Book Kid-Friendly Hotels in Islamorada from $137

Name: Bayside Villas by Islander Resort
Price range: $352 total
Rating: 8.8

Find & compare hotels, resorts and vacation rentals for the whole family

Top Islamorada Kid Friendly Hotels

The Caribbean Resort

117 Carroll St Islamorada FL

A marina and an outdoor pool are featured at this hotel. There's a hot tub on site, and a terrace and a garden are also provided.

9.8/10 Exceptional! (159 reviews)

Families like: Outdoor pool, kitchen, bicycle rentals, washer and dryer

Travelers say...

We thoroughly enjoyed our stay! The property is clean, peaceful, and welcoming. We plan to return.

Reviewed on Dec 11, 2025

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Islander Resort

82100 Overseas Highway Islamorada FL

Fully refundableReserve now, pay when you stay

$325 nightly

$366 total

Dec 18 - Dec 19

Total with taxes and fees

A private beach, 3 restaurants, and 2 outdoor pools are all featured at this hotel. Enjoy beachfront dining and relax with beach cabanas and sun loungers. Families ...

9.2/10 Wonderful! (1,002 reviews)

Families like: Outdoor pools, miniature golf, on the beach, bicycle rentals

Travelers say...

This resort was just what we needed. It started out with a small hicup, we checked in late and they gave our king bed room away. Front desk said something like Expedia oversells their property and there was nothing left that she could do. We had to take the double room. After a while my husband went ...

Reviewed on Dec 8, 2025

Cheeca Lodge & Spa

81801 Overseas Highway, Mile Marker 82 Islamorada FL

Fully refundableReserve now, pay when you stay

$241 nightly

$272 total

Dec 16 - Dec 17

Total with taxes and fees

This luxury resort features a private beach, a golf course, and a full-service spa. Enjoy beachfront dining and relax with sun loungers and beach umbrellas. ...

9.2/10 Wonderful! (1,268 reviews)

Families like: Outdoor pools, kids club, playground, game room

Travelers say...

Everything was awsome

Reviewed on Dec 7, 2025

Three Waters Resort and Marina, Islamorada, a Tribute Portfolio Resort

84001 Overseas Hwy Islamorada FL

Fully refundableReserve now, pay when you stay

$278 nightly

$313 total

Dec 17 - Dec 18

Total with taxes and fees

This Art Deco resort features a private beach, a marina, and 4 restaurants. Enjoy a day at the beach snorkeling, or relax with sun loungers. Families will appreciate ...

9/10 Wonderful! (114 reviews)

Families like: Outdoor pools, game room, on the beach, bicycle rentals

Travelers say...

Beautiful room, stunning views

Reviewed on Nov 19, 2025

Amara Cay Resort

80001 Overseas Hwy Islamorada FL

Fully refundableReserve now, pay when you stay

$226 nightly

$255 total

Dec 18 - Dec 19

Total with taxes and fees

A private beach and a restaurant are featured at this resort. If you want to take your pet along, this pet-friendly property offers everything you'll need for ...

8.8/10 Excellent! (1,260 reviews)

very nice staff, quiet and comfortable

Reviewed on Dec 10, 2025

Bayside Villas by Islander Resort

81450 Overseas Highway Islamorada FL

Fully refundableReserve now, pay when you stay

$312 nightly

$352 total

Dec 18 - Dec 19

Total with taxes and fees

This hotel features 3 restaurants, a bar/lounge, and an outdoor pool. There's no skimping on freebies - guests receive free WiFi, free self parking, and a free ...

8.8/10 Excellent! (399 reviews)

I loved the property, the staff and all the amenities.

Reviewed on Nov 30, 2025

La Siesta Resort & Villas

80241 Overseas Highway Islamorada FL

Fully refundableReserve now, pay when you stay

$212 nightly

$239 total

Dec 18 - Dec 19

Total with taxes and fees

The private beach and marina are among the highlights at this resort. Enjoy the outdoor pool and perks like a free area shuttle. There's a poolside bar on site, ...

8.6/10 Excellent! (1,001 reviews)

Great stay and beautiful space

Reviewed on Dec 1, 2025

Conch On Inn Motel

103 Caloosa Street Tavernier FL

This motel doesn't skimp on freebies - guests receive free WiFi and free self parking. A garden, concierge services, and barbecue grills are also on offer.

The room was about 90° when we got there and never did cool off for two days we were there. Water pressure in the bathroom was bad. And one of the owners gave us a real bad attitude when we inquired about checking out a little bit late on our last day. We will never go back there again I would not ...

Reviewed on Aug 6, 2018

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Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

Hotels With Pools in Islamorada

Islander Resort

82100 Overseas Highway Islamorada FL

$325 nightly

$366 total

Dec 18 - Dec 19

Total with taxes and fees

9.2/10 Wonderful! (1,002 reviews)

Hotels with Childcare in Islamorada

Cheeca Lodge & Spa

81801 Overseas Highway, Mile Marker 82 Islamorada FL

$241 nightly

$272 total

Dec 16 - Dec 17

Total with taxes and fees

9.2/10 Wonderful! (1,268 reviews)

Islamorada Kid-Friendly Hotels

It’s not a family vacation if you can’t bring the entire clan with you, is it? Next time you have a few days off from work, plan a family-friendly getaway. Set off on an adventure the entire family will love, and book your stay at one of the kid-friendly hotels in Islamorada.

Your little ones are the most important thing in your life, so make sure they enjoy your accommodation as much as you do. From a kids-only room service menu (macaroni and cheese, anyone?) to special perks like in-room video game consoles, these lodgings provide a little something extra for the smaller members of your crew. The best family-friendly hotels in Islamorada may even offer playgrounds and other activities to keep the kiddos busy. What’s more, some hotels provide a babysitting service so you can get a few hours to yourself!

Whether you’re traveling with one small child or hauling around your entire extended family, Travelocity is here to help. Let us hook you up with hotels for kids in Islamorada that will keep your youngsters happy without breaking the bank. You can save even more when you bundle your flight and hotel together, so what are you waiting for? Grab your family and get ready to explore!

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Recent Islamorada Hotel Reviews By Fellow Wanderers

Chesapeake Beach Resort

5 out of 5

Posted 2 days ago

Travelocity Verified Review

"Wonderful place!"

A verified traveler stayed at Chesapeake Beach Resort

Islander Resort

5 out of 5

Posted 6 days ago

Travelocity Verified Review

"This resort was just what we needed. It started out with a small hicup, we checked in late and they gave our king bed room away. Front desk said something like Expedia oversells their property and there was nothing left that she could do. We had to take the double room. After a while my husband went on their website and found availability for a king bed, he showed the front desk and wow all of a sudden they had a king for us! The resort was very relaxing, with an all inclusive Caribbean vibe minus the pushy water aerobics instructor trying to get you to participate lol! The food was good at the poolside bar and there was always staff walking around to take orders for drinks. The rooms were really nice, clean and modern. The only negative was the vanity was really small with no room for toiletries. I had to carry everything in the bathroom with me when I was getting ready or washing my face at night. I’m not sure if it was the time of year or what but the resort was not busy at all and felt very quiet and relaxing. You never had to fight for beach chairs or pool chairs. Lots of great restaurants a short drive away too."

A verified traveler stayed at Islander Resort