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 S$134 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
Stay at this 4-star luxury 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! (1,007 reviews)

Families like: Outdoor pools, children's club, playground, games room

Travellers say...
"Had an amazing and relaxed time with my family! Dolphin encounter was so much fun and educational. I do recommend having a microwave in rooms. Thank you for the amazing hospitality 🙏"

Reviewed on 15 Sept, 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! (2,777 reviews)
"Our concierge was amazing! Very attentive and accommodating."

Reviewed on 25 Sept, 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! (1,022 reviews)

Families like: Outdoor pools, mini golf, on the beach, bike rentals

Travellers say...
"Stunning resort with great amenities and excellent service!"

Reviewed on 28 Sept, 2025

Islander Resort
See all 8,398 properties in Florida Keys
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. Book Flight + Lodging, save up to 100% of flight price - Savings based on flight + lodging package prices as compared to the price of the same components available for booking separately before all discounts and rewards applied. Your bundled savings cover up to 100% of your flight. Savings vary based on origin/destination, length of trip, stay dates and travel suppliers. Savings not available on all flight + lodging package bookings.