Kid-friendly vacation rentals in Summerland Key

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Popular amenities for Summerland Key kid-friendly rentals

Kid-friendly house rentals

Guest favorite
Home in Cudjoe Key
5 out of 5 average rating, 16 reviews

Keysie Does It at Cudjoe Key

MeganRating, 5 stars3 months ago
We absolutely loved our stay! Our checkin was smooth and flexible. The home was squeaky clean, linens and beds were unbelievably soft and comfortable, and there were more supplies/ amenities in the home than listed. We felt right at home and would love to come back! Absolutely 5 star place!
Guest favorite
Home in Cudjoe Key
4.98 out of 5 average rating, 47 reviews

Waterfront 35’ Dock,80’ pool,20 min Key West

KimberlyRating, 5 stars1 week ago
We had a great stay! House was neat and tidy and in a great location.
Superhost
Home in Summerland Key
4.58 out of 5 average rating, 84 reviews

OCEAN FRONT PARADISE/ PRIVATE DOCK/AWESOME VIEWS

SarahiRating, 5 stars1 month ago
We had a great long weekend at Alex house! You are provided with a starter kit, so you may need to buy extra supplies if planning to stay in at property. House vibes are very keywest. Winn Dixie very close and Bahia Honda state park was close by and beautiful to spend the day if looking for something to do. Keywest about 40 min drive, easy to get around. Had plenty of blankets, pillows and accommodated 10 of us— we did bring an air mattress which I would recommend as sofa beds are not the most comfortable. Has a beautiful backyard which we spent a lot of time on and yummy walkable restaurant. Plenty of parking. Host was very responsive and checked in with us to make sure check in was smooth.
Superhost
Home in Cudjoe Key
4.88 out of 5 average rating, 59 reviews

Cozy 2 br/2 bath home in Cudjoe

MariannRating, 5 stars1 month ago
Marcela's place was exactly as described and very clean. One master bedroom with master bath, and another bedroom with a twin/trundle bed, and sofa in living room. Kitchen had good amenities with cutlery and glasses, etc. We didn't use the washer but the dryer was very handy for drying bath towels and pool towels. We sat outside in the back yard the first night and heard a mysterious animal call, we thought it was a bird but then using google we found out it was a tokay gecko! So cool. We used the large saltwater pool which was very very nice. It's just a short drive to several great restaurants in neighboring keys, and we made a day trip to Key West which was awesome! I recommend Tonio's Seafood Shack & Tiki Bar, great key lime pie. Forks & Stix is a great little sushi place with great lemonade, Island Fish Company in Marathon had a great outdoor vibe right on the water. Best beach is Bahia Honda State Park. Note there is a $125 community fee upon check-in to the resort.
Guest favorite
Home in Cudjoe Key
4.95 out of 5 average rating, 20 reviews

Sea Turtle Cove

ThomRating, 5 stars1 month ago
Philip's listing described the place perfectly. Zero unexpected surprises and it had absolutely everything to make our vacation super enjoyable. When it comes to location, so much to do in under 30 minutes. Smack dab in the middle when it comes to driving to Marathon or Key West. It was also great to be able to keep a boat right outside and to have a marina as part of the park. Access to great places to fish are 15-30 minutes away.
Guest favorite
Home in Key Colony Beach
4.95 out of 5 average rating, 117 reviews

Waterfront Home 37.5-ft dock, Cabana Club Included

LaurenRating, 5 stars3 days ago
Clean house, well decorated, great location and responsive hosts! It’s also a plus that they accept pets for a reasonable pet fee. Key Colony Beach is a great location and this is a lovely little home. Book with confidence!
Superhost
Home in Cudjoe Key
4.88 out of 5 average rating, 32 reviews

Waterfront FL Keys Cottage @ Venture Out

ElizabethRating, 5 stars6 days ago
Great location, easy access to everything, lots of amenities on the community.
Guest favorite
Home in Cudjoe Key
4.93 out of 5 average rating, 60 reviews

Betty's Place

EmilyRating, 5 stars2 weeks ago
Honestly I was super impressed with how quick Jacqueline responded and how smooth the check in went. Betty’s Place was such a beautiful home and very clean and spacious. We had an amazing time and can’t wait to plan another keys trip at Betty’s place!

Kid-friendly apartment rentals

Superhost
Apartment in Key Colony Beach
4.84 out of 5 average rating, 115 reviews

Beachside Unit 22 - Private Beach on Atlantic

JamesRating, 5 stars3 weeks ago
Very nice condo in key colony beach, affordable, great stay for a family. Clean rooms, nice pool, nice private beach area, will bring family down again.
Guest favorite
Apartment in Key West
4.9 out of 5 average rating, 107 reviews

Duval Street Suites full kitchen Old Town with hea

RichardRating, 5 stars6 days ago
The location of the apartment could not have been in a better place. Easy access to the apartment from the rear of the building through the parking lot in Pool area to the front of the apartment on Duval Street. The apartment was immaculately kept. The bed and the pullout couch was very comfortable
Guest favorite
Apartment in Key West
4.84 out of 5 average rating, 800 reviews

Duval Balcony - Street Suite

StaceyRating, 5 stars2 weeks ago
Our stay at Street Suite was enjoyable from the time we checked in to the time we left. We enjoyed people watching from the balcony overlooking Duval Street. The room was perfect for us -its seating is a tad different from the photo, with just one love seat and a bistro table and chairs. It still worked and did not make a difference to us since we spent such little time in the room. There is a golf cart, bicycle, and scooter place right across the street. A key lime and ice cream shop below for those late-night munchies. It's a perfect location for an airbnb. We are already planning our next visit!
Top guest favorite
Apartment in Key West
4.98 out of 5 average rating, 505 reviews

Bella Vita: 1B/1B Condo for 2 Just Steps off Duval

ReneeRating, 5 stars5 days ago
Bella Vita was impeccable! It was exactly as described and like the pictures. Eric and Kelly were communicative and very prepared hosts. This was our best Airbnb experience thus far, and best stay out of many in Key West. We will be back to Bella Vita. Everything was perfect!
Top guest favorite
Apartment in Key West
4.95 out of 5 average rating, 319 reviews

Honeymoon Hideaway, King bed, Private Deck & Spa!

EmilyRating, 5 stars2 weeks ago
This was our first time traveling to Key West and we weren’t sure what to expect. I can’t say enough great things about Center Cottage Inn. They went above and beyond our expectations and it was the perfect place to experience a lot of the wonderful things the island has to offer. The cottage we stayed in was fully equipped for all of our needs and was tiny in the best way. It had a lot of great storage, ample towels (both for bathing and the pool), fully stocked kitchen (we opted to make our own breakfast each day), and lots of thoughtful details like a portable speaker, bug spray, charging ports and more. Naomi was super responsive and helpful. We were able to leave our bags on the premises as our departure flight wasn’t until late afternoon. This was a game changer as we were able to enjoy our last day without carrying luggage around. If you want to feel like locals this is the place for you.
Superhost
Apartment in Key West
4.84 out of 5 average rating, 1,338 reviews

At Mine | Key West Suite steps from Duval Street

KristinRating, 5 stars6 days ago
This is a secret little gem of a place to find! Quiet, perfect walking distance to everything! Very thankful I found this place. Everyone was friendly! The pool makes you feel like you’re in a tropical jungle. The setting is just right! I would recommend this place to everyone. We will definitely be back.
Guest favorite
Apartment in Key West
4.85 out of 5 average rating, 237 reviews

Studio Near Downtown - The Bartlum

CrystalRating, 5 stars1 week ago
Conveniently located spot that is walking distance to Duval and all the nearby restaurants and sights!
Guest favorite
Apartment in Marathon
4.97 out of 5 average rating, 105 reviews

Beachfront Condo w/ Ocean Views in Marathon

AnneRating, 5 stars1 month ago
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.

Kid-friendly condo rentals

Superhost
Condo in Key West
4.87 out of 5 average rating, 147 reviews

Rooftop Penthouse

ShaunaRating, 5 stars2 weeks ago
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.
Superhost
Condo in Duck Key
5 out of 5 average rating, 38 reviews

Oceanfront and Sunrise Views!

StephenRating, 5 stars3 weeks ago
We had an amazing stay in this wonderful Condominium! The host was absolutely fabulous - super responsive, friendly, and made sure we had everything we needed. The apartment itself was clean, comfortable, and perfectly located. The whole experience was top-notch, and we highly recommend this place to anyone looking for a great stay. Thanks again to the host for making it so special!
Guest favorite
Condo in Key West
4.89 out of 5 average rating, 142 reviews

Tropical Escape at Sunrise

MalloryRating, 5 stars3 weeks ago
We enjoyed our stay! A little outside of the heart of Key West so it was very quiet. This place does have a unit above, luckily we were not bothered by any sort of upstairs noise. Would recommend!
Superhost
Condo in Key West
4.87 out of 5 average rating, 201 reviews

Florida | Waterfront 2BR/2BA w/ Pool + Dock Access

JustinRating, 5 stars1 month ago
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!
Guest favorite
Condo in Key West
4.89 out of 5 average rating, 168 reviews

A Perfect Getaway

DavidRating, 5 stars2 weeks ago
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.
Guest favorite
Condo in Key West
4.95 out of 5 average rating, 152 reviews

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

TinaRating, 5 stars3 days ago
This listing was everything and more! The space was very clean, and provided all of the necessary amenities. As far as location…top tier. All the major attractions and beaches were a short 15 minute drive. Chris was responsive when I reached out. Truly a gem, and I would recommend this space again and again.
Top guest favorite
Condo in Marathon
4.96 out of 5 average rating, 102 reviews

Slip, Ramp, Pool, Trailer Parking, Bait Freezer

AlexRating, 5 stars2 weeks ago
Absolutely perfect for a honeymoon getaway, quiet perfect amount of space for us, the set up was great with 2 bathrooms and a huge walkin closet, the couches were super comfy, the TV was big enough to see from across the room, we enjoyed everything about it. Got to meet some of the neighbors and they were all very welcoming and enjoyed talking to them. Scott had some great local recommendations and we enjoyed everything.
Guest favorite
Condo in Key Colony Beach
4.91 out of 5 average rating, 306 reviews

Coastal Key Colony Beach Condo, Oceanfront Complex

ShaniaRating, 5 stars3 weeks ago
We stayed here for a week and it was such a blast, didn't want to leave! The beach is quiet and peaceful and there are plenty of restaurants nearby. The condo was very clean and nice too. Kim's instructions were very clear, and I never had to ask any questions. I'm hoping we will be back next year!

Quick stats about vacation rentals that are kid-friendly in Summerland Key

  • Total rentals

    70 properties

  • Nightly prices starting at

    R720 ZAR 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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