Book Hotels in Windley Key, FL

Start date: Check-in selected.
To Date
End date: Check-out

Cabins, apartments, houseboats! We offer comfortable & private vacation rentals

Save an extra 10% or more on select hotels with Member Discounts

Access exclusive hotel deals, only with the Travelocity app

Check prices for these dates

Tonight
Jan 16 - Jan 17
Tomorrow
Jan 17 - Jan 18
This weekend
Jan 16 - Jan 18
Next weekend
Jan 23 - Jan 25

Filter by

Guest rating
Guest rating
Star rating
Payment type
Payment type
Property type
Property type
Neighborhood
Neighborhood
Traveler experience
Traveler experience
Popular locations
Popular locations
Meal plans available
Meal plans available
Amenities
Amenities
Accessibility
Accessibility

Top Windley Key hotels

Chesapeake Beach Resort

Chesapeake Beach Resort

3.5 out of 5
83409 Overseas Hwy Islamorada FL
Fully refundableReserve now, pay when you stay
$223 nightly
The price is $251 total per night from Jan 25 to Jan 26
$251 total
Jan 25 - Jan 26
Total with taxes and fees
A private beach, a marina, and 2 outdoor pools are all featured at this smoke-free hotel. Enjoy a day at the beach kayaking, or relax with sun loungers. Unwind ...
Very clean and nice. Not a 5 star resort. But nice. Breakfast was good

Reviewed on Jan 11, 2026

Opens in a new windowChesapeake Beach Resort
Lime Tree Bay Resort

Lime Tree Bay Resort

3.5 out of 5
68500 Overseas Hwy Long Key FL
$219 nightly
The price is $246 total per night from Jan 21 to Jan 22
$246 total
Jan 21 - Jan 22
Total with taxes and fees
This resort features a private beach, 3 outdoor pools, and a restaurant. Business travelers can take advantage of the free WiFi in public areas. Enjoy the outdoor ...
Beautiful resort on the beach and everything was perfect .

Reviewed on Jan 13, 2026

Opens in a new windowLime Tree Bay Resort
Cheeca Lodge & Spa

Cheeca Lodge & Spa

5 out of 5
81801 Overseas Highway, Mile Marker 82 Islamorada FL
Fully refundableReserve now, pay when you stay
$346 nightly
The price is $390 total per night from Jan 21 to Jan 22
$390 total
Jan 21 - Jan 22
Total with taxes and fees
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. ...
Overall our stay was fabulous. Some small gripes are the shower heads were built up with mineral deposits and didn’t spray properly and there was a leak in our ceiling above the toilet. However it is a beautiful resort. Lots of amenities, fun for the whole family

Reviewed on Jan 11, 2026

Opens in a new windowCheeca Lodge & Spa
Coconut Cove Resort and Marina

Coconut Cove Resort and Marina

3 out of 5
84801 Overseas Highway Islamorada FL
$249 nightly
The price is $280 total per night from Jan 19 to Jan 20
$280 total
Jan 19 - Jan 20
Total with taxes and fees
A marina and an outdoor pool are featured at this hotel. Families will appreciate the children's pool and barbecue grills. Enjoy the gym and free perks like ...
Would stay again

Reviewed on Jan 13, 2026

Opens in a new windowCoconut Cove Resort and Marina
Three Waters Resort and Marina, Islamorada, a Tribute Portfolio Resort

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

3.5 out of 5
84001 Overseas Hwy Islamorada FL
Fully refundableReserve now, pay when you stay
$347 nightly
The price is $391 total per night from Jan 21 to Jan 22
$391 total
Jan 21 - Jan 22
Total with taxes and fees
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 ...
We had a wonderfull time. Everyone was very attentive and helpful.

Reviewed on Jan 11, 2026

Opens in a new windowThree Waters Resort and Marina, Islamorada, a Tribute Portfolio Resort
Waterside Suites & Marina

Waterside Suites & Marina

3.5 out of 5
201 Ocean Drive Key Largo FL
Fully refundableReserve now, pay when you stay
$159 nightly
The price is $179 total per night from Jan 25 to Jan 26
$179 total
Jan 25 - Jan 26
Total with taxes and fees
A marina and an outdoor pool are featured at this smoke-free hotel. WiFi in public areas is free. A terrace, a picnic area, and luggage storage are also on ...
Floors greasy

Reviewed on Jan 13, 2026

Opens in a new windowWaterside Suites & Marina
Drop Anchor

Drop Anchor

3 out of 5
84959 Overseas Highway, 222 Islamorada FL
$192 nightly
The price is $212 total per night from Jan 19 to Jan 20
$212 total
Jan 19 - Jan 20
Total with taxes and fees
An outdoor pool, free self parking, and barbecue grills are featured at this hotel. WiFi in public areas is free. A business center, a garden, and a picnic area ...
Great

Reviewed on Jan 14, 2026

Opens in a new windowDrop Anchor
Marina Del Mar Resort and Marina

Marina Del Mar Resort and Marina

2.5 out of 5
527 Caribbean Drive Key Largo FL
Fully refundableReserve now, pay when you stay
$157 nightly
The price is $177 total per night from Jan 25 to Jan 26
$177 total
Jan 25 - Jan 26
Total with taxes and fees
A marina, 2 restaurants, and an outdoor pool are all featured at this smoke-free hotel. Enjoy the gym and perks like free self parking and free WiFi. You'll ...
Our room was huge and Clean. We arrived early and our room was ready. Saw a manatee in the Marina as well as a nurse shark. Plenty of pelicans to watch and great food and entertainment on the premises.

Reviewed on Jan 12, 2026

Opens in a new windowMarina Del Mar Resort and Marina
Fisher Inn Resort & Marina

Fisher Inn Resort & Marina

3.5 out of 5
84951 Overseas Hwy Islamorada FL
Fully refundable
$200 nightly
The price is $225 total per night from Jan 19 to Jan 20
$225 total
Jan 19 - Jan 20
Total with taxes and fees
A private beach and an outdoor pool are featured at this Art Deco motel. Spend a day at the beach snorkeling, or relax with sun loungers and beach umbrellas. ...
This place is a very cute little stay. Easy in and out and convenient parking. Breakfast was good with your basic continental items. The shower had no water pressure but we managed. Bring your own shampoo and conditioner and soap. Room and bathroom was very clean. The beach section is great but could ...

Reviewed on Jan 10, 2026

Opens in a new windowFisher Inn Resort & Marina
Don't see what you're looking for?
See all available properties in Windley Key
View all properties
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.

Recent Windley Key hotel reviews by fellow wanderers

Drop Anchor

Drop Anchor

5 out of 5
Posted 2 days ago
Travelocity Verified Review
"Great"
A verified traveler stayed at Drop Anchor
Drop Anchor

Explore More Ways to Travel with Travelocity