Book Kid-Friendly Hotels in Islamorada from $304

Name: Bayside Villas by Islander Resort
Price range: $452 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! (162 reviews)

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

Travelers say...

The Caribbean resort was absolutely perfect in every way! The property is so charming with nice amenities and a beautiful view of the water. Our house/cottage was immaculate and cozy! We loved this place and will be back!

Reviewed on Jan 23, 2026

Get rates

Islander Resort

82100 Overseas Highway Islamorada FL

Fully refundableReserve now, pay when you stay

$419 total

per night

Feb 5 - Feb 6

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! (1,012 reviews)

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

Travelers say...

This place is great. A must stay. Everyone is so friendly. Place is spotless clean

Reviewed on Jan 22, 2026

Cheeca Lodge & Spa

81801 Overseas Highway, Mile Marker 82 Islamorada FL

Fully refundableReserve now, pay when you stay

$383 total

per night

Feb 4 - Feb 5

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! (1,301 reviews)

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

Travelers say...

This palce is awesome. Clean rooms. 2 large pools with a view. Covered garage spot.

Reviewed on Jan 22, 2026

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

84001 Overseas Hwy Islamorada FL

Fully refundableReserve now, pay when you stay

$400 total

per night

Feb 4 - Feb 5

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! (134 reviews)

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

Travelers say...

Great place

Reviewed on Jan 22, 2026

Amara Cay Resort

80001 Overseas Hwy Islamorada FL

Fully refundableReserve now, pay when you stay

$345 total

per night

Feb 1 - Feb 2

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! (1,272 reviews)

No issues

Reviewed on Jan 20, 2026

Bayside Villas by Islander Resort

81450 Overseas Highway Islamorada FL

Fully refundableReserve now, pay when you stay

$452 total

per night

Feb 4 - Feb 5

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! (406 reviews)

Staff was very responsive. Great location

Reviewed on Jan 25, 2026

La Siesta Resort & Villas

80241 Overseas Highway Islamorada FL

Fully refundableReserve now, pay when you stay

$312 total

per night

Feb 4 - Feb 5

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! (1,003 reviews)

We stayed in one of the bungalows and absolutely loved it! It was awesome to walk right out of your room onto the beach. We really enjoyed the kayaking.

Reviewed on Jan 23, 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.

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

Get rates

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

$419 total

per night

Feb 5 - Feb 6

9.2/10 Wonderful! (1,012 reviews)

Hotels with Childcare in Islamorada

Cheeca Lodge & Spa

81801 Overseas Highway, Mile Marker 82 Islamorada FL

$383 total

per night

Feb 4 - Feb 5

9.2/10 Wonderful! (1,301 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!