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.
Guest favourite
Home in Key West
4.82 out of 5 average rating, 94 reviews

Historic Key West - Conch House - Sleeps 5

Trevor And LoriRating, 5 stars3 weeks ago
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!
Superhost
Home in Key West
4.83 out of 5 average rating, 29 reviews

Casablanca Too ~Chicly updated home with hot tub

AdamRating, 5 stars2 months ago
Great host and loved the place. Was perfect for our trip.

Family- and pet-friendly home rentals

Cabin in Marathon
4.53 out of 5 average rating, 205 reviews

Tropical Cottages - Cottage # 7

RobertRating, 5 stars1 month ago
Very cute and unique place. Location excellent to everything you need in less than 2mi
Superhost
Townhouse in Marathon
4.82 out of 5 average rating, 17 reviews

Waterfront luxury Villa (34) with sunset views and boat slip

AngelaRating, 5 stars30 months ago
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.
Home in Marathon
4.82 out of 5 average rating, 34 reviews

Waterfront, dock, easy ocean access, heated pool!

MelissaRating, 5 stars14 months ago
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:))
Superhost
Home in Marathon
4.46 out of 5 average rating, 13 reviews

Kon Tiki ~ Waterfront Pool Home, 30' Dock

DarleneRating, 5 stars17 months ago
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.
Guest favourite
Villa in Marathon
4.88 out of 5 average rating, 58 reviews

New Paradise On Sombrero Beach

JenniRating, 5 stars1 month ago
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!
Townhouse in Little Torch Key
4.77 out of 5 average rating, 91 reviews

Waterfront 2BD / 2.5BTH Luxury Townhome

AlexRating, 5 stars1 month ago
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!
Home in Marathon
4.96 out of 5 average rating, 163 reviews

Vida De Aqua - Water Life!

BrianRating, 5 starstoday
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!
Superhost
Campsite in Big Pine Key
4.73 out of 5 average rating, 120 reviews

Bring Your Own RV! Our Lot Your RV B6 No Tents

CarolynRating, 5 stars2 months ago
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

Home in Cudjoe Key
4.45 out of 5 average rating, 40 reviews

Fabulous Florida Keys!

TinaRating, 5 stars24 months ago
It was beautiful and very peaceful. Everyone was so nice and very helpful. The house was beautiful and so clean.
Superhost
Townhouse in Marathon
4.8 out of 5 average rating, 51 reviews

Beautiful Coral Lagoon #12 in #1 Resort - Marathon

KaceyRating, 5 stars3 months ago
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.
Home in Marathon
4.89 out of 5 average rating, 19 reviews

NEW LUXURY 4/3 SINGLE FAMILYw/HEATED P00L,BOATDOCK

BradleyRating, 5 stars10 months ago
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!
Guest house in Big Pine Key
4.48 out of 5 average rating, 54 reviews

RV Lot Land Only W/ Hook-Ups, Pool.

ShawnRating, 5 stars34 months ago
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!!
Home in Marathon
4.9 out of 5 average rating, 20 reviews

Villa Casa Cayo

AmyRating, 5 stars5 months ago
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.
Superhost
Apartment in Key West
5 out of 5 average rating, 22 reviews

Saltwater Harmony @ The Annex - Charming Condo

KrisRating, 5 stars12 months ago
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
Apartment in Key Colony Beach

3 Bedrm Condo on Ocean (7 day min.)

LourdesRating, 5 stars23 months ago
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.
Superhost
Townhouse in Key West
4.77 out of 5 average rating, 181 reviews

Nassau Suite just steps to Duval Tropical oasis q

BenRating, 5 stars3 weeks ago
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

Destinations to explore

  1. Airbnb
  2. United States
  3. Florida
  4. Monroe County
  5. Key West
  6. Key Haven
  7. Family-friendly rentals