Florida Keys Kid friendly Holidays

Book a Hotel + Flight or Car together to unlock savings

  • Plan, book, travel with confidence

  • payments icon

    Better together

    Save up to P 3,118 when you book a flight and hotel together*
    lob hotels icon

    Find the right fit

    With over 300,000 hotels worldwide, it's easy to create a perfect package
    lob packages icon

    Rest easy

    Plan, book, and manage your trip all in one place
Hawks Cay Resort

Hawks Cay Resort

4 out of 5
61 Hawks Cay Blvd, Marathon, FL
  • 2 hours drive from Duval Street
Book a stay at this beach hotel in Marathon. Enjoy free WiFi, 5 outdoor pools, and a full-service spa. Our guests praise the pool and the helpful staff in our ...
8/10 Very Good! (1,003 reviews)
"So fun. Loved my room and having Dolphin Connection right there for my kids. Food at all the restaurants from poolside to fancy was delicious."

Reviewed on Aug 10, 2025

Hawks Cay Resort
Southernmost Beach Resort and Guesthouses

Southernmost Beach Resort and Guesthouses

4 out of 5
1319 Duval Street, Key West, FL
  • 11 min walk from Duval Street
Stay at this 4-star beach hotel in Key West. Enjoy free WiFi, 3 outdoor pools, and a full-service spa. Our guests praise the pool and the bar in our reviews. ...
8.6/10 Excellent! (2,678 reviews)
"The place was amazing. The bellman were absolutely awesome 10/10, so friendly and helpful. Be sure to ask them for a taxi to the airport when you leave!! Same price if not cheaper than an uber, and great service."

Reviewed on Aug 16, 2025

Southernmost Beach Resort and Guesthouses
Islander Resort

Islander Resort

4 out of 5
82100 Overseas Highway, Islamorada, FL
  • 3 hours drive from Duval Street
Stay at this 4-star beach hotel in Islamorada. Enjoy free WiFi, free parking, and 2 outdoor pools. Our guests praise the pool and the helpful staff in our reviews. ...
9/10 Wonderful! (1,001 reviews)
"There was a lot of confusion with times and availability of amenities. We were given three different times for us of paddle boards and golfing. There was trash floating in the water had plastic wrap around my foot while kayaking. They were cleaning things up when we left so probably a one off. The ..."

Reviewed on Aug 16, 2025

Islander Resort
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.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.