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

Waterfront with Boat Lift/Kayaks and Hot Tub
The place was amazing!! plenty of room for our family of 5. All of the fishing equipment was awesome!! From the rods and tackle, to the deep freezer with bait, the extras made the whole trip more enjoyable. Loved the house. It was perfect!!! Will definately be back in the future!! 10 out of 10 would recommend!!

Million Dollar View
This home was everything we expected and more. Stunning location with absolute privacy. The extra long dock was amazing, the pool was fantastic, and the grounds were meticulous. It’s literally your own private resort. Roman, the host, was very quick with communication. He and his wife actually met us when we checked in to see if we had any questions and provided us with an arrival gift. If you have looked at the listing and are thinking of renting it, do it. You will not be disappointed at all. Excellent value all around.

Beautiful Anglers Reef - 2/2.5 - Pool+Marina+Beach
Our first time at Angler's Reef and renting from Doug & Mary and we can't have asked for a better trip. First, Doug & Mary were great in providing everything we needed in advance and very responsive during our stay, couldn't have asked for a better host. The Lucky Lobster is well appointed; had everything we needed. All appliances appeared newer and functioned as they should, overall, the place was very clean and perfect for the five of us. The pool was very nice, and the area offers plenty to do. We rented a boat and went snorkeling at a couple of different sites and then hung out at the sand bar (which is extremely close to Angler's Reef). Anyway, we couldn't have had a better week and highly recommend The Lucky Lobster to anyone visiting Islamorada...

Captain’s Quarters Ahoy Mateys! Florida, Keys
We loved our stay! The host was very responsive and helpful with local recommendations. Great neighborhood and centrally located.

Luxury Heated Pool/Jacuzzi, Games & Nice Backyard.
Exactly what the ad and pictures showed. great getaway for the all 3 generations of family that stayed. I really appreciated the accommodations for the Littles, from the pack and plays to the pool toys. Host was very responsive and answered any questions that popped up. Would definitely stay here again.

Islamorada Waterfront House on Canal w Boat dock
We had a great time. This location is located within Islamorada, which was great. Very close to everything. We fished off the back dock every night. Did not catch much, but was still fun. The place is nice. Many upgrades to an old building. Bed were comfortable. Surprisingly supportive. Kitchen had the bare necessities. Overall, nice place, and we would definitely stay again.

Banana Cabana
We really enjoyed our stay and the location was great, home was cute, clean and well maintained. The property was beautiful and meticulously cared for with amazing views and fun outdoor activities including kayaks, paddle boards, corn hole and "harmless" hatchet throwing! Definitely would visit again

Beach Cottage with pool, Dock and beach access
This house is in a good location and the pool is a definite plus. It was fun watching the neighborhood fishermen bringing in their catches. Being from the west we enjoyed the resident iguanas and the manatee in the channel.
Kid-Friendly apartment rentals

Ocean View Duplex Penthouse | Pool | Vista Two
Beautiful, very clean property with a fantastic location. Excellent proximity to snorkeling, restaurants and other local attractions. Short stroll to excellent walking path that takes you along route 1 with amazing morning views of the beautiful water. Great views all around, in fact. Plenty of soft, plush towels and similarly luxurious bed linens. We had a wonderful family vacation staying at this property.

Beachside Unit 22 - Private Beach on Atlantic
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.

Kawama Lagoon, 3D corner chickee 2bdr , 2 baths
Norma was the most responsive host I’ve ever encountered. Her replies were prompt and she provided outstanding recommendations for local restaurants and entertainment. She checked in with us frequently. Her rental is adorably nautical, clean and well-maintained. I loved her style! She made sure we had everything we needed.

Seaside Vista - Ocean Front 2/1 with dockage
We had to make a very last-minute booking for a two-night stay and were thrilled to find this boat- and pet-friendly spot with space to park our boat trailer. Justin was incredibly quick to respond and made the whole process seamless. The accommodations were clean, comfortable, and exactly what we needed. There was more than enough room for our 24-foot boat, which stayed well-protected from wind and waves. A freshwater hose was conveniently available to rinse the boat off after a day on the water, and the on-site fish cleaning station was a great bonus. The property is just three doors down from Snappers Bar & Grill, where we enjoyed live music, great food, and drinks. We even had the pleasure of meeting the property owners during our stay—truly some of the nicest people you could hope to meet. Overall, a great stay. We’ll definitely be back!

Boho FL Keys Condo
We really enjoyed our stay. The location is great and the view is amazing. It is very clean and very well maintained. Would definitely stay again.

Waterfront Studio 1| Kayaks | Pool |Bay View |Wifi
The shower was amazing. Plenty of hot water and extremely spacious. Studio unit 1 was clean. We used the grill for hamburgers and hot dogs. No one was at the pool. Very private. We enjoyed kayaking. The instructions include pictures to show you how to unlock and lock everything.

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.

MODERN OCEANFRONT CONDO! OCEAN VIEWS! 2 KING BEDS!
Our stay at Fernando's place was great. The listing accurately described the unit, its location, and the amenities. The space was very clean, except for the toilet in the master bedroom being slightly dirty in some places. Overall, we were very satisfied with the place and Fernando was an exceptional host.
Child-Friendly Holiday Condos

1BR - Key Largo Sun & Sand Hideaway
Stayed at Vanessa’s place twice while visiting the Keys. Quiet, clean and private. A great host and would definitely stay again next time a visit. Easy access to everything off the highway and great amenities with the pool and beach nearby. 10/10.

Reel Large END Unit in Ocean Point Suites
very kind and flexible hosts. Let us check out an hour after checkout time and we're also very communicative, friendly and service oriented. definitely recommend

Gorgeous lagoon-front 2BR Townhouse with 2 pools
This place was just what we needed. It was the perfect size for our 4 plus a dog for 2 nights. It’s located in a nice community and close to a lot. I would stay here again!

Million dollar view in Key Largo!
The condo was very nice. Lots of room, clean and easy to access. We loved the balcony, and spent a lot of time there. We enjoyed the kayaks a couple of different times as well. Our first time to The Keys and we enjoyed this spot.

Slip, Ramp, Pool, Trailer Parking, Bait Freezer
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.

Studio with Balcony, Kitchen, Open Living Space
My husband and I chose this place for part of our honeymoon, and we were so happy we did! We absolutely loved it, even more than the resort we paid double the price for in Key West. Our room was clean and very comfortable. The pool area was equally clean, never too crowded, and offered a really peaceful atmosphere. Having a full kitchen was a huge benefit for us, it allowed us to save money on meals and enjoy some home-cooked food. We were also incredibly lucky to have a beautiful view of the water from our room. We loved waking up each morning, making breakfast in our kitchen, and eating it on our little patio while enjoying the view. There’s lots of cool stuff to do in Islamorada, and the location of this place made it easy to explore everything. We had such a wonderful experience and would love to return someday!

BEAUTIFULLY DESIGNED OCEANFRONT CONDO
We really enjoyed our stay Beautiful condo extremely clean clear instructions wonderful place to stay pool and hot tub area are amazing. You can swim anytime which is really nice. Most places the pool closes at dusk. There is a nice poolside little restaurant and also a restaurant right by the beach area really convenient would go back there anytime

Sugar Cane - Florida Keys tropical retreat
Great stay in the Keys, easily accessible to all that the area has to offer. Nice amenities in the community as well. Would stay again!
Quick stats about holiday rentals that are kid-friendly in Islamorada
Total rentals
60 properties
Nightly prices starting at
$134 NZD before taxes and fees
Total number of reviews
1.4K reviews
Family-friendly rentals
60 properties are a good fit for families
Pet-friendly rentals
30 properties allow pets
Rentals with a pool
40 properties have a pool
Destinations to explore
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- Everglades National Park
- Sombrero Beach
- John Pennekamp Coral Reef State Park
- Zoo Miami
- Bahia Honda State Park
- Coral Castle
- Cannon Beach
- Biscayne National Park
- Conch Key
- Calusa Beach & Loggerhead Beach
- Everglades Alligator Farm
- Theater of the Sea
- EAA Air Museum
- Long Beach
- Cocoa Plum Beach
- Far Beach
- Sea Oats Beach
- Monkey Jungle
- Horseshoe Beach
- Windley Key Fossil Reef Geological State Park
- Keys' Meads
- Long Key State Park