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Featured Windley Key 2 Stars 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
$322 nightly
The price is $362 total per night
$362 total
May 25 - May 26
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
$198 nightly
The price is $223 total per night
$223 total
Apr 28 - Apr 29
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 luggage storage and concierge services. 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
$179 nightly
The price is $201 total per night
$201 total
Apr 26 - Apr 27
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. 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
$210 nightly
The price is $232 total per night
$232 total
Apr 26 - Apr 27
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 barbecue grills.
Pool
Pet friendly

Chesapeake Beach Resort
83409 Overseas Hwy Islamorada FL
Free Cancellation
Reserve now, pay when you stay
1.82 mi from city center
$232 nightly
The price is $261 total per night
$261 total
May 10 - May 11
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

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
$312 nightly
The price is $351 total per night
$351 total
May 10 - May 11
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 dry cleaning/laundry, tours or tickets, and securing valuables. Other amenities at this beach resort include 3 outdoor pools, a 24-hour gym, and a sauna.
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
$360 nightly
The price is $405 total per night
$405 total
May 26 - May 27
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. 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 tours or tickets, dry cleaning/laundry, 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 hot tub, a conference center, and a 24-hour business center.
On private beach
Pool

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
$151 nightly
The price is $170 total per night
$170 total
Apr 26 - Apr 27
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

Waterside Suites & Marina
201 Ocean Drive Key Largo FL
Free Cancellation
Reserve now, pay when you stay
13.93 mi from city center
$146 nightly
The price is $164 total per night
$164 total
May 4 - May 5
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 securing valuables, luggage storage, and concierge services. 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
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 essential information
Accommodation | 2,729 hotels |
|---|---|
Lowest Price | $164 |
Highest Price | $405 |
Popular hotels | Three Waters Resort and Marina, Islamorada, a Tribute Portfolio Resort, Fisher Inn Resort & Marina, Coconut Cove Resort and Marina, Drop Anchor, Marina Del Mar Resort and Marina, Baker's Cay Resort Key Largo, Curio Collection by Hilton, Cheeca Lodge & Spa, Chesapeake Beach Resort, Waterside Suites & Marina |
Recent Reviews

Baker's Cay Resort Key Largo, Curio Collection by Hilton
5/5 Excellent
"Both beach and mangrove was spectacular! "
A verified traveler stayed at Baker's Cay Resort Key Largo, Curio Collection by Hilton
Posted 9 hours ago
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