
Kid-friendly holiday rentals in Summerland Key
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Top-rated kid-friendly rentals in Summerland Key
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Popular amenities for Summerland Key kid-friendly rentals
Child-friendly house rentals

Key West Paradise
Sharon was an excellent host that answered any of our questions promptly. The place was even better than what the photos showed. Comfortable enough for 7 people to stay for a long weekend. We didn't use the pool, but it was nice to have the option. Easy to get into the gated community, and we didn't struggle to find parking with our rental car. Easy to get to many different popular spots around Key West with rideshare. Convenient to have some convenience stores like CVS within walking distance, and a Publix not too far via car. Only thing I would improve is having more toilet paper and hand soap refills in each bathroom, especially with 7 people staying over a long weekend.

May availability 70ft Dock, Near Beach VACA23-16
Beautiful home located on a beautiful canal. We were able to see so much marine life including manatees. The house was spacious, clean and well located. If we ever get back to marathon we will definitely be looking up the twin palms to stay.

Paradise - Pool, Hot tub, Mini Golf, Dockage, Fish
Although the place wasn’t ready when we arrived, Ryan was a great communicator! He addressed every issue we had (which were NOT within his control) and responded in a timely manner. He offered a fair solution and allowed us to sit back, relax and enjoy paradise! I’d highly recommend and hope to be back sometime soon!

Waterfront Home 37.5-ft dock, Cabana Club Included
We loved our stay! The house was super clean and the back patio was beautiful. We loved the back canal area and saw lots of very cool wildlife and enjoyed fishing right there. Having the kayaks to use was also great. Beds were very comfy and the rooms were spacious. The house had everything we needed. We loved the key colony area. The cabana club was a great space and the house is in walking distance to Sunset Beach, which was beautiful. The whole area is super close to fun things to do and great restaurants. We would absolutely stay here again!

Paradise Ocean Front 4/3Home Heated Pool
Great place to stay! I would come back. was hoping to see manatees but you can't control nature. Great set up for. families with kids.

Kittyhouse on Catherine, Tropical Pool, Parking
Thank you for sharing your beautiful home. We appreciate your wonderful suggestions and thoroughly enjoyed our dinner at El Siboney restaurant. Unfortunately the rain kept us from using the pool but we still had a fantastic time.

NEW PET FRIENDLY Waterfront Single Home-Pool,Beach
The four of us arrived at Mary’s place and we immediately felt right at home. The place was neat and clean and the decor was tropical. The backyard overlooking the canal was a great place to relax and unwind. We loved walking down the block to the Cabana club each afternoon after coming back from local excursions. One of the great benefits was being able to use the Cabana club which had a fantastic pool, hot tub, beach access and a full service bar with great food and drinks with excellent service and a friendly staff!

Casa Calypso 3bed3bath sleeps 8 beautiful decorate
We had a great time at Judy’s airbnb. It was super nice, clean and had really comfortable beds. The pool was right across the parking area, very clean, private and always had chairs available. Over all our stay was great and we will definitely be back.
Kid-Friendly apartment rentals

Bella Vita: 1B/1B Condo for 2 Just Steps off Duval
This was the second time we have stayed at this Airbnb and will return for sure in the future. It is in such a great spot on the southern side of the island close to lots of eateries shops, etc. we loved waking up every morning and having coffee on the porch And the space was perfect for my husband and I to enjoy Easter weekend on the island. I would highly recommend staying here if you get the chance it’s easy and you will feel right at home as soon as you walk in the door.

Duval Balcony Spanky's Retreat
The location on Duval makes everything walkable. We rented a scooter and drove up the ocean side of the island and buzzed all around the island. The scooter rental (Pirate Scooter Rental) was a couple blocks away. We paid to park behind the property, but could have found something for free a few blocks away. The only nit was the occasional Harley or other loud bike that would blast by (trying to make noise) could be heard. The price you pay for literally being on Duval. I looked at a lot of places in this area and no other came close in terms of value (price for amenity). The host was super-responsive, the checkin was flawless, the ac worked great, the shared balcony over Duval was nice.

Studio Near Downtown - The Bartlum
Our first time using Air B&B. My wife loved the experience and location. I liked not having to drive. Parked the car and walked everywhere. Would definitely book again. Thanks for being great hosts!

Capt Craigs Apartment
It's not my normal Keys stay, but this place really exceeded my expectations! Was looking for a short stay. Very reasonably priced, with major conveniences just downstairs/next door: Capt Craig's Restaurant (World-Famous Fish sandwich & great menu), Payfair Supermarket (local family grocer, Boar's Head meats, great sub sandwiches made to order), AND 7-11/Gas station 1 block away. Cute coastal decor, very comfortable. Full kitchen, all necessary items for cooking available. Perfect for a couple & Pet Friendly. There was plenty of available parking and they were able to accommodate the boat & trailer as well. Made everything SUPER easy. You'll need to get on the road for your outdoor activities, but, not to worry, there's so much close by. Thank you for a wonderful stay!

Duval St Apartment w/ Balcony w/parking Adult Only
Greg is a great host and this place is a hidden gem right on Duval Street. What a great find thank you Duval House for a great week in the Keys!

Capt Craigs Apartment
I can't speak more highly of this place; it was better than I could have imagined. I stayed in apartment number 1 and it was wonderful. The host was very attentive and helpful. I'm a light sleeper, but I slept perfectly; I wasn't bothered by any noise. The bed is really comfortable. I have a health condition, and the host helped me with everything I needed. The kitchen was also well-equipped. I highly recommend this place.

#205 Key West Suites
We would be thrilled to stay here again. We have stayed many places while in the Keys however, this was the perfect place to walk about and see what we wanted to see. Everett's place is wonderful; comfortable, clean, and welcoming. Sure, I suppose it could use some updating and better lighting on the stairs, but we don't look at that when we are in Key West! We loved it!! Thank you Everett, and we'l see you again soon. Greg & Kimberly

Cozy Keys Efficiency 8a
Great, quiet place to say. I really enjoyed it.
Child-Friendly Holiday Condos

Oceanfront 3 bed condo Ocean Edge w/ optional slip
Carrie's place was absolutely beautiful! it was so clean, the beds were insanely comfortable, and there were tons of linens and towels for everyone. We very comfortably fit 8 people into the home with no problems. The view from the balcony is absolutely amazing and we were all blown away. Carrie was extremely responsive and friendly. We were here for our wedding and had our wedding party stay here so it was extra magical. The pool and hot tub is super close, elevator to help with our bags, and the resort itself is gorgeous. 10/10 would stay again. We loved it so so much! Don't miss out.

Beach/Docks Avail/3 Pools/Hot tub/Gym/Restaurants
Great experience, great host and accommodations. Hot tub wasn't working while we were there, but repair was delayed over the holiday week which was out of the hosts' control. Very communicative and responsive.

Tropical Escape at Sunrise
Eric’s place was lovely, well maintained, nicely appointed, and immaculate. The 3 of us enjoyed the balcony overlooking the pool. Even though the apartment is near the airport we only heard planes twice in the 4 days we were there. There is a convenient little grocery store on the site and excellent BBQ from a food truck near the pool. Eric responded to our questions promptly. Comfy beds, everything worked and we enjoyed our stay. Would stay here again.

*NEW* Kokomo Views-Pool/Beach
PERFECTION!!! I have so many great things to say about our stay. First, the condo was beautiful and fully stocked. It even had plenty of soap, toiletries, paper products etc to get you started. Yuni was the perfect host and answered all questions and gave clear instructions. The balcony was huge. It was enough for the family to eat and lounge all while enjoying the beach and pool views! Key Colony Beach is a charming community we walked to the sunset multiple nights. My kids aged 10,8,7 did not want to leave. The complex had very friendly retirees and a handful of families with kids. Everyone was super respectful and friendly. The pool was super clean and warm. The beach was groomed each night and the kid had plenty of room to play on the sand and hunt for shells and hermit crabs. Marathon is a great Key to stay on - close to lots of fun activities. We are already planning our next trip and we will definitely rent this condo again! It’s perfect for families!

Key Wes't Best- Upgraded condo 5 mins to Smathers
This place is a gem! The condo was very spacious and it was supplied with everything we needed, no need to buy any extras like other places we have stayed at- Thank you for that! The pool was fantastic! Walking distance to beautiful Smathers Beach. We did not get to do any water activities due to the wind but we had fun exploring around town. Will definitely be returning!

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.

Beachside Unit 37 - Come Relax on the Atlantic!
My little family loved our stay here. We loved the little beach and warm pool. We all wish we could stay longer and would love to come back in the near future!

Sunset South: First Floor 2 Bedroom 1 Bath Condo a
We truly loved our stay and would definitely stay again. The only thing that my family and I were not a fan of was there were no curtains in the living room. So during the day the sun was shining right into the living room and made sitting on the couch rather warm. Also at night we were not a fan that people could possibly see into the place since there were no curtains. Other than that we hope to stay again in the future
Quick stats about holiday rentals that are kid-friendly in Summerland Key
Total rentals
70 properties
Nightly prices starting at
$62 AUD before taxes and fees
Total number of reviews
1.6K reviews
Family-friendly rentals
50 properties are a good fit for families
Pet-friendly rentals
30 properties allow pets
Rentals with a pool
60 properties have a pool
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