Kid-friendly holiday rentals in Summerland Key

Find and book unique family-friendly rentals on Airbnb

0 of 0 items showing
1 of 3 pages

Popular amenities for Summerland Key family-friendly rentals

Kid-friendly house rentals

Guest favourite
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.
Guest favourite
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.
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.
Superhost
Home in Key Largo
5 out of 5 average rating, 4 reviews

Newely Renovated 3/2-private pool/dock/cabana club

OliviaRating, 5 stars2 weeks ago
Absolutely amazing place to stay! Dennis is amazing and had several great recommendations for us to eat and do! The dock out back was beautiful and we were even able to see manatees! The pool was a GREAT addition and my family wouldn’t have wanted to explore the Keys any other way! The neighbors are also friendly and great to talk to! Overall beautiful place! My family and I would stay again!
Superhost
Home in Cudjoe Key
4.89 out of 5 average rating, 38 reviews

Lower Keys Paradise

NateRating, 5 stars2 weeks ago
We needed to be near summerland key for work all week, but no short-term airbnbs on thT key. This was key adjacent, the rental was comfortable, the pool and hot tub were great for unwinding at the end of each work day.
Guest favourite
Home in Marathon
4.92 out of 5 average rating, 12 reviews

NEW! Private Pool, 50’ Dock, Kayaks, Waterfront

HansRating, 5 stars3 weeks ago
Loved every minute of our time here. Communication was excellent before during and after our stay and the house was superb. Highly recommended
Top guest favourite
Home in Key Colony Beach
4.96 out of 5 average rating, 105 reviews

Captain’s Quarters Ahoy Mateys! Florida, Keys

BrandyRating, 5 stars3 weeks ago
We loved our stay! The host was very responsive and helpful with local recommendations. Great neighborhood and centrally located.

Family-friendly apartment rentals

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

Beachside Unit 22 - Private Beach on Atlantic

JamesRating, 5 stars2 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.
Superhost
Flat in Key West
4.88 out of 5 average rating, 1,502 reviews

At Mine | Lovely Suite steps from Duval Street

JesseRating, 5 starstoday
We had a fantastic stay at Tranquility Guest House — we were able to check in early and everything was already clean and prepared for us. The host was very responsive and helpful with messaging which was reassuring. The pool is also clean, quiet, and private. Overall this is a great value for the money and the location is perfect!
Guest favourite
Flat in Key West
4.9 out of 5 average rating, 107 reviews

Duval Street Suites full kitchen Old Town with hea

RichardRating, 5 stars2 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
Superhost
Flat in Key West
4.77 out of 5 average rating, 361 reviews

Key West - Sunrise ❀ The Green House

ChadRating, 5 stars1 month ago
Great spot, super close to everything but never disturbed by late night noise. Balcony is awesome to have !
Guest favourite
Flat in Key West
4.84 out of 5 average rating, 799 reviews

Duval Balcony - Street Suite

BrittanyRating, 5 stars2 weeks ago
The place is exactly as it’s shown on the listing! Super cute and quaint! It’s got a cute deck to people watch from when you need a moment to relax from all the fun of being in the middle of duval! And Tom was a great host! Super friendly and very easy to reach when needed. Will definitely book with him next time we visit!
Top guest favourite
Flat in Key West
4.98 out of 5 average rating, 502 reviews

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

LeslieRating, 5 stars2 weeks ago
We had a really lovely stay at this space! It is as advertised and very clean. We used the kitchen every day and sometimes twice a day. What’s great about this space is that the patio and seating area is always in the shade…. at every hour of the day!
Guest favourite
Flat 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.
Guest favourite
Flat 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.

Family-friendly apartment rentals

Superhost
Apartment in Key West
4.83 out of 5 average rating, 276 reviews

La Dolce Vita, Old Town Steps to Duval! 3 blks bch

MichaelRating, 5 stars2 weeks ago
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!
Superhost
Apartment in Key West
4.87 out of 5 average rating, 146 reviews

Rooftop Penthouse

JasonRating, 5 stars1 month ago
The stay was perfect for me and my friends to experience Key West! Being right on Duval made it easy to walk to all the restaurants and bars in the area.
Guest favourite
Apartment in Key West
4.9 out of 5 average rating, 141 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!
Guest favourite
Apartment in Key West
4.95 out of 5 average rating, 151 reviews

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

NancyRating, 5 stars1 week ago
Enjoyed our time at Chris’s place. Plenty of towels and the kitchen was well furnished. Wonder if an air purifier might help as a few of our allergies kicked in when we were inside. All in all a great vacation
Top guest favourite
Apartment 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 favourite
Apartment in Key West
4.9 out of 5 average rating, 207 reviews

"Abaco" Key West • 2/2 End Unit Waterfront+Dockage

SusanRating, 5 stars1 week ago
The condo was exactly as pictured, clean, quiet and close enough you could walk to some things, I would suggest taking an uber to downtown especially during the summer. The restaurant/bar Mac’s next door has good food. The noise others complain about we could not really hear inside the condo, so not sure why that was mentioned by others. We had a great time, ate some great food and explored a lot of what Key West has to offer. We would definitely stay in this condo again. Thanks Jennifer for sharing your beautiful place with us.
Guest favourite
Apartment in Key Colony Beach
4.91 out of 5 average rating, 305 reviews

Coastal Key Colony Beach Condo, Oceanfront Complex

VictoriaRating, 5 stars1 month ago
Kim’s condo was PERFECT for our stay, and Kim was an outstanding host. The apartment was clean, comfortable, and well stocked. It is a rarity to find reasonably priced lodging in the keys that has its own charming private beach!! I appreciated that we had access to a kitchen to cook in, outdoor gas grills, and a laundry area (takes $2 in quarters to cycle- bring a little change!). Kim gave us great recommendations on things to do in the area, and even gave me a tour of her incredible garden beds including a bed of pineapple plants! We can’t wait to return.
Superhost
Apartment in Marathon
4.85 out of 5 average rating, 238 reviews

Sombrero Beach Tropical Getaway

CaseyRating, 5 stars1 month ago
This was our 2nd stay at this place. We love all the resort has to offer and the location makes it easy to get to places in Marathon

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

  • Total rentals

    70 properties

  • Nightly prices starting at

    ₹3,443 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

Destinations to explore