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

Avail. Now! 70ft Dock, Close to Beach VACA23-16,
Beautiful home located on a beautiful canal. We were able to see so much marine life including manatees. The house was spacious, clean and well located. If we ever get back to marathon we will definitely be looking up the twin palms to stay.

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!

Waterfront Home 37.5-ft dock, Cabana Club Included
Great family friendly island, all homes have canal access for boating. Quite, private and had a great time

Island Breeze
Thank you Maddy for sharing your beautiful home with us for the week! It was absolutely what we needed sunshine and relaxation. The whole family enjoyed the pool, hot tub, and pool table. The grill being there was a great addition. The kids could continue to have fun while food was cooking…

Paradise Ocean Front 4/3Home Heated Pool
We had a 5 star stay at Isabella’s Airbnb home! We had 10 guests and all had a place to sleep, place to sit and eat if we all wanted to sit together at the dining table and plenty of room there! We loved her home and our stay there!! Isabella remembered that we were there on vacation celebrating our mom’s 80th birthday and went out of her way to buy a key lime pie and balloon to have waiting for us/my mom when we arrived! That was very thoughtful and sweet of her!! Thank you for sharing your home with us!!!

NEW PET FRIENDLY Waterfront Single Home-Pool,Beach
Mary and Ted took wonderful care of us. Just a text away ! Loved walking to Cabana Club and spending time on Beach. The location on quiet street with nice neighbors. Great location for Fishing and tying boat up to their dock. Added plus bait freezer. Highly recommend this property.

Sunsets In Palms Paradise
The house was great, and the backyard amazing! Dolphins right next door, lots of shore birds, and fishing right from the dock. Hot tub under the stars, kayaking in the morning. Really great place to spend part of our spring break

Golf Coast Oasis
We really enjoyed our week at Gulf Coast Oasis! The house was lovely, well-stocked, and great for our family of 5. We very VERY much enjoyed the pool and appreciated being able to heat it. Loved using the bikes and kayaks. Ate on the screened in porch. Madelyn was very helpful and responsive both in advance of and during our trip. Great stay! The only "negative" was the noise from the nearby airport -- not disruptive but worth noting.
Family-friendly apartment rentals

Beachside Unit 22 - Private Beach on Atlantic
Key Colony Beach is truly the gem of the Florida Keys. Staying at Cindy's apartment in the Continental was the perfect fit for my husband and I. The private beach was clean, easy to access, and just steps from the accommodation. The overall vibe here was quiet and peaceful, and the apartment had all the amenities we needed for a 5-day stay. Cindy's space is very clean and well-appointed. This location is perfect for morning walks around the immaculate and safe neighborhood, or short jaunts to Key Colony Inn or Havana Jack's for dinner/drinks. Honestly now, you're already here! What's your hurry? :)

Kawama Lagoon, 3D corner chickee 2bdr , 2 baths
Norma’s place was great! Norma was super helpful with recommendations, quick communication, and her place was comfortable & perfect for the 4 of us (2 couples). Can’t wait to come back.

Waterfront Studio 2| Couples Oasis | Kayaks | Pool
My best friend and I stayed at the marina for 2 nights, and the stay was great. It was very clean and the surroundings were private and quiet. We loved being able to grab the paddleboards and go around. The host was super responsive and attentive, and overall, we had a fabulous time. Would definitely recommend.

Best Place to see the sunset
Spacious and comfortable condo for a family of four! We enjoyed the pools, swimming lagoon, pickleball courts, and the sitting areas on the ocean. The kitchen is well-appointed and the attached private laundry room was a bonus. The beds in both rooms were very comfortable. We regularly did the 5-minute drive to Pennekamp State Park for the sandy beach, rental kayaks and paddle boards through the mangroves, and snorkeling trips to the reefs and shipwrecks. We also enjoyed the local fish markets in the marina just a short walk from the unit. We will stay here again.

Apartment in Big Pine
This little studio apartment in big pine is PERFECT for a couple for a few days or week. We loved the big windows on 3 sides, with a great view of sunset & the marsh. We also loved the private and spacious balcony that has a view of sunrise. It is very peaceful and quiet, with the deer coming by every morning and evening. There is no kitchen (which was fine with us) but there is a coffee pot and 2 mugs. The bathroom is roomy for a studio and has closet space available. The sunset view from this place honestly was my favorite part of our trip. I would stay here again if I traveled to the keys in the future.

Escape to the Keys!
Ana was great. The place was exactly as described. Had a wonderful time and would stay here again!

Beachfront Condo w/ Ocean Views in Marathon
This is a beautiful ocean-front condo!! It is equipped with everything needed to spend a week or many weeks. The view is incredible, the beach is very nice and walkable. It is quiet, relaxing and the pool is at least 85 in January!! Enjoyed our week very much and hope to come back for a few weeks next time!!

3. Oceanside Retreat with Canal Access, Key Largo!
I have so many great things to say and don't know where to begin. It's everything I wanted and more! we'll managed/great area! You will love it! I love how modern, very functional and they communicate well! I also stayed cause the pricing was not outrageous. I will stay there again if I come back to the Florida Keys!
Family-friendly apartment rentals

Beach/Docks Avail/3 Pools/Hot tub/Gym/Restaurants
Great experience, great host and accommodations. Hot tub wasn't working while we were there, but repair was delayed over the holiday week which was out of the hosts' control. Very communicative and responsive.

2BR - Key Largo Sunshine Getaway
Great place for a family. The pool and beach were ideal for kids and the little tiki bar was great for us. The surroundings were lush. We would stay here again.

*NEW* Kokomo Views-Pool/Beach
PERFECTION!!! I have so many great things to say about our stay. First, the condo was beautiful and fully stocked. It even had plenty of soap, toiletries, paper products etc to get you started. Yuni was the perfect host and answered all questions and gave clear instructions. The balcony was huge. It was enough for the family to eat and lounge all while enjoying the beach and pool views! Key Colony Beach is a charming community we walked to the sunset multiple nights. My kids aged 10,8,7 did not want to leave. The complex had very friendly retirees and a handful of families with kids. Everyone was super respectful and friendly. The pool was super clean and warm. The beach was groomed each night and the kid had plenty of room to play on the sand and hunt for shells and hermit crabs. Marathon is a great Key to stay on - close to lots of fun activities. We are already planning our next trip and we will definitely rent this condo again! It’s perfect for families!

Key Lime Breeze Retreat!
Kim's place was perfect for our extended family. The full unit (kitchen, lounge, bathroom, and bedroom) downstairs was perfect for my parents to stay while my family of 4 plus my sister stayed upstairs where there is another kitchen and lounge as well as 2 bedrooms. Facilities in the complex were fantastic with a huge pool, tennis and pickle ball courts, and clubhouse. The location was great to get anywhere in Key Largo as well as the rest of the Keys. Last, but definitely not least, the hosts were extremely responsive and helpful with all the questions and things that came up during the stay. Would definitely recommend and stay again if we are back in the Keys.

Waterfront Spacious Condo Key Largo #4, 10% Off 7+
The first half of our stay went extremely well and there was plenty of space to park our boat. I would definitely stay again.

Luxurious Suite+Open Ocean Views+Pool & Cabana Bar
This place checked all the boxes! The location of this particular unit was awesome. Close to the pool, but not too close. A short walk to the beach area, and those views from the balcony are second to none. Largo is very responsive and very easy to communicate with. Tavernier Key is the perfect location to many activities. Our family misses this trip already.

Spring-Summer Deals! LUX Oceanfront 1300sf Condo!
Great place just a short distance off Highway 1 and just steps from a nice heated pool. The salt water slough was a big hit for the kids swimming with the fish and the sunrise was amazing. I would definitely book again.

Key Largo Sunrise Resort Style Ocean Pointe 5315
Sean and Denise were amazing hosts. They were extremely responsive and very flexible with check-in and check-out. Their place was perfect and extremely clean. The beds were very comfortable as well. The grounds are great with access to both a private beach and pool. There are so many things to do in the area and the restaurants are fabulous. My family will definitely be back.
Quick stats about holiday rentals that are kid-friendly in Islamorada
Total rentals
60 properties
Nightly prices starting at
£60 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
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- Everglades National Park
- Sombrero Beach
- Zoo Miami
- John Pennekamp Coral Reef State Park
- Bahia Honda State Park
- Biscayne National Park
- Cannon Beach
- Long Beach
- Sandspur Beach
- Coral Castle
- Monkey Jungle
- Cocoa Plum Beach
- Windley Key Fossil Reef Geological State Park
- EAA Air Museum
- Calusa Beach & Loggerhead Beach
- Theater of the Sea
- Far Beach
- Horseshoe Beach
- Keys' Meads
- Everglades Alligator Farm
- Long Key State Park
- Sea Oats Beach