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Find hotels in Windley Key, FL from CA $164

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Our top choices for Windley Key hotels

1. Drop Anchor

Drop Anchor
3.0 star property
Islamorada
8.8 out of 10, Excellent, (1,013 reviews)
"We really enjoyed the laid back vibe, matched with the amenities and the location. We had a great stay!"
United States
Noel
The price is CA $159
CA $228 total
includes taxes & fees
Aug 3 - Aug 4
Drop Anchor

2. Fisher Inn Resort & Marina

Fisher Inn Resort & Marina
3.5 star property
Islamorada
8.2 out of 10, Very good, (1,009 reviews)
"Was a very nice property, great location, great value."
United States
Gary
The price is CA $150
CA $215 total
includes taxes & fees
Aug 10 - Aug 11
Fisher Inn Resort & Marina

3. Three Waters Resort and Marina, Islamorada, a Tribute Portfolio Resort

Three Waters Resort and Marina, Islamorada, a Tribute Portfolio Resort
4.0 star property
Islamorada
9.0 out of 10, Wonderful, (238 reviews)
"Wonderful resort and friendly staff!"
United States
Ana
The price is CA $292
CA $432 total
includes taxes & fees
Aug 12 - Aug 13
Three Waters Resort and Marina, Islamorada, a Tribute Portfolio Resort

4. Coconut Cove Resort and Marina

Coconut Cove Resort and Marina
3.0 star property
Islamorada
9.0 out of 10, Wonderful, (278 reviews)
"Amazing staff! Clancy is great! This place is so cute family oriented and friendly! I cant wait to stay here again!"
United States
Lisa C
The price is CA $267
CA $300 total
includes taxes & fees
Aug 2 - Aug 3
Coconut Cove Resort and Marina

5. The Ocean View Inn & Pub

The Ocean View Inn & Pub
2.0 star property
Islamorada
9.0 out of 10, Wonderful, (26 reviews)
"Food was excellent and the staff was delightful. Very accommodating"
United States
Mark
The price is CA $263
CA $296 total
includes taxes & fees
Aug 4 - Aug 5
The Ocean View Inn & Pub

6. Chesapeake Beach Resort

Chesapeake Beach Resort
3.5 star property
Matecumbe
9.2 out of 10, Wonderful, (1,771 reviews)
"Nice place 👌"
United States
Cristina
The price is CA $213
CA $319 total
includes taxes & fees
Aug 3 - Aug 4
Chesapeake Beach Resort

7. Hadley Resort and Marina

Hadley Resort and Marina
3.5 star property
Matecumbe
7.6 out of 10, Good, (1,001 reviews)
"Booked this on Expedia based on location alone- GREAT CHOICE. Lot of help from team (thanks Eric) very unique and ‘kitschy’ in a great location. Loved it here although we were one night only."
United States
Bill
The price is CA $143
CA $207 total
includes taxes & fees
Aug 2 - Aug 3
Hadley Resort and Marina

8. Cheeca Lodge & Spa

Cheeca Lodge & Spa
5.0 star property
Matecumbe
9.2 out of 10, Wonderful, (1,363 reviews)
"Great place!!"
United States
David
The price is CA $203
CA $331 total
includes taxes & fees
Aug 12 - Aug 13
Cheeca Lodge & Spa

9. La Jolla Resort

La Jolla Resort
2.5 star property
Matecumbe
9.2 out of 10, Wonderful, (1,001 reviews)
"Good location and great staff"
United States
adrian
The price is CA $176
CA $238 total
includes taxes & fees
Aug 13 - Aug 14
La Jolla Resort

10. Islander Resort

Islander Resort
4.0 star property
Matecumbe
9.4 out of 10, Exceptional, (1,088 reviews)
"Can't wait to stay there again!"
United States
Sarah
The price is CA $368
CA $509 total
includes taxes & fees
Aug 12 - Aug 13
Islander Resort

11. Amara Cay Resort

Amara Cay Resort
4.0 star property
Matecumbe
8.8 out of 10, Excellent, (1,312 reviews)
"Beautiful hotel, amazing views , very friendly staff, I will definitely return to Amara cay"
United States
Estefani
The price is CA $228
CA $359 total
includes taxes & fees
Aug 12 - Aug 13
Amara Cay Resort

12. Creekside Inn

Creekside Inn
2.5 star property
Tavernier
7.8 out of 10, Good, (1,009 reviews)
"Great place to stay!!!!"
United States
Cristy
The price is CA $202
CA $227 total
includes taxes & fees
Aug 16 - Aug 17
Creekside Inn

13. Drift Hotel

Drift Hotel
2.5 star property
Key Largo
9.0 out of 10, Wonderful, (1,003 reviews)
"Very nice a cozy hotel . Location is perfect for boating . Our children enjoyed the kayak and the amenities . Five star"
United States
oscar
The price is CA $179
CA $218 total
includes taxes & fees
Aug 2 - Aug 3
Drift Hotel

14. Ragged Edge Resort & Marina

Ragged Edge Resort & Marina
2.5 star property
Islamorada
9.4 out of 10, Exceptional, (260 reviews)
"Clean and quiet"
United States
cheryl
The price is CA $267
CA $300 total
includes taxes & fees
Aug 3 - Aug 4
Ragged Edge Resort & Marina

15. Breezy Palms Resort

Breezy Palms Resort
2.5 star property
Matecumbe
8.8 out of 10, Excellent, (713 reviews)
"my 2nd time staying here and i will be back for a 3rd"
United States
Tristan
The price is CA $129
CA $219 total
includes taxes & fees
Aug 10 - Aug 11
Breezy Palms Resort

16. Ocean Pointe Suites at Key Largo

Ocean Pointe Suites at Key Largo
3.5 star property
Tavernier
8.4 out of 10, Very good, (1,018 reviews)
"Excellent clean and well kept property close to great restaurants and in the middle of the keys."
United States
Adalyn
The price is CA $181
CA $229 total
includes taxes & fees
Aug 24 - Aug 25
Ocean Pointe Suites at Key Largo

17. Treasure Harbor

Treasure Harbor
3.0 star property
Islamorada
9.0 out of 10, Wonderful, (166 reviews)
"The houseboat were a great experience not only for the kid's but the adults also. Seeing the manatees swim around the cove was awesome! It was a great place to meet your neighbors as the porches are very close. The swimming pool is a great addition to the property! If going back to the area, I would definitely go there again! We really enjoyed our visit there!"
United States
Kelly
The price is CA $215
CA $440 total
includes taxes & fees
Aug 16 - Aug 17
Treasure Harbor

18. Dove Creek Resort & Marina, Trademark Collection by Wyndham

Dove Creek Resort & Marina, Trademark Collection by Wyndham
3.0 star property
Key Largo
7.8 out of 10, Good, (1,000 reviews)
"Very nice place"
United States
Mae L
The price is CA $176
CA $243 total
includes taxes & fees
Aug 11 - Aug 12
Dove Creek Resort & Marina, Trademark Collection by Wyndham

19. Coconut Palm Inn

Coconut Palm Inn
3.0 star property
Tavernier
9.4 out of 10, Exceptional, (550 reviews)
"So happy with the stay, everything was clean and spacious. This is a little treasure nested in the keys. Can’t wait to be back"
United States
judith
The price is CA $265
CA $354 total
includes taxes & fees
Aug 2 - Aug 3
Coconut Palm Inn

20. Hampton Inn Key Largo Manatee Bay

Hampton Inn Key Largo Manatee Bay
2.5 star property
Key Largo
8.8 out of 10, Excellent, (1,042 reviews)
"Nice place to stay"
United States
Ricardo
The price is CA $206
CA $232 total
includes taxes & fees
Aug 9 - Aug 10
Hampton Inn Key Largo Manatee Bay
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.
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Stay near popular Windley Key attractions

Learn more about Windley Key

Check out the local area in Windley Key—home to attractions like Windley Key Fossil Reef Geological State Park and Hog Heaven.

An archaeological site with stone structures and metal machinery.

Top Windley Key Hotel Reviews

More cheap stays in Windley Key

Hotels in Windley Key with star rating

Find out more about Windley Key

Top reasons to visit Windley Key

  • Outdoor Adventures: Windley Key is a paradise for outdoor enthusiasts, featuring scenic hiking trails and engaging virtual tours.
  • Windley Key State Park: A highlight for nature lovers, offering stunning landscapes and opportunities for exploration.
  • Fossil Reef Discovery: Experience the unique Windley Key Fossil Reef, a fascinating glimpse into the area's geological history.
  • Nearby Beaches: Relax on beautiful beaches in Islamorada, just a short distance away, enhancing your coastal experience.
  • Diverse Accommodations: Choose from a range of lodging options, from budget-friendly to luxurious, accommodating every traveler's needs.

Find great hotels near Windley Key

Discover the charm of Windley Key, Florida, where a variety of hotel accommodations cater to every traveler's preference. From budget-friendly options to luxurious resorts, you can find the perfect stay, whether you're seeking adventure, a beach getaway, or pet-friendly lodgings. Explore Windley Key vacation rentals and experience the beauty of Florida’s Keys while enjoying comfortable amenities tailored to make your holiday unforgettable.

  • Amara Cay Resort: Nestled 8.0km away from Windley Key, Amara Cay Resort is a family-friendly, 3.5-star beachside haven ideal for adventure seekers and families alike. With direct beach access, guests can immerse themselves in a variety of outdoor activities, from onsite kayaking and snorkelling to nearby hiking and biking trails. The resort ensures a worry-free stay for families with amenities like cribs and a first aid kit. Amara Cay provides a perfect blend of relaxation and adventure, making it an excellent choice for those looking to create lasting memories.
  • Cheeca Lodge & Spa: Located just 6.4km from Windley Key, Cheeca Lodge & Spa is a luxurious 4-star resort that caters to beach lovers and golf enthusiasts. This stunning property offers direct access to the beach and features a scenic golf course for guests to enjoy. Adventure awaits with onsite windsurfing and fishing, while nearby hiking opportunities abound. The resort combines elegance with a laid-back atmosphere, providing a variety of dining options and a full-service spa for a truly indulgent experience. It’s the perfect retreat for those seeking both relaxation and excitement.
  • Islander Resort: Just 4.8km from Windley Key, Islander Resort is a charming 3-star hotel that caters to families and adventure seekers. With direct beach access, guests can partake in an array of watersports, including kayaking and parasailing. The resort also features family-friendly amenities such as onsite mini-golf and ping pong, ensuring entertainment for all ages. Whether you’re looking to relax on the beach or explore the local waters, Islander Resort provides a fun-filled atmosphere perfect for creating unforgettable holiday experiences.

Where to stay near Windley Key

Windley Key, nestled in the stunning Florida Keys, offers an idyllic getaway for those seeking outdoor adventures and relaxation. With its family-friendly atmosphere and romantic settings, visitors can explore the enchanting landscapes of the Upper Florida Keys. Nearby, the charming village of Islamorada beckons with its beautiful beaches and vibrant local culture. Whether you're diving into the crystal-clear waters or lounging on the shore, Windley Key promises an unforgettable vacation experience.

  • Islamorada: Known as the "Village of Islands," Islamorada is a picturesque destination that offers stunning coastal views and a laid-back atmosphere. Located directly on Windley Key, this city is a haven for outdoor enthusiasts and families looking to escape the hustle and bustle. Visitors can enjoy a variety of activities, from relaxing on beautiful beaches to exploring shopping areas and local resorts. The peak travel seasons, from March to April and July, see a vibrant influx of tourists, creating a lively ambiance perfect for family fun and adventure. Key landmarks include pristine beaches and a lively tourist precinct that add to its charm.
  • Tavernier: Just 9.7km from Windley Key, Tavernier is a quaint city that captures the heart of the Florida Keys. With a focus on outdoor activities and family adventures, Tavernier is an ideal spot for those looking to immerse themselves in nature. The peak tourist seasons are similar to its neighbour, with March to April and July drawing the most visitors. Guests can explore local shopping areas and enjoy the beautiful beaches nearby. The town is surrounded by lush landscapes and offers easy access to various recreational activities, making it a perfect addition to your itinerary.
  • Venetian Shores: Nestled only 805m from Windley Key, Venetian Shores is a charming neighbourhood that boasts a relaxed vibe and a strong sense of community. This area is less seasonal, attracting visitors year-round, with peak times in February to March and July. Families and outdoor lovers will find plenty to enjoy, from recreational areas to beautiful beaches. The local shopping options and nearby islands provide a delightful experience for all. Venetian Shores is perfect for those seeking a tranquil getaway without straying too far from the attractions of the Florida Keys.

Things to do near Windley Key

Windley Key offers a fantastic outdoor getaway, perfect for adventure seekers. Explore scenic hiking trails, enjoy a leisurely walk through beautiful landscapes, or take part in engaging virtual tours. With its stunning natural beauty, Windley Key invites you to immerse yourself in various outdoor activities, making it an ideal destination for your vacation.

Shopping

For shopping in Windley Key, visit Rain Barrel Village, a charming spot just 1.6km away, offering a family-friendly atmosphere. If you're up for a drive, check out Kiffney's Firearms and Indoor Range, located 32.2km away, where you can find unique gifts and souvenirs.

Recreation

Jacob's Aquatic Center offers a family-friendly atmosphere with refreshing pools, perfect for unwinding. For a touch of luxury, the Key Largo Anglers Club provides exclusive amenities in a picturesque setting. Meanwhile, the New Mahogany Hammock State Botanical Site invites you to relax amidst beautiful flora and tranquil surroundings.

Adventure

The Florida Keys Dive Center offers thrilling underwater sports, located 8.0km from Windley Key, where you can explore vibrant marine life. For adrenaline junkies, Keys Cable Park, 28.0km away, provides an exhilarating adventure activity. Meanwhile, the Pa-hay-okee Trail, also 28.0km away, invites you to hike amidst stunning scenery.

Nightlife

In Windley Key, the nightlife buzzes with excitement at Jimmy Johnson's Big Chill, only 20.9km away, where you can enjoy vibrant entertainment in a romantic setting. The Caribbean Club Bar, located 29.0km away, offers a similar atmosphere, perfect for unwinding with friends and drinks.

Booking tips and Expedia advantages for Windley Key

When planning your visit to Windley Key, consider travelling during the off-peak months from September to November for lower accommodation prices. Booking your hotel about a month in advance can help secure great deals, especially if you choose to stay on a Tuesday, the cheapest day. Explore nearby free attractions like Islamorada County Park and Florida Keys Brewing Co. To maximise savings, use Expedia to find package deals that combine flights, accommodations, and activities, and sort options by price to find the best value for your trip.

  • The most and least expensive months on average to stay in a hotel: The cheapest months to stay around Windley Key are September to November, where the prices are slightly lower. This is in comparison to February to April, where prices are slightly higher.
  • The best time to book a hotel: Book your hotel around Windley Key about 1 month out to secure some of the cheapest prices. If you're the spontaneous type, Expedia's last minute deals and discounts are indicated via the green label below the price.
  • The most and least expensive days on average to stay in a hotel: The least expensive day to stay around Windley Key is Tuesday. The most expensive day to stay around Windley Key is Saturday.
  • Find cheap hotels on Expedia: Utilize Expedia's search tool to refine your choices based on your budget, desired location, and the type of accommodation you prefer. For the best value, be sure to sort the price filter from lowest to highest to uncover the most affordable options and deals available.
  • Consider bundling your trip: You can save some money by combining your Windley Key hotel reservation with your flights and activities through an Expedia package deal.

Find the best attractions near Windley Key

Windley Key is perfect for outdoor enthusiasts and adventure seekers, offering attractions such as Windley Key State Park and the Windley Key Fossil Reef. Visitors can explore notable landmarks and enjoy the natural beauty of urban parks and marinas. With a rich cultural experience awaiting, Windley Key promises an exciting getaway filled with activities that highlight its unique landscape and history.

  • Windley Key Fossil Reef Geological State Park: Experience the incredible geological history of Florida at this unique state park, where you can explore ancient fossilized coral reefs. Enjoy scenic trails surrounded by lush vegetation and discover the rich outdoor vibes that make it perfect for adventurers and nature lovers alike.
  • Founders Park: This vibrant marina offers a beautiful beach and ample opportunities for outdoor adventure. With its stunning views and recreational activities, Founders Park is ideal for those looking to relax by the water or engage in exciting water sports.
  • Islamorada County Park: A fantastic urban park for families, Islamorada County Park features playgrounds, picnic areas, and walking trails. Enjoy the blend of city and outdoor vibes, making it a great spot to unwind and connect with loved ones amidst nature.

Best time to go to Windley Key, Islamorada

The best time to visit Windley Key, Islamorada can depend on the weather and when visitor numbers rise and fall. The hottest average temperature around Windley Key, Islamorada falls in August, when visitor numbers are moderately low and weather is mostly sunny with light rain. The coolest average temperature around Windley Key, Islamorada falls in January, visitor numbers are average and weather is mostly sunny with no rain.

calendar iconCalendar Monthtemperature iconTemperaturerain iconPrecipitationmostly cloudy iconCloudinessoccupation rate iconOccupancyprice iconPricing
January70.0°F (21.1°C)No Rain (Dry)Mostly SunnyAverageAverage
February71.8°F (22.1°C)No Rain (Dry)Mostly SunnyAverageSlightly High
March72.9°F (22.7°C)No Rain (Dry)Mostly SunnyModerately HighSlightly High
April76.6°F (24.8°C)No Rain (Dry)Mostly SunnyAverageSlightly High
May79.3°F (26.3°C)Light RainMostly SunnyAverageAverage
June82.4°F (28.0°C)Light RainMostly SunnyAverageAverage
July83.8°F (28.8°C)Light RainMostly SunnyModerately HighAverage
August84.4°F (29.1°C)Light RainMostly SunnyModerately LowAverage
September83.3°F (28.5°C)Light RainMostly SunnyModerately HighSlightly Low
October80.2°F (26.8°C)Light RainMostly SunnyModerately LowSlightly Low
November75.9°F (24.4°C)Light RainMostly SunnyModerately LowSlightly Low
December72.9°F (22.7°C)No Rain (Dry)Mostly SunnyAverageAverage

The nearest major airports for your trip to Windley Key

To reach Windley Key, you can fly into Marathon, FL (MTH-Florida Keys Marathon), situated 53.1km away. Recommended hotels nearby include the Isla Bella Beach Resort & Spa, a 4.5-star property located 6.4km from the airport, and both the Tranquility Bay Beachfront Hotel and Faro Blanco Resort & Yacht Club Marathon, both rated 4 stars and just 4.8km from MTH. These hotels offer convenient access to the airport, ensuring a smooth transition from your flight to your accommodation. Enjoy the beautiful surroundings of the Florida Keys while staying at these comfortable options.

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