Hotels in Windley Key

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Dec 3 - Dec 4
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Dec 4 - Dec 5
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Top Rated Windley Key Hotels

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
Free Cancellation
Reserve now, pay when you stay
1.23 mi from city center
$254 nightly
The price is $285 total per night
$285 total
Dec 17 - Dec 18
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

Fisher Inn Resort & Marina

3.5 out of 5
84951 Overseas Hwy Islamorada FL
0.53 mi from city center
$113 nightly
The price is $127 total per night
$127 total
Dec 18 - Dec 19
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

Coconut Cove Resort and Marina

3 out of 5
84801 Overseas Highway Islamorada FL
0.67 mi from city center
$140 nightly
The price is $158 total per night
$158 total
Dec 4 - Dec 5
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

Drop Anchor

3 out of 5
84959 Overseas Highway, 222 Islamorada FL
0.44 mi from city center
$130 nightly
The price is $142 total per night
$142 total
Dec 4 - Dec 5
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 a garden.
Pool
Pet friendly
Chesapeake Beach Resort

Chesapeake Beach Resort

3.5 out of 5
83409 Overseas Hwy Islamorada FL
Free Cancellation
Reserve now, pay when you stay
1.82 mi from city center
$178 nightly
The price is $201 total per night
$201 total
Dec 17 - Dec 18
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
Lime Tree Bay Resort

Lime Tree Bay Resort

3.5 out of 5
68500 Overseas Hwy Long Key FL
Free Cancellation
Reserve now, pay when you stay
16.62 mi from city center
$179 nightly
The price is $201 total per night
$201 total
Dec 15 - Dec 16
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 tours/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. 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
Cheeca Lodge & Spa

Cheeca Lodge & Spa

5 out of 5
81801 Overseas Highway, Mile Marker 82 Islamorada FL
Free Cancellation
Reserve now, pay when you stay
3.67 mi from city center
$240 nightly
The price is $271 total per night
$271 total
Dec 18 - Dec 19
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 concierge services, securing valuables, and luggage storage. Other amenities at this beach resort include 3 outdoor pools, a 24-hour gym, and a sauna.
On private beach
Pool
Reefhouse Resort & Marina

Reefhouse Resort & Marina

3.5 out of 5
103800 Overseas Hwy Key Largo FL
Free Cancellation
Reserve now, pay when you stay
17.64 mi from city center
$269 nightly
The price is $298 total per night
$298 total
Dec 14 - Dec 15
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 securing valuables, dry cleaning/laundry, and concierge services. 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
Amara Cay Resort

Amara Cay Resort

4 out of 5
80001 Overseas Hwy Islamorada FL
5.46 mi from city center
$250 nightly
The price is $282 total per night
$282 total
Dec 10 - Dec 11
Total with taxes and fees
At Amara Cay Resort, guests enjoy a private beach, an outdoor pool, and a gym. The 24-hour front desk has multilingual staff ready to help with luggage storage, and answer any questions about the area. 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 meeting room, a terrace, and laundry facilities.
On private beach
Pool
The Pelican Key Largo Cottages

The Pelican Key Largo Cottages

2 out of 5
99340 Overseas Highway Key Largo FL
Free Cancellation
Reserve now, pay when you stay
13.33 mi from city center
$110 nightly
The price is $123 total per night
$123 total
Dec 9 - Dec 10
Total with taxes and fees
At The Pelican Key Largo Cottages, guests have access to a private beach, a marina, and free WiFi in public areas. You can take advantage of free parking if you drive. The front desk has multilingual staff that can help with concierge services and luggage storage. Other amenities at this beach hotel include meeting rooms, a computer station, and free newspapers.
On private beach
Parking included
Playa Largo Resort & Spa, Autograph Collection

Playa Largo Resort & Spa, Autograph Collection

4.5 out of 5
97450 Overseas Highway Key Largo FL
Free Cancellation
Reserve now, pay when you stay
11.53 mi from city center
$312 nightly
The price is $351 total per night
$351 total
Dec 15 - Dec 16
Total with taxes and fees
Guests of Playa Largo Resort & Spa, Autograph Collection have access to a marina, a full-service spa, and an outdoor pool. Valet parking is offered for USD 39.38 per night. Multilingual staff at the 24-hour front desk can assist with access to locker space, luggage storage, and securing valuables. 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 a hot tub.
Pool
Hot Tub
Baker's Cay Resort Key Largo, Curio Collection by Hilton

Baker's Cay Resort Key Largo, Curio Collection by Hilton

4 out of 5
97000 Overseas Hwy Key Largo FL
Free Cancellation
Reserve now, pay when you stay
10.79 mi from city center
$302 nightly
The price is $340 total per night
$340 total
Dec 15 - Dec 16
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 39.20 per night, and there's also limo/town car service. The front desk has multilingual staff on hand 24/7 to help with securing valuables, 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 resort include a hot tub, a conference center, and a 24-hour business center.
On private beach
Pool
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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.
Windley Key Hotels

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Windley Key hotels essential information

Accommodation
2,784 hotels
Lowest Price
$123
Highest Price
$351
Popular hotels
Three Waters Resort and Marina, Islamorada, a Tribute Portfolio Resort, Fisher Inn Resort & Marina, Coconut Cove Resort and Marina, Drop Anchor, Chesapeake Beach Resort, Lime Tree Bay Resort, Cheeca Lodge & Spa, Reefhouse Resort & Marina, Amara Cay Resort, The Pelican Key Largo Cottages, Playa Largo Resort & Spa, Autograph Collection, Baker's Cay Resort Key Largo, Curio Collection by Hilton

Recent Reviews

Chesapeake Beach Resort

Chesapeake Beach Resort

5/5 Excellent
"Great place"
A verified traveler stayed at Chesapeake Beach Resort
Posted 5 days ago
Chesapeake Beach Resort

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