Hotels in Windley Key
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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
The price is $388 total per night
$388 total
per night
Jun 21 - Jun 22
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 luggage storage 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 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
The price is $212 total per night
$212 total
per night
Jun 15 - Jun 16
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
The price is $201 total per night
$201 total
per night
Jun 14 - Jun 15
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. Helpful staff is there to provide front-desk service during limited hours, as well as offer insight about the area. 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
The price is $176 total per night
$176 total
per night
Jun 14 - Jun 15
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 picnic area.
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
The price is $342 total per night
$342 total
per night
Jun 15 - Jun 16
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 tours or tickets, luggage storage, and securing valuables. Other amenities at this beach resort include 3 outdoor pools, a 24-hour gym, and a sauna.
On private beach
Pool

Reefhouse Resort & Marina
103800 Overseas Hwy Key Largo FL
Free Cancellation
Reserve now, pay when you stay
17.64 mi from city center
The price is $264 total per night
$264 total
per night
Jun 21 - Jun 22
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 concierge services, luggage storage, 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

Chesapeake Beach Resort
83409 Overseas Hwy Islamorada FL
Free Cancellation
Reserve now, pay when you stay
1.82 mi from city center
The price is $258 total per night
$258 total
per night
Jun 18 - Jun 19
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

Baker's Cay Resort Key Largo, Curio Collection by Hilton
97000 Overseas Hwy Key Largo FL
Free Cancellation
Reserve now, pay when you stay
10.79 mi from city center
The price is $332 total per night
$332 total
per night
Jun 22 - Jun 23
Guests of Baker's Cay Resort Key Largo, Curio Collection by Hilton have access to a private beach, 2 outdoor pools, and a gym. Parking is available for USD 23 per night (USD 35 per night for valet parking), and there's also limo/town car service. The front desk has multilingual staff on hand 24/7 to help with luggage storage, securing valuables, 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

Waterside Suites & Marina
201 Ocean Drive Key Largo FL
Free Cancellation
Reserve now, pay when you stay
13.93 mi from city center
The price is $176 total per night
$176 total
per night
Jun 14 - Jun 15
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 securing valuables, tours or 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. Additional amenities include free newspapers, a terrace, and laundry facilities.
Pool
Pet friendly

Lime Tree Bay Resort
68500 Overseas Hwy Long Key FL
Free Cancellation
Reserve now, pay when you stay
16.57 mi from city center
The price is $224 total per night
$224 total
per night
Jun 14 - Jun 15
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

Islander Resort
82100 Overseas Highway Islamorada FL
Free Cancellation
Reserve now, pay when you stay
3.36 mi from city center
The price is $356 total per night
$356 total
per night
Jun 21 - Jun 22
Guests of Islander Resort have access to a private beach, 2 outdoor pools, and a 24-hour gym. Free parking is available if you drive. The 24-hour front desk has multilingual staff ready to assist with dry cleaning/laundry, concierge services, 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, meeting rooms, and a conference center.
On private beach
Pool

Amara Cay Resort
80001 Overseas Hwy Islamorada FL
Free Cancellation
Reserve now, pay when you stay
5.46 mi from city center
The price is $278 total per night
$278 total
per night
Jul 7 - Jul 8
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
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
2 properties
Windley Key hotels essential information
Accommodation | 2,714 hotels |
|---|---|
Lowest Price | $176 |
Highest Price | $388 |
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, Reefhouse Resort & Marina, Chesapeake Beach Resort, Baker's Cay Resort Key Largo, Curio Collection by Hilton, Waterside Suites & Marina, Lime Tree Bay Resort, Islander Resort, Amara Cay Resort |
Recent Reviews

Cheeca Lodge & Spa
5/5 Excellent
"Ok"
A verified traveler stayed at Cheeca Lodge & Spa
Posted 23 hours ago
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