Book 2 Star Hotels in Windley Key
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
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
$364 nightly
The price is $410 total per night
$410 total
Jan 28 - Jan 29
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

Coconut Cove Resort and Marina
84801 Overseas Highway Islamorada FL
0.67 mi from city center
$249 nightly
The price is $280 total per night
$280 total
Jan 20 - Jan 21
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

Fisher Inn Resort & Marina
84951 Overseas Hwy Islamorada FL
Free Cancellation
Reserve now, pay when you stay
0.54 mi from city center
$222 nightly
The price is $249 total per night
$249 total
Jan 21 - Jan 22
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

Drop Anchor
84959 Overseas Highway, 222 Islamorada FL
0.44 mi from city center
$192 nightly
The price is $212 total per night
$212 total
Jan 21 - Jan 22
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 vending machine.
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
$241 nightly
The price is $272 total per night
$272 total
Jan 27 - Jan 28
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

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
$156 nightly
The price is $176 total per night
$176 total
Jan 25 - Jan 26
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
$165 nightly
The price is $186 total per night
$186 total
Jan 21 - Jan 22
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, 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
16.57 mi from city center
$199 nightly
The price is $224 total per night
$224 total
Jan 21 - Jan 22
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

Reefhouse Resort & Marina
103800 Overseas Hwy Key Largo FL
Free Cancellation
Reserve now, pay when you stay
17.64 mi from city center
$309 nightly
The price is $343 total per night
$343 total
Jan 20 - Jan 21
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, 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
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 | 2,763 hotels |
|---|---|
Lowest Price | $176 |
Highest Price | $410 |
Popular hotels | Three Waters Resort and Marina, Islamorada, a Tribute Portfolio Resort, Coconut Cove Resort and Marina, Fisher Inn Resort & Marina, Drop Anchor, Chesapeake Beach Resort, Lime Tree Bay Resort, Waterside Suites & Marina, Marina Del Mar Resort and Marina, Reefhouse Resort & Marina |
Recent Reviews

Chesapeake Beach Resort
5/5 Excellent
"It was very nice place to stay resort nice and clean the ataff Vanessa very helpful and sweet. We very happy will come back again. Thank you Vanessa again ."
A verified traveler stayed at Chesapeake Beach Resort
Posted 3 days ago
More to Explore
- 5 Star Hotels in Plantation Key
- Hotels with a Gym in Plantation Key
- 3 Star Hotels in Marathon
- 4 Star Hotels in Marathon
- 5 Star Hotels in Tingler Island
- Hotels near Islamorada County Park
- 4 Star Hotels in Conch Key
- 5 Star Hotels in Conch Key
- 4 Star Hotels in Long Key
- 2 Star Hotels in Rock Harbor
- 5 Star Hotels in Rock Harbor
- 5 Star Hotels in Cutler Bay
- 3 Star Hotels in Islamorada
- 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
- 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
- 3 Star Hotels in Duck Key
- 4 Star Hotels in Duck Key
- 5 Star Hotels in Duck Key
- 3 Star Hotels in North Key Largo
- 4 Star Hotels in North Key Largo
- 5 Star Hotels in North Key Largo
- 3 Star Hotels in Florida City
- 5 Star Hotels in Florida City
- 5 Star Hotels in Coral Lagoon
- 5 Star Hotels in Key Largo Park
- 4 Star Hotels in Key Colony Beach
- Hotels near Founders Park
- 4 Star Hotels in Naranja
- Hotels near Windley Key Fossil Reef Geological State Park
- 3 Star Hotels in Tavernier
- 4 Star Hotels in Tavernier
- 5 Star Hotels in Homestead
- Cheap Hotels in Venetian Shores
- Hotels with Pool in Venetian Shores
- 5 Star Hotels in Lower Matecumbe Key
- 4 Star Hotels in Key Largo
- 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
- Flights to Miami
- Islamorada vacation rentals
- Houseboats in Islamorada
- Oceanfront Hotels in Islamorada
- Resorts in Islamorada
- Islamorada vacations
- Hotels in Plantation Key
- Luxury Hotels in Islamorada
- Beach Hotels in Islamorada
- Pet-friendly Hotels in Islamorada
- Visit Founders Park
- Flights to Islamorada
- Cottages in Islamorada
- Motels in Islamorada
- Hotels in Islamorada
- Cheap Hotels in Islamorada


