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Family-friendly vacation rentals in Islamorada

Find and book unique family-friendly homes on Airbnb

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Popular amenities for Islamorada family-friendly rentals

Family-friendly home rentals with a pool

Top guest favorite
A bright bathroom features a light-colored countertop and a dark wooden vanity. A circular mirror adorns the wall above the sink. A shower curtain with starfish patterns adds a coastal touch, while neatly arranged towels and toiletries are displayed for convenience.
Home in Key Largo
4.97 out of 5 average rating, 33 reviews

Relax and Sun it up in your own rooftop

BrianRating, 5 stars1 week ago
Great place to stay with the family. Nice and clean with a pool and view! Near restaurants, grocery stores and shopping! 100% recommended!
A serene beach scene is framed by swaying palm trees, featuring gentle waves and a clear sky. A playground sits in a grassy area, while a sandy beach offers a dining pavilion. Two kayaks are placed on the shore, adding to the active outdoor vibe.
Home in Marathon
4.82 out of 5 average rating, 34 reviews

Waterfront, dock, easy ocean access, heated pool!

MelissaRating, 5 stars12 months ago
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:))
Guest favorite
Home in Marathon
4.95 out of 5 average rating, 131 reviews

Paradise - Pool, Hot tub, Mini Golf, Dockage, Fish

JenniferRating, 5 stars1 week ago
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!
Superhost
Bungalow in Key Colony Beach
4.67 out of 5 average rating, 6 reviews

Coral Quay-III Canal waterfront,access BEACH club!

JamesRating, 5 stars48 months ago
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!
Guest favorite
Villa in Marathon
4.88 out of 5 average rating, 57 reviews

New Paradise On Sombrero Beach

TonyaRating, 5 stars4 months ago
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.
Guest favorite
The living area features a neutral color palette, with a comfortable sofa facing large sliding glass doors that provide views of the bay. A round dining table and unique lighting fixtures complement the space, while natural light fills the room through sheer curtains.
Townhouse in Islamorada
4.98 out of 5 average rating, 80 reviews

Bayside Townhome in Islamorada with Boat Slip

SteveRating, 5 stars2 weeks ago
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.
An outdoor tiki hut provides a shaded seating area with comfortable wicker furniture. Decorative cushions adorn the sofas, and a hammock hangs nearby. Lush greenery surrounds the space, offering a relaxing spot for gathering or unwinding.
Home in Marathon
4.96 out of 5 average rating, 159 reviews

Vida De Aqua - Water Life!

AntonyRating, 5 stars11 months ago
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!!
Guest favorite
A well-maintained tennis court features a vibrant blue playing surface, with a clear net dividing the two sides. Lush green trees and a bright blue sky are visible in the background, creating a serene environment for outdoor activities.
Condo in Tavernier
4.84 out of 5 average rating, 150 reviews

Bright & Sunny Suite w/ Magnificent Ocean Views

CaseyRating, 5 stars5 days ago
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

Guest favorite
Villa in Islamorada
5 out of 5 average rating, 32 reviews

Anglers Reef Islamorada

NicoleRating, 5 stars1 month ago
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.
A heated swimming pool surrounded by loungers and shade umbrellas is featured within a tropical setting. Lush palm trees and well-maintained gardens provide a vibrant backdrop, with the condo building visible in the distance. The inviting water sparkles under a clear blue sky.
Home in Key Largo
4.83 out of 5 average rating, 24 reviews

Oceanfront Kawama Community,Beach,Pools,Luxury

ClaytonRating, 5 stars9 months ago
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.
Guest favorite
Condo in Islamorada
4.75 out of 5 average rating, 64 reviews

Bayside Condo with Marina, Beach and Pool

HeatherRating, 5 stars2 months ago
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.
A row of four white Adirondack chairs is positioned on fine, white sand, facing the calm turquoise water. A small round table sits in the middle of the chairs, providing a spot for drinks or snacks. The distant horizon features gentle waves under a cloudy sky.
Home in Islamorada
4.88 out of 5 average rating, 26 reviews

Angler's Reef Oceanfront

CorinneRating, 5 stars39 months ago
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.
A serene beach setting features several white, adirondack-style chairs arranged on soft, white sand. Gentle waves can be seen in the background, while greenery lines the shoreline under a clear blue sky.
Home in Islamorada
4.7 out of 5 average rating, 27 reviews

Anglers Reef is Oceanfront, Yellowtail Hse. 2/2.5

AmandaRating, 5 stars15 months ago
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!!
A sunlit sitting area features comfortable seating with soft cushions, surrounded by large windows that provide views of the lush tropical surroundings. A ceiling fan offers a cooling breeze, while decorative elements like plants add to the relaxing ambiance of the space.
Home in Marathon
4.9 out of 5 average rating, 20 reviews

Villa Casa Cayo

AmyRating, 5 stars3 months ago
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.
Superhost
Home in Key Largo
4.72 out of 5 average rating, 71 reviews

Waterfront Ocean Side House with Dock & Boat Ramp

KeithRating, 5 stars3 months ago
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
Superhost
A tranquil coastal scene features clear, turquoise waters gently lapping at the shore. Small rocks and a lone tree are visible along the sandy beach, with a distant island outlining the horizon under a bright blue sky.
Apartment in Key Largo
4.83 out of 5 average rating, 339 reviews

Escape to the Keys!

AmyRating, 5 stars3 weeks ago
Ana was great. The place was exactly as described. Had a wonderful time and would stay here again!

Family-friendly home rentals with Wifi

Guest favorite
The exterior of the home highlights a two-story structure with a spacious paver patio and outdoor seating area. Surrounded by greenery, a white railing encloses the yard, providing a sense of privacy. Large windows are visible, indicating ample natural light within.
Home in Key Largo
4.86 out of 5 average rating, 22 reviews

The Key Largo House

NicoleRating, 5 stars1 month ago
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.
A serene sunset is captured over calm waters, with the sun reflecting warm hues across the surface. Silhouetted against the horizon is a small islet, while distant markers are visible along the waterway, creating a sense of tranquility.
Condo in Tavernier
4.83 out of 5 average rating, 6 reviews

Oceanfront with unbelievable views

MegRating, 5 stars4 weeks ago
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.
Guest favorite
The exterior of a two-story home is displayed, featuring white walls and gray shutters. A welcoming front door is flanked by light fixtures, while vibrant tropical landscaping, including flowering plants, adorns the entrance. A blue sky with scattered clouds is visible above.
Home in Marathon
4.95 out of 5 average rating, 43 reviews

Florida Keys get-a-way in Marathon w/ full dock

MartinRating, 5 stars3 months ago
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!
A bright yellow, two-story home is surrounded by lush greenery and swaying palms. The spacious deck features white railings, offering seating for relaxation. Large windows allow ample natural light, while a paved pathway leads up to the entrance, enhancing accessibility.
Home in Islamorada
4.94 out of 5 average rating, 16 reviews

Islamorada Waterfront Escape

ColeRating, 5 stars11 months ago
Great stay and location. Chris was super helpful with check in and had great communication
Guest favorite
The exterior of the house is framed by lush palm trees, with a spacious deck and outdoor seating visible. A small dock area accommodates watercraft. Bright sunlight enhances the vibrant colors of the greenery and watercraft, contributing to a relaxed coastal atmosphere.
Home in Tavernier
4.93 out of 5 average rating, 42 reviews

Tavernier Bayside

KalieRating, 5 stars3 months ago
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.
Guest favorite
A serene waterfront view is presented, featuring several white Adirondack chairs positioned along a sandy beach. The calm water reflects a clear blue sky, with lush greenery visible in the background, creating an inviting space for relaxation.
Home in Islamorada
4.84 out of 5 average rating, 57 reviews

Oceanfront community 114 Anglers Reef Islamorada

LauraRating, 5 stars2 months ago
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.
Superhost
A bright living area features a futon and a dining table with chairs. Expansive glass doors provide views of the outdoor beach area, framed by lush greenery. Natural light fills the space, enhancing the tranquil atmosphere.
Cottage in Key Largo
4.77 out of 5 average rating, 30 reviews

Cottage w/ Bay View FREE Kayaks, Snorkel & More

JenniferRating, 5 stars3 months ago
my son, my daughter and myself stayed there at the captains cottage for a week after Christmas. it was beautiful and we loved it
Apartment in Marathon
4.7 out of 5 average rating, 43 reviews

Remodeled Sombrero Beach Waterfront Duplex with Dock

Prudence Rating, 5 stars3 weeks ago
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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