Find hotels in Windley Key, FL from $155

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

  • Upfront pricing

    Our total price for your stay includes taxes and fees

  • Treat yourself

    Save 10% or more on over 100,000 hotels worldwide with Member Prices
    Learn about One Key

  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

Tonight
Dec 26 - Dec 27
Tomorrow
Dec 27 - Dec 28
This weekend
Dec 26 - Dec 28
Next weekend
Jan 2 - Jan 4

Filter by

Guest rating
Guest rating
Star rating

Our top choices for Windley Key hotels

Private beach, sun loungers, beach towels, scuba diving
Three Waters Resort and Marina, Islamorada, a Tribute Portfolio Resort

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

Three Waters Resort and Marina, Islamorada, a Tribute Portfolio Resort
4.0 star property
Islamorada
9.0 out of 10, Wonderful, (121)
"Beautiful chilled out hotel"
United Kingdom
Jacqueline
$356 nightly
The price is $400
Jan 4 - Jan 5, 2026
Total with taxes and fees
Three Waters Resort and Marina, Islamorada, a Tribute Portfolio Resort
Oceanfront King Suite w/ Kitchen & Private Balcony | Beach/ocean view
Drop Anchor

Drop Anchor

Drop Anchor
3.0 star property
Islamorada
8.8 out of 10, Excellent, (1003)
"Had a wonderful stay at Drop Anchor! Very adorable and super clean. Loved the amenities and the hotel staff were amazing! "
United States
Laura
$191 nightly
The price is $210
Jan 11 - Jan 12, 2026
Total with taxes and fees
Drop Anchor
Exterior
Fisher Inn Resort & Marina

Fisher Inn Resort & Marina

Fisher Inn Resort & Marina
3.5 star property
Islamorada
8.2 out of 10, Very Good, (1001)
"We enjoyed are stay at Fisher Inn, room was clean and updated. The paddle board use was a nice perk! "
United States
Magaly
$191 nightly
The price is $215
Jan 5 - Jan 6, 2026
Total with taxes and fees
Fisher Inn Resort & Marina
Exterior
Coconut Cove Resort and Marina

Coconut Cove Resort and Marina

Coconut Cove Resort and Marina
3.0 star property
Islamorada
9.0 out of 10, Wonderful, (157)
"Everything was great thank you"
United States
Ruth
$239 nightly
The price is $269
Jan 4 - Jan 5, 2026
Total with taxes and fees
Coconut Cove Resort and Marina
Classic Room, Patio, Garden View | Terrace/patio
The Ocean View Inn & Pub

The Ocean View Inn & Pub

The Ocean View Inn & Pub
2.0 star property
Islamorada
9.4 out of 10, Exceptional, (9)
"Awesome place to stay, restaurant and bar attached, outside bar and dining area overlooking the bay. Pool also very nice. "
United States
Rick
$177 nightly
The price is $199
Jan 8 - Jan 9, 2026
Total with taxes and fees
The Ocean View Inn & Pub
3 restaurants, breakfast, lunch, dinner served; American cuisine
Reefhouse Resort & Marina

Reefhouse Resort & Marina

Reefhouse Resort & Marina
3.5 star property
Key Largo
9.2 out of 10, Wonderful, (1327)
"Very relaxing with nice on-site activities. Bed can be better for better sleep"
United States
Jing
$309 nightly
The price is $343
Jan 4 - Jan 5, 2026
Total with taxes and fees
Reefhouse Resort & Marina
Outdoor pool, cabanas (surcharge), pool umbrellas
Playa Largo Resort & Spa, Autograph Collection

Playa Largo Resort & Spa, Autograph Collection

Playa Largo Resort & Spa, Autograph Collection
4.5 star property
Rock Harbor
8.8 out of 10, Excellent, (1002)
"Beautiful location, great views, very clean property, room was great (great bed), friendly staff."
United States
Scott
$392 nightly
The price is $441
Jan 19 - Jan 20, 2026
Total with taxes and fees
Playa Largo Resort & Spa, Autograph Collection
Private beach, white sand, sun loungers, beach towels
Chesapeake Beach Resort

Chesapeake Beach Resort

Chesapeake Beach Resort
3.5 star property
Matecumbe
9.2 out of 10, Wonderful, (1601)
"The entire resort was wonderful."
Canada
Mat
$237 nightly
The price is $267
Jan 6 - Jan 7, 2026
Total with taxes and fees
Chesapeake Beach Resort
Outdoor pool, open 7:00 AM to 11:00 PM, pool umbrellas, sun loungers
Holiday Inn Key Largo by IHG

Holiday Inn Key Largo by IHG

Holiday Inn Key Largo by IHG
3.0 star property
Key Largo
8.6 out of 10, Excellent, (1014)
"Wonderful hotel. Great location Pool is amazing the staff was very friendly In all very good.. highly recommend "
United States
Christopher
$189 nightly
The price is $213
Jan 4 - Jan 5, 2026
Total with taxes and fees
Holiday Inn Key Largo by IHG
Terrace/patio
Bayside Inn Key Largo

Bayside Inn Key Largo

Bayside Inn Key Largo
3.0 star property
Key Largo
8.6 out of 10, Excellent, (1625)
"Great location, Relaxing friendly atmosphere. Very basic room amenities but beautiful beach, pool, experience "
United States
Rebecca
$173 nightly
The price is $191
Jan 14 - Jan 15, 2026
Total with taxes and fees
Bayside Inn Key Largo
On the beach, sun loungers, snorkeling, kayaking
Drift Hotel

Drift Hotel

Drift Hotel
2.5 star property
Key Largo
9.0 out of 10, Wonderful, (1000)
"Always a great stay"
United States
Ashley
$153 nightly
The price is $172
Jan 4 - Jan 5, 2026
Total with taxes and fees
Drift Hotel
Sundeck
Rock Reef Resort

Rock Reef Resort

Rock Reef Resort
2.5 star property
Rock Harbor
9.2 out of 10, Wonderful, (1071)
"Great room, friendly staff "
United States
Chengdao
$137 nightly
The price is $155
Jan 6 - Jan 7, 2026
Total with taxes and fees
Rock Reef Resort
Terrace/patio
Waterside Suites & Marina

Waterside Suites & Marina

Waterside Suites & Marina
3.5 star property
Key Largo
9.0 out of 10, Wonderful, (1176)
"Always a great experience every time we go to key largo we stay there "
United States
AMYRSA
$149 nightly
The price is $168
Jan 15 - Jan 16, 2026
Total with taxes and fees
Waterside Suites & Marina
Marina
The Pelican Key Largo Cottages

The Pelican Key Largo Cottages

The Pelican Key Largo Cottages
2.0 star property
Key Largo
9.0 out of 10, Wonderful, (1003)
"Great place"
United States
Marc
$147 nightly
The price is $165
Jan 5 - Jan 6, 2026
Total with taxes and fees
The Pelican Key Largo Cottages
Aerial view
Dove Creek Resort & Marina, Trademark Collection by Wyndham

Dove Creek Resort & Marina, Trademark Collection by Wyndham

Dove Creek Resort & Marina, Trademark Collection by Wyndham
3.0 star property
Key Largo
7.6 out of 10, Good, (1005)
"Great room with beautiful sunrise over the ocean! "
Canada
Heather
$163 nightly
The price is $184
Jan 7 - Jan 8, 2026
Total with taxes and fees
Dove Creek Resort & Marina, Trademark Collection by Wyndham
Exterior
Marina Del Mar Resort and Marina

Marina Del Mar Resort and Marina

Marina Del Mar Resort and Marina
2.5 star property
Key Largo
8.4 out of 10, Very Good, (1661)
"Great location, amenities, service, places to eat. Very accommodating with extended stay."
United States
Joseph
$179 nightly
The price is $202
Jan 5 - Jan 6, 2026
Total with taxes and fees
Marina Del Mar Resort and Marina
Room, 1 King Bed, Bay View | Beach/ocean view
Hampton Inn Key Largo Manatee Bay

Hampton Inn Key Largo Manatee Bay

Hampton Inn Key Largo Manatee Bay
2.5 star property
Key Largo
8.8 out of 10, Excellent, (1004)
"Clean room, welcoming staff, nice stay."
Germany
Verena
$150 nightly
The price is $169
Jan 13 - Jan 14, 2026
Total with taxes and fees
Hampton Inn Key Largo Manatee Bay
Gazebo
Sunset Cove Beach Resort

Sunset Cove Beach Resort

Sunset Cove Beach Resort
2.5 star property
Key Largo
9.0 out of 10, Wonderful, (1003)
"Always a great stay"
United States
Richard
$187 nightly
The price is $211
Jan 8 - Jan 9, 2026
Total with taxes and fees
Sunset Cove Beach Resort
Exterior
Lime Tree Bay Resort

Lime Tree Bay Resort

Lime Tree Bay Resort
3.5 star property
Long Key
9.2 out of 10, Wonderful, (1108)
"This place is the best kept secret "
United States
Kathleen
$182 nightly
The price is $205
Jan 15 - Jan 16, 2026
Total with taxes and fees
Lime Tree Bay Resort
Private beach, sun loungers, beach umbrellas, beach towels
Cheeca Lodge & Spa

Cheeca Lodge & Spa

Cheeca Lodge & Spa
5.0 star property
Matecumbe
9.2 out of 10, Wonderful, (1277)
"Fabulous waterfront, activities, and dining as well as the staff. "
Canada
David
$328 nightly
The price is $370
Jan 4 - Jan 5, 2026
Total with taxes and fees
Cheeca Lodge & Spa
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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Stay near popular South Florida attractions

Windley Key Fossil Reef Geological State Park

4.3/5 (65 reviews)
Explore the fossilized reef of a former quarry in this island park, as you learn about the history and ecology from the interpretive trails.
See properties

Learn more about Windley Key

Check out the local area in Windley Key as you venture to sights like Windley Key Fossil Reef Geological State Park.

See all hotels in Windley Key
Windley Key Fossil Reef Geological State Park

Top Windley Key Hotel Reviews

Cheeca Lodge & Spa

Cheeca Lodge & Spa

10/10 Excellent
"The whole experience was amazing! Great amenities to keep us active and yet relaxed. My only concern was the plumbing quality. The flow in the shower was very weak and there was a smell (maybe mold or something). We stayed in a cabana away from the main lodge, so that may be why. Overall, loved the visit. Would definitely recommend and come back. "
Steve 5-night trip
Posted 9 hours ago
Cheeca Lodge & Spa

More cheap stays in Windley Key

Rock Reef Resort

Rock Reef Resort

97850 Overseas Hwy Key Largo FL
$137 nightly
The price is $155 total per night from Jan 6 to Jan 7
$155 total
Jan 6 - Jan 7, 2026
Total with taxes and fees
9.2/10 Wonderful! (1,069 reviews)

Hotels in Windley Key with star-rating

Explore a world of travel with Expedia