
Family-friendly vacation rentals in Islamorada
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Top-rated family-friendly rentals in Islamorada
Guests agree: these family-friendly homes are highly rated for location, cleanliness, and more.
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Popular amenities for Islamorada family-friendly rentals
Family-friendly home rentals with a pool

Relax and Sun it up in your own rooftop
Great place to stay with the family. Nice and clean with a pool and view! Near restaurants, grocery stores and shopping! 100% recommended!

Waterfront, dock, easy ocean access, heated pool!
This house was a perfect spot for my partner and I and Cooper our pup. swam in the pool, sat in jacuzzi, paddle boarded ,kayaked, road the bikes, ect. we brought our boat down but unfortunately had a few issues with it so wasn't able to go out fishing as much as we'd liked. but there was plenty to do at and around this beautiful place. would definitely come back in the future:))

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!

Coral Quay-III Canal waterfront,access BEACH club!
We had an amazing time at this property. The location was couldn't get any better. We brought our boat and property was perfect for that. We are already starting to plan for next year!

New Paradise On Sombrero Beach
This place had everything we needed for a relaxing family vacation prior to the crazy Holiday season. we only had 6 people but it would easily accommodate more. Monica was responsive to any questions or concerns. The location was perfect. Easy access to sombrero Beach and Marathon amenities: bars, restaurants, and activities. we were able to experience a turtle release on Sombrero Beach from The Turtle Hospital. Highly recommend renting from Monica again and on Marathon Beach.

Bayside Townhome in Islamorada with Boat Slip
Claire had an emergency which caused her to forget to contact house cleaning but she was awesome to work with and went over and above to make it right when we told her of the problem. You won’t find a more beautiful private place to stay. Location is as good as it gets. Claire was a great host and we really appreciated it.

Vida De Aqua - Water Life!
We came for our second stay at Judy’s lovely house. It’s very clean and very comfortable and in a great location. The tiki hut has very comfortable chairs and is a great place to unwind with a drink in the evening. Highly recommended!!

Bright & Sunny Suite w/ Magnificent Ocean Views
I can't say enough about our experience here at Tavenier. Largo was extremely responsive and helpful. The communication honestly could not be improved at all. The condo was beautiful and met all of our needs. It is close to several attractions as well as grocery stores and coffee shops. We would love to stay here again the next time we return to the Keys! You can't go wrong with this airbnb choice.
Family-friendly home rentals with air conditioning

Anglers Reef Islamorada
Our family of 5 loved our time in Islamorada. The community was beautiful and quiet. It was definitely mostly retired couples but everyone was friendly with our young kids. The condo was bigger than the pictures made it seem- we had more than enough space. Everything was clean and we had everything we needed.

Oceanfront Kawama Community,Beach,Pools,Luxury
Andrew’s place was very clean, and he is a very hospitable host! We thoroughly enjoyed our stay, and will be reaching out to him when we come back to the Keys again! I lived in Marathon FL for a long time, and know the keys well. It is rare to find a host as good as Andrew down there! I HIGHLY recommend staying at his place if you’re considering visiting. Great, private Yacht club with a boat ramp/marina, hidden right off the main drag of Key largo.

Bayside Condo with Marina, Beach and Pool
The photos and amenities were exactly as described. The home was comfortable and Glenn is amazingly responsive. His air blasts cold, the pool was heated and the grounds were nice.

Angler's Reef Oceanfront
My friend and I stayed at this lovely house in a well maintained community. The house is clean and very nice. The owner was very responsive. We had no issues during our week stay. The community pool was fantastic. We grilled a few nights and took advantage of the great restaurants within 10 minutes away. Highly recommend unit and location.

Anglers Reef is Oceanfront, Yellowtail Hse. 2/2.5
We had a fantastic stay here during our week in Islamorada. The house was incredibly clean, uncluttered, and had a nice feel. The road noise was pretty much constant, which we were prepared for ahead of time based on other reviews. But noise makers were provided and helped a bit. There were full sized soaps in the kitchen/bathrooms. There were plenty of cleaning supplies in the kitchen including garbage bags, Clorox wipes, and dishwasher detergent. Beach/pool towels were also provided. All of these amenities make it easier when traveling by air. The property had paddle boards and kayaks for use on a first come first serve basis. All 5 of us, my hubby, our three girls ages 13, 19, and 21 had a fantastic time paddling around nearby. Watching the sunset was particularly lovely on the water. There were some fantastic restaurants nearby that were walkable and within a 5-10 minute drive. If we were to come back to the area, we would definitely consider staying here again. Thank you!!

Villa Casa Cayo
This home was just what my family needed for our vacation! We all loved relaxing in the outdoor living room surrounded by greenery. We also enjoyed swimming in the pool and kayaking through the canals and Boot Key. We made most of our meals due to dietary restrictions, and the kitchen here was adequate. The location in Marathon is excellent! It was just a 5-minute walk to Sombrero Beach, so we never had to worry about parking. We could easily drive to all the activities we wanted to do in the area, too.

Waterfront Ocean Side House with Dock & Boat Ramp
stayed for 4 weeks, great when two couples are traveling together quiet location, near great restaurants, very clean, lots of toys to use very ell priced for area

Escape to the Keys!
Ana was great. The place was exactly as described. Had a wonderful time and would stay here again!
Family-friendly home rentals with Wifi

The Key Largo House
Wonderful stay in Key Largo! Great location with many close dining options for boaters. Deep water dock (12 feet by our depth finder). You can catch mangrove snapper right off the dock. We saw a manatee in the canal! I would recommend staying here, we had a wonderful time.

Oceanfront with unbelievable views
The view is beautifully tropical with the ocean water alternating turquoise blues! The white sand beach, palm trees and sparkling pool added to the ambience. The condo had everything we needed, beach towels, umbrella and beach chairs were a plus. There is a high school next door so you can expect high school activities. As it was our first experience in the keys, the location worked well for us. We could go back and forth across all the keys and experience what they had to offer.

Florida Keys get-a-way in Marathon w/ full dock
It was an unforgettable week in Maria and Johnny's house. The house was very clean and beautifully furnished. Each of our three children had their own room in which they felt very comfortable. Our bedroom had a large terrace where my wife could do yoga in the morning sun. The kitchen and living room were really well epuiped and terrace with the hot tub were just right for a relaxing family holiday. Nothing was missing. Communication with Johnny was easy and quick. He gave us great ideas for activities and restaurants in the area. Thank you for that. We can highly recommend Maria and Johnny's accommodation!

Islamorada Waterfront Escape
Great stay and location. Chris was super helpful with check in and had great communication

Tavernier Bayside
My family and I stayed here for the whole month of January and, despite the weird weather, we had a great time! Naylen's place was perfect for us and she was very responsive to any minor issues we had. We loved the backyard setup with the pool, fish cleaning station, ice machine, dock, outdoor grill and surround sound. Having access to the neighborhood's private boat ramp was a huge plus! The landscaping is done very well to make the backyard feel very private. The house is within walking distance to a cute restaurant called Crooked Palm and close driving distance to a bunch of other really good restaurants. It's also close to Founder's Park which we had free access to. Our kids enjoyed the park's beach and playground. Overall, Naylen's place is a great setup and we would highly recommend.

Oceanfront community 114 Anglers Reef Islamorada
We loved this house. It was great for our family of 5. The pool area was great, and the access to the canoes and paddle boards and fishing equipment was also great. We were in walking distance to a couple of nice eateries and we got a cab to the ones that weren't within walking distance. The instructions were clear and covered everything that was required. The only slight complaint would be the road behind the house was a little noisy.

Cottage w/ Bay View FREE Kayaks, Snorkel & More
my son, my daughter and myself stayed there at the captains cottage for a week after Christmas. it was beautiful and we loved it

Remodeled Sombrero Beach Waterfront Duplex with Dock
Just what we needed for winter break , loved having coffee in the morning on the canal, hammock very relaxing, liked the open living space.
Quick stats about vacation rentals that are family-friendly in Islamorada
Total rentals
610 properties
Nightly prices starting at
$80 before taxes and fees
Total number of reviews
4.9K reviews
Pet-friendly rentals
270 properties allow pets
Rentals with a pool
420 properties have a pool
Rentals with dedicated workspaces
330 properties have a dedicated workspace
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