
Windley Key Holidays
- Plan, book, travel with confidence
Better together
Save up to S$134 when you book a flight and hotel together*
Find the right fit
With over 300,000 hotels worldwide, it's easy to create a perfect package
Rest easy
Plan, book, and manage your trip all in one place
Top hotels in Windley Key

Three Waters Resort and Marina, Islamorada, a Tribute Portfolio Resort
84001 Overseas Hwy, Islamorada, FL
Fully refundableReserve now, pay when you stay
The price is S$354 per night from 9 Sept to 10 Sept
S$354
9 Sept - 10 Sept
includes taxes & fees
9/10 Wonderful! (65 reviews)
"We were only there a couple of days but we had a great time! It's typical Key West layed back vibe!"
Reviewed on 26 Aug, 2025

Fisher Inn Resort & Marina
84951 Overseas Hwy, Islamorada, FL
Fully refundable
The price is S$184 per night from 14 Sept to 15 Sept
S$184
14 Sept - 15 Sept
includes taxes & fees
8/10 Very Good! (1,000 reviews)
"Great views manatees cruising by very relaxing"
Reviewed on 23 Aug, 2025

Coconut Cove Resort and Marina
84801 Overseas Highway, Islamorada, FL
The price is S$166 per night from 28 Aug to 29 Aug
S$166
28 Aug - 29 Aug
includes taxes & fees
7.6/10 Good! (815 reviews)
"Staff were very nice and welcoming. Nice pool and view. Room was nice clean and comfortable. Definitely would stay again"
Reviewed on 15 Aug, 2025
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.
What to do in Windley Key

Mangroves and Manatees - Guided Kayak Eco Tour
S$86
per adult
96% of travellers recommend

Original Snorkel and Sandbar Combo in Islamorada
S$192
per adult
90% of travellers recommend

1.5 Hour (20 miles) Waverunner Tour. See Mangrove Tunnels, 20 Islands & SandBar
S$333
per adult
100% of travellers recommend
Frequently asked questions
More trip options
Expedia's Latest Trends
Hotels
- Ko Lanta hotels
- Oriental Hotel Kyoto Rokujo
- Tui Magic Life Penelope Beach
- Fairmont Makati
- Colmar Tropicale
- Hotel Sapa Square, Affiliated by Meliá
- Bangkok City Hotel
- Hotels with smoking rooms in Milan
- Family friendly Hotels in Penang
- The Landmark Penthouse Luxury Condo by Casa Accommodation
- Resorts Yogyakarta
- Harmoni Suites Hotel
Flights
Activities
Packages
* 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.