Hotels in Windley Key
Search over 2,738 hotels from $236
Earn Orbucks instantly: $1 Orbuck = $1 USD, good toward hotels
Save 10% or more on select hotels with Insider Prices
Book on the app to instantly earn 5% on 350,000+ hotels
Top Rated Windley Key Hotels

Three Waters Resort and Marina, Islamorada, a Tribute Portfolio Resort
84001 Overseas Hwy Islamorada FL
Free Cancellation
Reserve now, pay when you stay
1.23 mi from city center
$407 nightly
The price is $457 total per night
$457 total
Mar 23 - Mar 24
Total with taxes and fees
Three Waters Resort and Marina, Islamorada, a Tribute Portfolio Resort features a private beach, a marina, and 3 outdoor pools. Transportation is made easy with a free area shuttle. The 24-hour front desk has multilingual staff ready to assist with tours/tickets and luggage storage. If you like to take your furry friend along on your adventures, this pet-friendly property offers food and water bowls. Other amenities at this beach resort include a 24-hour gym, free WiFi in public areas, and meeting rooms.
On private beach
Pool

Fisher Inn Resort & Marina
84951 Overseas Hwy Islamorada FL
Free Cancellation
Reserve now, pay when you stay
0.54 mi from city center
$303 nightly
The price is $341 total per night
$341 total
Mar 11 - Mar 12
Total with taxes and fees
Guests staying at Fisher Inn Resort & Marina enjoy access to a private beach, an outdoor pool, and free WiFi in public areas. Free parking is available if you drive. Front-desk staff can assist with concierge services and luggage storage. Other amenities at this beach motel include coffee/tea in a common area, a microwave in a common area, and a refrigerator in a common area.
On private beach
Pool

Coconut Cove Resort and Marina
84801 Overseas Highway Islamorada FL
0.67 mi from city center
$389 nightly
The price is $438 total per night
$438 total
Mar 9 - Mar 10
Total with taxes and fees
Guests of Coconut Cove Resort and Marina enjoy a marina, an outdoor pool, and a children's pool. If you plan to drive, free parking is available. Front-desk staff can help with luggage storage, and provide local restaurant recommendations. Other amenities at this beach hotel include a gym, free WiFi in public areas, and a business center.
Pool
Breakfast included

Drop Anchor
84959 Overseas Highway, 222 Islamorada FL
0.44 mi from city center
$269 nightly
The price is $298 total per night
$298 total
Mar 11 - Mar 12
Total with taxes and fees
Guests of Drop Anchor enjoy an outdoor pool, free WiFi in public areas, and a business center. If you drive, put free parking to good use. Front-desk staff can help secure valuables, and provide local restaurant recommendations. Additional amenities include coffee/tea in a common area, free use of bicycles, and wedding services.
Pool
Pet friendly

Cheeca Lodge & Spa
81801 Overseas Highway, Mile Marker 82 Islamorada FL
Free Cancellation
Reserve now, pay when you stay
3.67 mi from city center
$388 nightly
The price is $437 total per night
$437 total
Mar 22 - Mar 23
Total with taxes and fees
Cheeca Lodge & Spa features a private beach, a golf course, and a full-service spa. Free valet and self parking are available, and there's also limo/town car service. The front desk has multilingual staff on hand 24/7 to help with securing valuables, luggage storage, and dry cleaning/laundry. Other amenities at this beach resort include 3 outdoor pools, a 24-hour gym, and a sauna.
On private beach
Pool

Chesapeake Beach Resort
83409 Overseas Hwy Islamorada FL
Free Cancellation
Reserve now, pay when you stay
1.82 mi from city center
$370 nightly
The price is $417 total per night
$417 total
Apr 6 - Apr 7
Total with taxes and fees
Chesapeake Beach Resort features a private beach, a marina, and 2 outdoor pools. The 24-hour front desk has multilingual staff ready to help with concierge services, and answer any questions about the area. Other amenities at this beach hotel include free WiFi in public areas, coffee/tea in a common area, and free use of bicycles.
On private beach
Pool

Reefhouse Resort & Marina
103800 Overseas Hwy Key Largo FL
17.64 mi from city center
$439 nightly
The price is $489 total per night
$489 total
Mar 9 - Mar 10
Total with taxes and fees
Reefhouse Resort & Marina features a private beach, a marina, and a full-service spa. You can put free parking to good use if you drive. The 24-hour front desk has multilingual staff ready to assist with luggage storage, concierge services, and dry cleaning/laundry. If you like to take your furry friend along on your adventures, this pet-friendly property offers food and water bowls. Other amenities at this beach hotel include an outdoor pool, a 24-hour gym, and WiFi in public areas.
On private beach
Pool

Baker's Cay Resort Key Largo, Curio Collection by Hilton
97000 Overseas Hwy Key Largo FL
10.79 mi from city center
$546 nightly
The price is $614 total per night
$614 total
Mar 12 - Mar 13
Total with taxes and fees
Guests of Baker's Cay Resort Key Largo, Curio Collection by Hilton have access to a private beach, 2 outdoor pools, and a gym. Valet parking is available for USD 35 per night, and there's also limo/town car service. The front desk has multilingual staff on hand 24/7 to help with tours or tickets, dry cleaning/laundry, and luggage storage. If you like to take your furry friend along on your adventures, this pet-friendly property offers food and water bowls. Other amenities at this beach resort include a hot tub, a conference center, and a 24-hour business center.
On private beach
Pool

Lime Tree Bay Resort
68500 Overseas Hwy Long Key FL
16.57 mi from city center
$299 nightly
The price is $336 total per night
$336 total
Mar 9 - Mar 10
Total with taxes and fees
At Lime Tree Bay Resort, guests have access to a private beach, 3 outdoor pools, and free WiFi in public areas. If you drive, take advantage of free parking. The front desk has multilingual staff that can help with securing valuables and tours/tickets. If you like to take your furry friend along on your adventures, this pet-friendly property offers food and water bowls. Other amenities at this beach resort include an outdoor tennis court, coffee/tea in a common area, and free use of bicycles.
On private beach
Pool

Bayside Inn Key Largo
99490 Overseas Hwy Key Largo FL
Free Cancellation
Reserve now, pay when you stay
13.49 mi from city center
$254 nightly
The price is $282 total per night
$282 total
Mar 10 - Mar 11
Total with taxes and fees
Guests of Bayside Inn Key Largo enjoy a private beach, an outdoor pool, and a 24-hour gym. Free parking is included with your stay. The front desk has multilingual staff on hand 24/7 to help with tours or tickets, securing valuables, and luggage storage. If you like to take your furry friend along on your adventures, this pet-friendly property offers food and water bowls. Other amenities at this beach hotel include free WiFi in public areas, a business center, and coffee/tea in a common area.
On private beach
Pool

Waterside Suites & Marina
201 Ocean Drive Key Largo FL
Free Cancellation
Reserve now, pay when you stay
13.93 mi from city center
$209 nightly
The price is $236 total per night
$236 total
Mar 9 - Mar 10
Total with taxes and fees
Guests staying at Waterside Suites & Marina enjoy access to a marina, an outdoor pool, and free WiFi in public areas. Limited parking is available. The 24-hour front desk has staff standing by to help with luggage storage, tours or tickets, and securing valuables. If you like to take your furry friend along on your adventures, this pet-friendly property offers food and water bowls. Additional amenities include free newspapers, a terrace, and laundry facilities.
Pool
Pet friendly

Marina Del Mar Resort and Marina
527 Caribbean Drive Key Largo FL
Free Cancellation
Reserve now, pay when you stay
13.78 mi from city center
$226 nightly
The price is $255 total per night
$255 total
Mar 9 - Mar 10
Total with taxes and fees
Guests of Marina Del Mar Resort and Marina enjoy a marina, an outdoor pool, and a gym. If you drive, take advantage of free parking. The front desk has multilingual staff that can help secure valuables, and offer advice about sights and eateries nearby. Additional amenities include free WiFi in public areas, a hot tub, and conference space.
Pool
Hot Tub
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.
How much is a Windley Key hotel?
Check Windley Key hotel room prices by star rating

5 Star Hotels
3 properties
Windley Key hotels essential information
Accommodation | 2,738 hotels |
|---|---|
Lowest Price | $236 |
Highest Price | $614 |
Popular hotels | Three Waters Resort and Marina, Islamorada, a Tribute Portfolio Resort, Fisher Inn Resort & Marina, Coconut Cove Resort and Marina, Drop Anchor, Cheeca Lodge & Spa, Chesapeake Beach Resort, Reefhouse Resort & Marina, Baker's Cay Resort Key Largo, Curio Collection by Hilton, Lime Tree Bay Resort, Bayside Inn Key Largo, Waterside Suites & Marina, Marina Del Mar Resort and Marina |
Recent Reviews

Chesapeake Beach Resort
4/5 Good
"Nice updates with large decks. Breakfast is very good"
A verified traveler stayed at Chesapeake Beach Resort
Posted 4 hours ago
More to Explore
More to Explore
- Hotels near Harry Harris Park
- Hotels near MarineLab Undersea Laboratory
- Key Largo Hotels
- Hotels near Long Key State Park
- Matecumbe Hotels
- Hotels near Anne's Beach
- Hotels near Caribbean Club Bar
- 4 Star Hotels in Islamorada
- 5 Star Hotels in Islamorada
- Apartments in Islamorada
- Condo Rentals in Islamorada
- Cottages in Islamorada
- Extended Stay Hotels in Islamorada
- Guest Houses in Islamorada
- Beach Resorts & in Islamorada
- Cheap Hotels in Islamorada
- Kid Friendly Hotels in Islamorada
- Gay Friendly Hotels in Islamorada
- Golf Resorts & in Islamorada
- Historic Hotels in Islamorada
- Hotels with Pool in Islamorada
- Hotels with WiFi in Islamorada
- Hotels with Bar in Islamorada
- Hotels with Childcare in Islamorada
- Hotels with Free Breakfast in Islamorada
- Hotels with Free Parking in Islamorada
- Hotels with Hot Tubs in Islamorada
- Hotels with Kitchenettes in Islamorada
- Hotels with Room Service in Islamorada
- Hotels with Tennis Courts in Islamorada
- Luxury Hotels in Islamorada
- Oceanfront Hotels in Islamorada
- Pet Friendly Hotels in Islamorada
- Romantic Getaways & Hotels in Islamorada
- Hotels with Shopping in Islamorada
- Spa Resorts & in Islamorada
- Islamorada Hotels
- Houseboats in Islamorada
- Inns in Islamorada
- Motels in Islamorada
- Vacation Homes in Islamorada
- Rv Parks in Islamorada
- Resorts in Islamorada
- Villas in Islamorada
- Hotels near Jacob's Aquatic Center
- Anglers Park Hotels
- Hotels near Bluefin Rock Harbor Marina
- Hotels near Fiesta Key
- Hotels near Windley Key Fossil Reef Geological State Park
- Hotels near Florida Keys Dive Center
- Hotels near Florida Keys Brewing Co.
- Hotels near Founders Park
- Hotels near Matecumbe United Methodist Church
- Hotels near Key Largo Baptist Church
- Sexton Cove Estates Hotels
- Hotels near Sunset Drive Beach
- Lignumvitae Key Botanical State Park Hotels
- Hotels near Jimmy Johnson's Big Chill
- Hotels near Islamorada County Park
- Key Largo Village Hotels
- Hotels near Hurricane Monument
- Indian Waterways Hotels
- Cheap Hotels in Venetian Shores
- Hotels with Pool in Venetian Shores
- Long Key Hotels
- 5 Star Hotels in Plantation Key
- Hotels with a Gym in Plantation Key
- Tavernier Hotels
- Hotels near Bud n' Mary's Dive Center
- Hotels near Pigeon Key
- Flights to Miami
- Flights to Islamorada
- Flights from Islamorada
- Flights from Austin to Islamorada
- Flights from Charlotte to Islamorada
- Flights from Chicago to Islamorada
- Flights from Cleveland to Islamorada
- Flights from Denver to Islamorada
- Flights from Detroit to Islamorada
- Flights from Houston to Islamorada
- Flights from Indianapolis to Islamorada
- Flights from Los Angeles to Islamorada
- Flights from Memphis to Islamorada
- Flights from Mexico City to Islamorada
- Flights from Minneapolis - St. Paul to Islamorada
- Flights from New Orleans to Islamorada
- Flights from New York to Islamorada
- Flights from Philadelphia to Islamorada
- Flights from Raleigh to Islamorada
- Flights from Washington to Islamorada
- Flights from Pittsburgh to Islamorada
- Flights from Newark to Islamorada
- Flights from Richmond to Islamorada
- Flights from Halifax to Islamorada
- Flights from Covington to Islamorada
- Beach Hotels in Islamorada
- Resorts in Islamorada
- Pet-friendly Hotels in Islamorada
- Houseboats in Islamorada
- Hotels in Islamorada
- Luxury Hotels in Islamorada
- Flights to Islamorada
- Islamorada vacations
- Oceanfront Hotels in Islamorada
- Cottages in Islamorada
- Cheap Hotels in Islamorada
- Motels in Islamorada
- Islamorada vacation rentals
- Hotels in Plantation Key
- Visit Founders Park






