
Kid-friendly holiday rentals in Stock Island
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Top-rated family-friendly rentals in Stock Island
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Popular amenities for Stock Island family-friendly rentals
Kid-friendly house rentals

Key West Paradise
Tammy was wonderfur, loved how attentive. The house was beautiful and close to so many great restaurants and things to do. Next door was the marina rented the boat, had a great breakfast at the French bakery down the street we could walk too almost everything. Loved it!!

Waterfront Cozy Modern Retreat w/Deep Canal
Christy was the best host! She was always available for quick questions and gave us great information as well. Her home was gorgeous! Beautifully decorated, flooring was luxurious and the space was perfect for the 2 us and our boat. The back porch was comfortable and the gas grill was a work of art! The boat ramp was a 1 mile away, Publix and Winn Dixie right around the corner and many restaurants all around made the location perfect for us. We had such a great stay and would definitely stay here again!! Thank You Christy for sharing your beautiful home with us!

Cancellation Deal: 08/02 thru 08/09
The house was very clean and inviting upon arrival. Nice location short drive to great restaurants and local grocery stores also less than 5min walk to the beach. Mr Eddie responded in a timely manner when we had questions. All in all we had a great time and very much enjoyed our stay! Thanks Mr Eddie

Cudjoe Key Home with a View
Everything was great. We enjoyed the pool, pickleball, and the water. The house was perfect for the area. Definitely recommend!

106 Newly Renovated House with Oceanview and Pool
As always, Michael’s place was spotless, perfectly stocked and just as pictured. We come back here annually to fish at Sugarloaf Marina and are always satisfied. Michaels house is in the perfect location, with the best sunsets, an amazing dock and pool, and the house is always stocked and we're able to relax for another day of tarpon fishing.

Gorgeous Romantic Private Villa, Steps from Duval!
We had a fantastic stay at Villa Serendipity. Great location right off Duval Street within walking distance to everything. Private and secluded. The pool is small and shared with 12 units, but it was nice. The courtyard is welcoming and peaceful. Bed was very comfortable. Well appointed kitchen; having the ice machine was great! Hosts communicate well. Parking was tight but once we got a spot we didn’t move the car for the rest of the trip. Overall had a great time at this excellent spot in Key West!

Waterfront Home 37.5-ft dock, Cabana Club Included
We were very comfortable at the home during our week stay. Great place to stay if you need room to park a boat trailer. Quiet very nice safe neighborhood.

Kittyhouse on Catherine, Tropical Pool, Parking
We loved our stay! It rained most of the time, but Alan’s place made up for that with a lovely pool and gorgeous views of the tropical landscape from the patio. The spaces were comfortable and very clean and the washer/dryer access was a major plus for us. The location was excellent with walkable restaurants and short drives to all of the major things to do and see. Alan was an extremely courteous and responsive host. I would highly recommend his place to others!
Family-friendly apartment rentals

Key West - Sunrise ❀ The Green House
Great spot, super close to everything but never disturbed by late night noise. Balcony is awesome to have !

Mango Hideaway @ the Eyebrow House off Duval
Great place with awesome location. Unfortunately I broke my ankle 2 days before our trip so my husband had to carry me on his back up the stairs to get in. I would definitely stay again but without the broken ankle next time!🤣

Heron Hideaway
Great place to stay while in Key West far enough from Duval to be quiet yet close enough to walk to wherever you want to go. Very responsive host. The accommodations were just as pictured and described. I would recommend this place.

Studio Near Downtown - The Bartlum
Conveniently located spot that is walking distance to Duval and all the nearby restaurants and sights!

Duval Street Suites full kitchen, free parking, &
This is a nice place with parking included and a nice swimming pool. It is right at Duvall street and 20 minutes walk with toddler to the Mallory square and 15 mins walk to the Southern most point. Sunscreen and aloes and beach towel and a candy jar is provided at the general area which is a nice touch. There are 2 roosters and hens and baby chicks hanging around at the parking lot area is pretty cool . Overall is very nice and will go back for sure

Beachfront Condo w/ Ocean Views in Marathon
This was our first family trip to the Keys and this location in Marathon was ideal! The condo was welcoming, beautiful and spacious for our family of 3. The balcony was our favorite place, which overlooked the pool and the seashore. The beach was lovely for shorter walks and just "being" with the ocean. Fun seashells & hermit crabs at low tide! Lots to do in the area -- definitely hoping to return next year. Mike was fantastic host & super helpful with questions.

Duval St Apartment w/ Balcony w/parking Adult Only
Amazing place to stay. We stayed for 2 nights and loved how walkable all the main places we wanted to go to were. The accommodation was amazing and loved the facilities, especially the pool!

#201 Key West Suites
This was our second stay here and it was great! They didnt have someone checking out the morning of our check in so they let us check in early whenever we arrived. It’s easy to get into the unit and the location is very walkable to bars, restaurants and shopping. I would highly recommend staying here if you are looking for a great location!
Family-friendly apartment rentals

La Dolce Vita, Old Town Steps to Duval! 3 blks bch
Right next to Duval Street, easily walkable to major attractions, restaurants, bars.. Host was super responsive, friendly, and really worked with us on anything we needed.. Great place!

Oceanfront Sunrise Condo Private Beach Heated Pool
Please stop looking and book this spot, you will not regret it! Kim provided a list of full things to do for dining, for fun, and much more. Honestly all you need is this spot and Kim’s recommendations. Walking distance to some amazing restaurants with great views and beautiful live music. Don’t have to drive no where to far because everything is less than 5 miles, sombreo beach is beautiful and is just around the condo. Please don’t even bother driving to Key West stay here and enjoy the Keys:) it’s absolutely beautiful and get your own private beach and the pool is so refreshing and CLEAN. No loud music or rowdy crowds, just bliss of relaxation. I’m so happy I booked this spot for our honeymoon and plan to come back for our anniversary or anniversaries. Had a very romantic dinner at the steak and lobster, again Kim’s recommendation!Which was delicious but don’t forget to make reservations. Kim you place had everything we needed. Service was so prompt for everything we needed.

Condo de Paradise/Salt Water Pool/Boat Dock
We are absolutely in love with this place. The views are gorgeous. the grounds were immaculately groomed. There are so many colorful trees and flowers. The pool is slightly heated, which is perfect. Everyone we met was so nice and helpful with recommendations. We got to see the jets fly over a few times, so cool. The kitchen has everything you need to prepare meals and snacks. The beds in both rooms are very comfortable. We hope to stay here again in the future.

Rooftop Penthouse
Our stay at the Penthouse over Duval St was absolutely amazing. Everything was perfect!!! Fully outfitted kitchen, spacious unit, all necessary components and then some. The balcony was so much fun to hang out on in the mornings, afternoons, and after going out on the town at night. Loved the master bedroom so much! Very cavernous, quiet, and dark - good for sleeping. Would definitely stay here again! Highly recommend this place.

Affordable Beachfront Luxury Condo Sleeps 6
Traci’s condo was great in every way! Everything was very clean and the view was amazing. We could enjoy watching the turquoise water and swaying palm trees from almost every room – both bedrooms, living room, kitchen, dining area, or relaxing on the large balcony. Some of the furniture is different in the photos, but my group agrees it is even better now than what you see. Having our own parking space in the garage was much appreciated, too. Traci responded quickly; clear check-in instructions. We would definitely stay here again.

New Listing! Key Lime Paradise/Condo
We Definitely would stay again if we are in the area. The place was exactly as advertised and centrally located. we had a nice relaxing time.

Florida | Waterfront 2BR/2BA w/ Pool + Dock Access
We had a great stay at Jennifer’s condo! It was clean, well-appointed, and had beautiful views of the harbor. The location was perfect—just a short drive to all that Key West has to offer. Jennifer was a proactive host and kept us well informed throughout our stay. Highly recommend!

A Perfect Getaway
We had a wonderful visit in Key west. The place was very clean, close to everything. We enjoyed this place very much and would rent it again. Thank you so very much. Sue and Dave Hopper.
Quick stats about holiday rentals that are kid-friendly in Stock Island
Total rentals
20 properties
Nightly prices starting at
₹17,231 before taxes and fees
Total number of reviews
860 reviews
Family-friendly rentals
20 properties are a good fit for families
Rentals with a pool
10 properties have a pool
Rentals with dedicated workspaces
10 properties have a dedicated workspace
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