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Kid-friendly holiday rentals in Islamorada

Find and book unique family-friendly rentals on Airbnb

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Popular amenities for Islamorada family-friendly rentals

Kid-friendly house rentals

Superhost
Home in Goulds
4.81 out of 5 average rating, 21 reviews

Stylist House 5bed

TaComyRating, 5 stars2 weeks ago
The property was beautiful just as photographed. The neighborhood was quiet and peaceful.
Top guest favourite
Home in Marathon
5 out of 5 average rating, 12 reviews

Waterfront Oasis w/Private Pool-Dockage-Beach

DaveRating, 5 stars3 months ago
Incredible property. Perfect gathering space for my entire family of 6. Private yet close to commerce like Publix and local gym to work out. Great memories made.
Guest favourite
Home in Key Colony Beach
4.94 out of 5 average rating, 108 reviews

Waterfront Home 37.5-ft dock, Cabana Club Included

AllisonRating, 5 stars2 weeks ago
The house was just as described. Loved having meals on the screened in porch each morning while watching the boats and wildlife float/fly by. Very peaceful setting. Modern bathrooms and kitchen. Also the Cabana Club pool and beach was a wonderful place to relax. We enjoyed meeting other Key Colony residents/visitors at the pool and at Sunset Park. They have concerts on Sunday afternoons in the park.
Top guest favourite
Home in Key Largo
4.95 out of 5 average rating, 20 reviews

Island Breeze

JenniferRating, 5 stars1 week ago
We loved the private pool and tiki bar. The outdoor refrigerators were perfect to spend the day at the pool. The house was very clean with a perfect set up for our 2 families. We would definitely stay here again!
Superhost
Home in Naranja
4.88 out of 5 average rating, 72 reviews

Resort Style Pool House Mini-Golf Game-Room Casino

LisaRating, 5 stars1 day ago
This home was super clean and just as described. The pool, outdoor area, and game room were all pretty awesome. Our family enjoyed the use of all the home had to offer.
Superhost
Home in Key Colony Beach
4.73 out of 5 average rating, 133 reviews

NEW PET FRIENDLY Waterfront Single Home-Pool,Beach

CherylRating, 5 stars3 months ago
Mary's place was in a very safe and beautiful location. Everyone was friendly and there were endless dining options. There were even local conveniences that I didn't expect nearby such as Dollar Tree, Winn Dixie, Home Depot, etc. Showers had great water pressure, hot water, and had zero sulphur smell. Decor was lovely and ample storage space for your things. A/C and heat works great and no musty smells anywhere. Beds, outdoor furniture and couches very comfortable. Convenient off-street parking. Was too busy to enjoy the cabana amenities but visited it briefly and it looked wonderful. Thank you Mary hope to return in the future!
Guest favourite
Home in Homestead
4.92 out of 5 average rating, 183 reviews

Quaint Spanish Colonial House

MelissaRating, 5 stars5 days ago
We're so glad we decided to stay here and would love to come back again! 3 nights here were not long enough - the house is perfect for a family and there's so much to do in the area! Vilma was so welcoming when we arrived and she is the perfect host! The house had everything we needed (and more!) for our stay, and Vilma and Erasmo were quick to help whenever we had questions and to provide lots of recommendations of sights to see and places to eat. The beds are comfy, showers were hot and with good water pressure, and we really appreciated the extra special touches of things like muffins for our first breakfast there, coffee and creamers, water bottles, beach towels, baby crib and highchair, and even a cooler box for our day trips. Homestead was the perfect base for trips to Miami, the Florida Keys and the Everglades. We would highly recommend this house for both big and small groups alike. Thanks for a great stay Vilma and Erasmo!
Superhost
Home in Summerland Key
5 out of 5 average rating, 10 reviews

Pelico Palm Villa

KellyRating, 5 stars12 months ago
This home was absolutely beautiful!! It was exactly what we had hoped for, We were a family of 4 with my husband and I, with are two sons, ages 17 & 20, plus ones girlfriend age 16. We wanted a nice family vacation without the spring break chaos & this was it! This home was so clean yet cozy, had all the necessities we needed, everyone had their own room and bathroom which was super!!! This home could definitely accomodate so many more if you wanted to do so. We were the only ones there at the time, so we had the pool area to ourselves which we loved sooooo much! We played bags by the pool daily, swam during day & at night. The home had a great deck with a wonderful grill, we made slushy drinks with the ninja blender, anything you wanted this place had! We traveled to Key West a couple times which was nice and close, about a 30 minute drive. All in all this place is top notch! Don't hesitate to book! It's worth it!! LOVED this Home!! & Nate was a spectacular host!!!

Family-friendly apartment rentals

Superhost
Flat in Cutler Bay
4.67 out of 5 average rating, 3 reviews

Delightful Apartment Miami: 1BR / BBQ & Kitchen

AlceonRating, 5 stars1 month ago
Apartment Style accommodation. This space beautifully decorated. The attention to detail was a welcome surprise. Little things like seasoning in the cupboard if you wanted to make a meal or a spear tooth brush if you forgot yours. Felt like home away from home. Thank you for making my experience special.
Top guest favourite
Flat in Key Largo
4.99 out of 5 average rating, 142 reviews

Kawama Lagoon, 3D corner chickee 2bdr , 2 baths

EowynRating, 5 stars3 months ago
A lovely and unique stay in Key Largo! The listing was better than the photos, I love the ocean theme and all of the color. I particularly appreciated having access to kayaks. The hosts are also lovely and provided help as needed and recommendations. I would love to return.
Guest favourite
Flat in Princeton
4.88 out of 5 average rating, 186 reviews

Retreat entire apartment (not shared)

JocelynRating, 5 stars3 days ago
beautiful and cozy place! highly recommend staying at this wonderful place. my friend and I stayed here for a week and it perfectly fit our needs. Claudia was very flexible with our late check in and quickly responsive! i would give 10 stars if i could ⭐
Top guest favourite
Flat in Homestead
5 out of 5 average rating, 8 reviews

Charming 1 Bedroom Apartment

EtienneRating, 5 stars6 days ago
Look no further, I highly recommend this place!! Jennifer is an exemplary host with attention to detail and the well-being of guests at heart. The place was very clean, inviting, well arranged and very private. The instructions were very clear and well established. The location is perfect and close to all shops in addition to being about halfway between the Keys and Miami. Thanks Jennifer:)
Superhost
Flat in Key Largo
4.92 out of 5 average rating, 261 reviews

Waterfront Studio 2| Couples Oasis | Kayaks | Pool

KarenRating, 5 stars2 weeks ago
We enjoyed our stay. The place was very clean and exactly as pictured. I will say it was a bit small for four people though. Not really anything with walking distance so you definitely need a car. The use of the kayaks and paddleboards were a definite plus!
Superhost
Flat in Big Pine Key
4.78 out of 5 average rating, 37 reviews

Apartment in Big Pine

EvanRating, 5 stars2 weeks ago
This place was a great stay. The room has everything you need and the hosts are amazing.I believe a family lives below but if there wasn’t a car in the driveway we wouldn’t have even noticed. The place is super clean and very well taken care of. Had everything you need. You’re about 45 min from key west as well! We had a great time and a good stay. Would recommend for anyone trying to have a good vacation!
Superhost
Flat in Key Largo
4.83 out of 5 average rating, 336 reviews

Escape to the Keys!

SJRating, 5 stars3 weeks ago
Ana’s place was beautiful and a delight to stay at. It was in a very convenient spot which allowed us to make pit stops at the house in between trips up and down the keys. Ana was a great host, and I would definitely recommend staying here.
Guest favourite
Flat in Marathon
4.97 out of 5 average rating, 102 reviews

Beachfront Condo w/ Ocean Views in Marathon

WendyRating, 5 stars2 months ago
Stunning views, peaceful. we had stayed in this building before 7 years ago and found other vacations have never measured up to the view. This owner puts money back into his investment, furniture was comfortable, kitchen was beautiful and well stocked. This is a end unit so you really get special views! We definitely are going home with huge smile on our faces and are so distressed. On top of all that the unit was so clean!❀

Family-friendly apartment rentals

Superhost
Apartment in Key Colony Beach
4.86 out of 5 average rating, 180 reviews

2 Bedroom Oceanfront Complex, Key Colony Beach

SarahRating, 5 stars1 month ago
We just returned from our stay in Key Colony and it was everything we had dreamed of. It was a wonderful location, right in between flying into Ft. Lauderdale, and traveling one day into Key West. The property overall was very well maintained, beautiful and private. The beach area was perfect and gave us a lovely day of relaxation enjoying the views and all the sounds. Our condo itself was just as described and had the perfect amenities needed to spend a few days and celebrate my husband's birthday. Kim is a fantastic host! She is very responsive and provided lots of information about all things in and around the condo.
Superhost
Apartment in Tavernier
4.89 out of 5 average rating, 157 reviews

2BR - Key Largo Sunshine Getaway

NoelleRating, 5 stars1 week ago
Adorable condo! Great location and the private beach area was perfect. Vanessa was a wonderful host!
Guest favourite
Apartment in Key Largo
5 out of 5 average rating, 14 reviews

Key Lime Breeze Ocean Retreat | Waterfront Oasis

TaraRating, 5 stars1 week ago
The host were great and so proactive. They showed such great hospitality and provided a wonderful home to stay in. The apartment down stairs was so perfect for our parents. The kids loved the pools and pickle ball courts! Also, loved all the extras like the pool toys and having access to a washer and dryer. Thanks again for the wonderful stay!
Superhost
Apartment in Marathon
4.86 out of 5 average rating, 7 reviews

Duck Key Getaway: Charming 3BR Condo, Water Views

KimRating, 5 stars3 weeks ago
We wish we had more time to explore the community but our stay was very short. The place was lovely - just as described. The beds were comfortable. Everything was very clean. My daughter left a favorite shirt behind accidentally, and Tina was very responsive, assuring us the cleaning staff had found it, and would mail it back to us. We were quite pleased and very grateful. We would certainly stay here again.
Guest favourite
Apartment in Key Largo
4.9 out of 5 average rating, 77 reviews

Island Palms~Overlooking Tennis Courts

JenniferRating, 5 stars2 weeks ago
What a great condo! Felt right at home and has everything you need! Diane was very excellent with communication & details of what we would need. Would highly recommend staying here. Snappers restaurant is a great spot for lunch or dinner!
Superhost
Apartment in Key Largo
4.86 out of 5 average rating, 125 reviews

Waterfront Spacious Condo Key Largo #4, 10% Off 7+

AustinRating, 5 stars5 days ago
The first half of our stay went extremely well and there was plenty of space to park our boat. I would definitely stay again.
Guest favourite
Apartment in Tavernier
4.9 out of 5 average rating, 117 reviews

Luxurious Suite+Open Ocean Views+Pool & Cabana Bar

CarolineRating, 5 stars2 weeks ago
We very much enjoyed our stay. Largo was a very kind and helpful host. The ocean views are beautiful and we enjoyed the pool and the private beach. We would love to come back.
Guest favourite
Apartment in Key Largo
4.77 out of 5 average rating, 62 reviews

Spring-Summer Deals! LUX Oceanfront 1300sf Condo!

JeromeRating, 5 stars1 week ago
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.

Quick stats about holiday rentals that are kid-friendly in Islamorada

  • Total rentals

    60 properties

  • Nightly prices starting at

    ÂŁ62 before taxes and fees

  • Total number of reviews

    1K 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

  1. Airbnb
  2. United States
  3. Florida
  4. Monroe County
  5. Islamorada
  6. Family-friendly rentals