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Top Family Resorts in the Florida Keys

At TravelingMamas.com we love to travel the globe searching for the best family friendly destinations, romantic escapes, and places for those girlfriend getaways. One destination that offers all three is The Florida Keys. Here are a few of the family friendly lodging choices we found for our readers.

The beach at Cheeca Lodge by Shannon Hurst Lane
The beach at Cheeca Lodge by Shannon Hurst Lane

Cheeca Lodge, Islamorada – Little CajunMama and I checked out this place on a mother-daughter trip. You can read about our experience at this family friendly resort and LCMs take on Camp Cheeca. We also made a video/slideshow of our stay.

Tranquility Bay Beach House Resort – I checked this place out solo to see if it met with our Traveling Mamas standards. The beach is definitely family friendly for even the littlest ones. These townhouse-style beach houses are perfect for families wanting to stay in one spot for their vacation. Each unit offers a kitchen, eliminating the need to leave the property during your stay. However, if cooking isn’t on your agenda, the beach bar and property restaurant is convenient and offers a wide variety on their menu. Two pools, one for families and an adult-only pool, is smart for a property to offer. I personally enjoyed the balcony of my oceanview unit and looked forward to evenings sipping wine and looking at the stars.

CajunMama finding Nirvana at Tranquility Bay Resort
CajunMama finding Nirvana at Tranquility Bay Resort
Sunset Key Island by Shannon Hurst Lane
Sunset Key Island by Shannon Hurst Lane

Sunset Key Island – This 27-acre luxury resort property has residential and resort units. One site is private, for residents. The other side offers the cutest little beach bungalows, some beachfront and others on the interior of island. If I was kid again, I would love spending a few days here playing in the sand. This property is a little pricey due to the location and atmosphere. There are tennis courts and other recreational opportunities on this getaway island, and during school holidays, group activities for kids are scheduled. The onsite gift shop is very pricey (Flipflops $50) but Latitudes Beach Cafe (onsite restaurant) offered some of the best French Toast I’ve ever eaten. Visitors are transported to and from the island from the dock at the Westin Key West Resort.

Stuffed French Toast at Latitudes Beach Cafe on Sunset Key Island
Stuffed French Toast at Latitudes Beach Cafe on Sunset Key Island

The Florida Keys offers a variety of attractions and activities for families. There are so many places to see and so many things to do that you just might have to plan multiple visits. Be sure to check out our Top 10 Family Activities in Key West.

Note: Key West and the Florida Keys are luxury family destinations and not inexpensive. While there may be some cheaper lodging choices in the Florida Keys area, they may not be family-friendly..

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  1. I second your vote for Cheeca Lodge! We’ve stayed there several times (with and without kids) and it’s a very family-friendly resort. My kids love the Keys because there’s so much for them to do on, near and under the water.

    There’s a kayak outfitter right in Islamorada that offers great guided kayak tours into the mangroves (Back Country Cowboy). We’ve gone on snorkeling trips from Bud ‘n Mary’s Marina. And the kids love to feed the tarpon (and watch for manatees) at Robbie’s. Plus, if you have a car, drive a little further south and do a dolphin swim at Hawk’s Cay Resort.

  2. Yiks! Who can spend that kind of money just for the hotel on a family vacation. Anyone can find a nice place for $1000 a night. The challenge is finding one for $300 a night.

  3. Are you kidding? …. Even under construction Sunset Key is 800 a night. Which family do you have in mind here? These are not recommendations with wide appeal because of the cost alone! Nice luxury choices, but where are the family choices during a recession!?!

  4. Hawks Cay Resort was very fun and kid oriented. I found the caged dolphines to be depressing. The dolphines are treated well and in a natural ocean pool, however it’s still a sad sight and makes you feel powerless.

  5. All of these wonderful, luxurious places sound great, but I’m unsure of where to take my 1st family vacation. Where could I possibly bring my 2 yr-old daughter so that we can both have lots of fun in the sun? Someone please help!!!

  6. no way are these reasonable family choices based on cost. Cheapest room rate i could find was $550 a night. Sorry im not spending $4000 on just the room rate. Not helpful here.

  7. The Florida Keys isn’t a budget destination and is popular not just for families but for all demographics of travelers. Kevin’s comment concerned me, regarding overall cost. Keep in mind that Sunset Key is a somewhat private island and you are paying for the exclusivity. Cheeca Lodge can be expensive, but I was able to find a room for $219 based on the dates Sept 20-25. I did the same search for Tranquility Bay and was able to find a 2 bedroom beach house for $159 per night. As with any hotel or destination, you pay more for views and peak travel dates. Sunset Key was $665 for a one bedroom cottage based on the same seach dates.

  8. Hi Shannon,
    great post. Which did you like better tranquility bay or cheeca lodge? we will be bringing our 2 kids ages 9 and 6.
    we r thinking of tranquility bay since the price is lower. Is there a lot to do in marathon? I keep hearing islamarodo is more happening.

  9. Hi Shannon – Great post, but I think you’re missing a major one: Hawks Cay! It’s on Duck Key, not far from Marathon. My husband and I just returned from a romance trip there, but I could definitely tell it was a great family destination resort. Their kid-oriented Indies Club has daily activities for kids and places for them to hang out, such as pool tables, a pirate ship pool and more. We also took part in the Dolphin Connection experience at the on-site dolphin training facility, where we got to spend about half an hour in the water with the dolphins. Most of their dolphins are retired from other facilities and are treated very nicely. It was great fun!

  10. Hi Shannon,
    I love this article, what a great resource for first time parents on the road with their kids! Thanks so much for sharing, can’t wait to read more and plan a trip with my family to the Florida Keys!

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