Book Kid-Friendly Hotels in Islamorada from $193

Name: Bayside Villas by Islander Resort
Price range: $315 total
Rating: 9

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.

10/10 Exceptional! (174 reviews)

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

Travelers say...

"This is brand new property tucked away in a private little alcove--- Has a great pool and a boat ramp and dock if you bring your boat. Very low key."

Reviewed on Jun 19, 2026

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Islander Resort

82100 Overseas Highway Islamorada FL

Fully refundableReserve now, pay when you stay

$260 nightly

$293 total

Aug 2 - Aug 3

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 ...

9.4/10 Exceptional! (1,078 reviews)

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

Travelers say...

"Great room, perfect breakfast"

Reviewed on Jul 10, 2026

Cheeca Lodge & Spa

81801 Overseas Highway, Mile Marker 82 Islamorada FL

Fully refundableReserve now, pay when you stay

$232 nightly

$261 total

Aug 11 - Aug 12

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! (1,346 reviews)

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

Travelers say...

"There were a lot of activities to do with the kids during summer break. They have 3 big pools. The property was Right on the ocean. The Staff was very nice."

Reviewed on Jul 10, 2026

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

84001 Overseas Hwy Islamorada FL

Fully refundableReserve now, pay when you stay

$319 nightly

$359 total

Aug 9 - Aug 10

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! (226 reviews)

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

Travelers say...

"T"

Reviewed on Jul 10, 2026

Bayside Villas by Islander Resort

81450 Overseas Highway Islamorada FL

Fully refundableReserve now, pay when you stay

$280 nightly

$315 total

Aug 11 - Aug 12

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 ...

9/10 Wonderful! (450 reviews)

"Nice place very clean , quiet . Was great stay for us , thank you"

Reviewed on Jul 4, 2026

Amara Cay Resort

80001 Overseas Hwy Islamorada FL

Fully refundableReserve now, pay when you stay

$232 nightly

$261 total

Jul 14 - Jul 15

Total with taxes and fees

A private beach, 2 restaurants, and an outdoor pool are all featured at this resort. If you want to take your pet along, this pet-friendly property offers everything ...

8.8/10 Excellent! (1,293 reviews)

"Highly recommend!"

Reviewed on Jul 10, 2026

La Siesta Resort & Villas

80241 Overseas Highway Islamorada FL

Fully refundableReserve now, pay when you stay

$259 nightly

$292 total

Aug 2 - Aug 3

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! (1,011 reviews)

"The room was very dirty when we arrived. The location and view from the room was amazing. The pool was great except it had black spots all over, which looked like black mold. There were also metal brush bristles from the staff cleaning the pool, on the bottom of the pool and a few people were cut ..."

Reviewed on Jul 9, 2026

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.

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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

$260 nightly

$293 total

Aug 2 - Aug 3

Total with taxes and fees

9.4/10 Exceptional! (1,078 reviews)

Hotels with Childcare in Islamorada

Cheeca Lodge & Spa

81801 Overseas Highway, Mile Marker 82 Islamorada FL

$232 nightly

$261 total

Aug 11 - Aug 12

Total with taxes and fees

9.2/10 Wonderful! (1,346 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!

Package deals, things to do & more in Islamorada

Recent Islamorada Hotel Reviews By Fellow Wanderers

Chesapeake Beach Resort

4 out of 5

Posted 6 hours ago

Travelocity Verified Review

"This was a nice place to get away from the urban Key West. The staff was very friendly and solved any issues regardless of the time (noisy neighbor, needed blanket) and the shore was close by. There was staff routinely monitoring the beach and property so it was very secure. The location has easy access to restaurants and shops if you have a car. The large pool had a bar / food and the property has a nice restaurant. The breakfast is cook to order pancakes and omelets, very nice! Pros Great staff everywhere! Ocean view is a real view if you select it We had a suite with a king bed and the teen had a separate fold out couch that was comfortable Microwave and mini-fridge were convenient Bathroom was very nice had a toilet in a separated section with a door A second pool was available with shade making it cooler in the summer Parking was easy and right outside, some covered by the buildings Elevator if you have the ocean view was very convenient Fresh omelet to order with a dozen ingredients, good yogurt options with toppings that were plentiful Balcony was very nice Reasonable price Cons - not much Next to a busy road. We could not hear it from outside the room door but there are two buildings and we were at the far building, so not bad at all for us Not much available without a car I recommend not going in June as the seaweed odor is unpleasant No one went to the beach but it was fine at the pool"

A verified traveler stayed at Chesapeake Beach Resort