Find hotels in Windley Key, FL from $114

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Our top choices for Windley Key hotels

1. Chesapeake Beach Resort

Chesapeake Beach Resort
3.5 star property
Matecumbe
9.4 out of 10, Exceptional, (1,827 reviews)
"Location is amazing make sure to book a balcony with a view"
United States
Olga Vasiliy
$189 nightly
The price is $213
Nov 16 - Nov 17
Total with taxes and fees
Chesapeake Beach Resort

2. Cheeca Lodge & Spa

Cheeca Lodge & Spa
5.0 star property
Matecumbe
9.2 out of 10, Wonderful, (1,518 reviews)
"Clean room, friendly staff and food was good."
United States
Nicholas
$250 nightly
The price is $281
Nov 16 - Nov 17
Total with taxes and fees
Cheeca Lodge & Spa

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, (314 reviews)
"Great stay!"
United States
Stephen
$272 nightly
The price is $306
Nov 29 - Nov 30
Total with taxes and fees
Three Waters Resort and Marina, Islamorada, a Tribute Portfolio Resort

4. Islander Resort

Islander Resort
4.0 star property
Matecumbe
9.4 out of 10, Exceptional, (1,173 reviews)
"The entire resort was clean, staff very friendly, bar and restaurant and pools were fabulous! Would definitely stay there again!"
United States
DEBORAH
$287 nightly
The price is $323
Nov 29 - Nov 30
Total with taxes and fees
Islander Resort

5. Lime Tree Bay Resort

Lime Tree Bay Resort
3.5 star property
Long Key
9.4 out of 10, Exceptional, (1,599 reviews)
"Great place and great location!"
United States
Donald
$182 nightly
The price is $204
Nov 18 - Nov 19
Total with taxes and fees
Lime Tree Bay Resort

6. Amara Cay Resort

Amara Cay Resort
4.0 star property
Matecumbe
8.8 out of 10, Excellent, (1,332 reviews)
"Great location as well."
United States
Amir
$224 nightly
The price is $252
Nov 18 - Nov 19
Total with taxes and fees
Amara Cay Resort

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

Baker's Cay Resort Key Largo, Curio Collection by Hilton
4.0 star property
Key Largo
8.8 out of 10, Excellent, (1,199 reviews)
"This was an amazing resort. Highly recommend!"
United States
Ryan
$312 nightly
The price is $351
Nov 29 - Nov 30
Total with taxes and fees
Baker's Cay Resort Key Largo, Curio Collection by Hilton

8. Reefhouse Resort & Marina

Reefhouse Resort & Marina
4.5 star property
Key Largo
9.2 out of 10, Wonderful, (1,572 reviews)
"Very nice property, rooms were well appointed, oceanside fire pit was a nice touch."
Canada
Vince
$259 nightly
The price is $286
Nov 29 - Nov 30
Total with taxes and fees
Reefhouse Resort & Marina

9. Fisher Inn Resort & Marina

Fisher Inn Resort & Marina
3.5 star property
Islamorada
8.2 out of 10, Very good, (1,006 reviews)
"We enjoyed everything!"
United States
Susan
$189 nightly
The price is $213
Nov 17 - Nov 18
Total with taxes and fees
Fisher Inn Resort & Marina

10. Hawks Cay Resort

Hawks Cay Resort
4.0 star property
Marathon
8.2 out of 10, Very good, (1,001 reviews)
"Lots of amenities and great staff will be coming back to this location"
United States
Holly
$325 nightly
The price is $364
Dec 9 - Dec 10
Total with taxes and fees
Hawks Cay Resort

11. Coconut Cove Resort and Marina

Coconut Cove Resort and Marina
3.0 star property
Islamorada
9.0 out of 10, Wonderful, (309 reviews)
"Beautiful and quiet place, we will definitely be back in the future!"
United States
Tiffany
$149 nightly
The price is $168
Nov 16 - Nov 17
Total with taxes and fees
Coconut Cove Resort and Marina

12. Playa Largo Resort & Spa, Autograph Collection

Playa Largo Resort & Spa, Autograph Collection
4.5 star property
Rock Harbor
9.0 out of 10, Wonderful, (1,005 reviews)
"Everything was amazing!!! Beautiful hotel and great location."
United States
Jorge
$312 nightly
The price is $351
Nov 29 - Nov 30
Total with taxes and fees
Playa Largo Resort & Spa, Autograph Collection

13. Ocean Pointe Suites at Key Largo

Ocean Pointe Suites at Key Largo
3.5 star property
Tavernier
8.4 out of 10, Very good, (1,002 reviews)
"This was Amazing place to stay and I enjoyed myself I would come again"
United States
Enrique
$152 nightly
The price is $171
Nov 29 - Nov 30
Total with taxes and fees
Ocean Pointe Suites at Key Largo

14. La Siesta Resort & Villas

La Siesta Resort & Villas
4.0 star property
Matecumbe
8.6 out of 10, Excellent, (1,003 reviews)
"Nice place, helpful staff, plenty of places to relax or just hang out."
United States
Mark
$244 nightly
The price is $275
Nov 18 - Nov 19
Total with taxes and fees
La Siesta Resort & Villas

15. Creekside Inn

Creekside Inn
2.5 star property
Tavernier
7.8 out of 10, Good, (1,024 reviews)
"Quite and relaxing place"
United States
MARIO
$132 nightly
The price is $148
Dec 16 - Dec 17
Total with taxes and fees
Creekside Inn

16. Drop Anchor

Drop Anchor
3.0 star property
Islamorada
8.6 out of 10, Excellent, (1,000 reviews)
"They were amazing! Amenities were great fun! Will definitely be back!"
United States
Valerie
$164 nightly
The price is $180
Nov 24 - Nov 25
Total with taxes and fees
Drop Anchor

17. Waterside Suites & Marina

Waterside Suites & Marina
3.5 star property
Key Largo
9.0 out of 10, Wonderful, (1,538 reviews)
"Just a quick stay but was very comfortable."
United States
Bryan
$137 nightly
The price is $154
Nov 18 - Nov 19
Total with taxes and fees
Waterside Suites & Marina

18. The Pelican Key Largo Cottages

The Pelican Key Largo Cottages
2.0 star property
Key Largo
9.0 out of 10, Wonderful, (1,000 reviews)
"Loved the location and the staff were very friendly"
United States
SUSAN
$102 nightly
The price is $115
Dec 2 - Dec 3
Total with taxes and fees
The Pelican Key Largo Cottages

19. Hadley Resort and Marina

Hadley Resort and Marina
3.5 star property
Matecumbe
7.6 out of 10, Good, (1,002 reviews)
"Can’t wait to stay again in the spring. Amazing property."
United States
Jason
$179 nightly
The price is $201
Nov 29 - Nov 30
Total with taxes and fees
Hadley Resort and Marina

20. The Islands of Islamorada

The Islands of Islamorada
5.0 star property
Matecumbe
9.6 out of 10, Exceptional, (83 reviews)
"We had an AMAZING stay! The staff was wonderful, providing excellent customer service and providing local recommendations for activities and dining. The property is pristine and gorgeous. My only critique would be a lack of on property food options. We will definitely be back."
United States
Catherine
$778 nightly
The price is $876
Nov 29 - Nov 30
Total with taxes and fees
The Islands of Islamorada
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.

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.

A colorful building with a sign reading "Florida Keys Brewing Co." and a Santa Claus decoration.

Top Windley Key Hotel Reviews

Find out more about Windley Key

Top reasons to visit Windley Key

  • Stunning Oceanfront Properties: Enjoy beautiful beachfront accommodations perfect for relaxation and adventure.
  • Outdoor Activities: Engage in thrilling dive trips, explore marinas, and visit state parks for family-friendly fun.
  • Cultural Experiences: Discover the rich history at Windley Key Fossil Reef and nearby attractions.
  • Charming Neighborhoods: Stroll through welcoming communities ideal for romantic outings and family adventures.
  • Vibrant Local Scene: Experience music nights and shopping, offering a lively atmosphere for all visitors.

Find great hotels near Windley Key

Discover the charm of Windley Key, Florida, where a variety of hotel accommodations await to enhance your vacation experience. From family-friendly resorts to adventurous hotels, you'll find the perfect spot to unwind and explore the beauty of the Florida Keys. Whether you're seeking thrilling activities, stunning beaches, or a relaxing getaway, Windley Key has the ideal lodging options to make your stay unforgettable.

  • Amara Cay Resort: Amara Cay Resort is a charming 3.5-star property with a guest rating of 8.8, designed for those seeking a beach and adventure getaway. Located 5 miles from Windley Key, this resort offers direct beach access and a plethora of adventure sports, including snorkeling and kayaking right on-site. The pet-friendly atmosphere allows furry friends to join in on the fun, with amenities like food and water bowls provided. With activities such as hiking, biking, and fishing available nearby, guests can enjoy a perfect mix of relaxation and adventure during their stay.
  • Three Waters Resort and Marina, Islamorada, a Tribute Portfolio Resort: With a 3-star rating and a guest rating of 9.0, Three Waters Resort is only 1 mile from Windley Key and ideal for families looking for a beach vacation. This resort features direct access to the beach and a variety of on-site adventure options, including personal watercraft and pedal boating. Family-friendly amenities such as free cribs and an arcade game room ensure that children will have a blast, while parents can unwind knowing their little ones are entertained in a safe environment.
  • Cheeca Lodge & Spa: Cheeca Lodge & Spa boasts a 4-star rating and an impressive guest rating of 9.2, making it a premier choice for travelers seeking a luxurious beach and golf-themed experience. Situated 4 miles from Windley Key, this resort features direct beach access and a renowned golf course. Guests can indulge in a range of activities, from relaxing spa treatments to engaging in a round of golf, all while enjoying stunning views and the tranquil ambiance of the Florida Keys.

Where to stay near Windley Key

Windley Key, nestled near Islamorada, offers an idyllic escape for families and adventurers alike. With its stunning oceanfront and beachfront properties, this island paradise is perfect for relaxed getaways. Explore the charming neighborhoods that boast a welcoming atmosphere, ideal for romantic strolls and fun family outings. Experience the friendly locals and the natural beauty that make Windley Key a must-visit destination for anyone seeking sun, sand, and serenity.

  • Islamorada: Known as the Village of Islands, Islamorada is a picturesque destination that offers stunning views and a laid-back island vibe. Located in the heart of the Florida Keys, it is renowned for its outdoor activities such as fishing, snorkeling, and diving, making it a perfect family getaway. With a peak visitor season from March to April and July, travelers flock to its beautiful beaches and charming tourist precincts. Islamorada features a variety of resorts, shopping areas, and local landmarks, ensuring a delightful experience for everyone.
  • Tavernier: Just 6 miles from Windley Key, Tavernier is another gem in the Florida Keys. This city boasts a vibrant community atmosphere and is known for its family-friendly activities. Travelers appreciate the outdoor experiences available, including beach outings and local shopping centers. Like Islamorada, Tavernier sees peak visitor numbers in March to April and July, offering a range of resorts and attractions. Its proximity to beautiful beaches makes it an ideal spot for relaxation and exploration.
  • Venetian Shores: Located a mere half-mile from Windley Key, Venetian Shores is a tranquil neighborhood that attracts visitors year-round. While it experiences peak traffic from February to March and July, it remains a serene escape for families and beach lovers. This area is famous for its outdoor adventures and underwater sports, making it a favorite for those seeking both relaxation and excitement. With easy access to beautiful beaches and family-friendly activities, Venetian Shores is a charming place to unwind and enjoy the natural beauty of the Florida Keys.

Things to do near Windley Key

Windley Key offers a perfect blend of outdoor and family-friendly activities. Visitors can explore local attractions, enjoy music nights, and embark on exciting dive trips. The area also features shopping malls and recreational spots, making it an ideal starting point for a fun-filled vacation. Whether you're looking to relax on the beach or engage in thrilling adventures, Windley Key has something for everyone.

Shopping

In Windley Key, you can explore local shops and galleries for unique gifts and souvenirs. Don’t miss the nearby Islamorada's shops featuring coastal décor and handcrafted items. For a wider selection, head to the Florida Keys Outlet Marketplace in nearby Key Largo for brand-name bargains.

Recreation

Experience the luxury of Key Largo Anglers Club, a private haven 31 miles from Windley Key. Indulge in upscale amenities while enjoying serene surroundings. Engage in recreational activities like fishing or simply unwind in a tranquil atmosphere, perfect for rejuvenation and relaxation.

Adventure

Explore the Florida Keys National Marine Sanctuary for snorkeling among vibrant coral reefs and marine life. For a thrilling experience, try kayaking through the mangroves, where you can encounter diverse wildlife and enjoy the serene beauty of the natural surroundings.

Nightlife

Experience the vibrant nightlife at the Islander Watersports, where you can enjoy live music and refreshing cocktails by the water. For a laid-back atmosphere, visit the nearby Tiki Bar, offering tropical drinks and a friendly vibe under the stars.

*Distances are measured in a straight line; actual driving distances may vary depending on the route.

Booking tips and Expedia advantages for Windley Key

  • 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: The cheapest time to book a hotel around Windley Key is usually 1 month out from when you are planning to stay. If you're a little more spontaneous, you could also peruse Expedia's last minute deals which could secure you a cheaper stay. Look out for the green banner below the price to spot the deals.
  • 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: Expedia's search tool enables you to set your budget, choose your desired location, and much more. You can organize your results to display prices from lowest to highest, making it easy to find the most affordable hotels first. Additionally, you can refine your search by hotel type—if you check the Eco-certified filter, you'll be shown sustainable and eco-friendly hotel options that you can book.
  • Consider bundling your trip: You can save money by combining your hotel stay at Windley Key with your flights and activities through an Expedia package deal.

Find the best attractions near Windley Key

Windley Key, Florida, is perfect for outdoor and family vacations, offering a variety of attractions such as marinas and state parks. Visitors can enjoy cultural and adventure experiences while exploring nearby sites like the Windley Key Fossil Reef and Long Key. Additionally, there are various rental options available to enhance your stay. Whether you're looking for beach fun or nature exploration, Windley Key has something for everyone.

  • Bud n' Mary's Dive Center: Located 6 miles from Windley Key, this vibrant marina offers thrilling water adventures, including diving and fishing. Immerse yourself in the beautiful waters of the Florida Keys while enjoying the beach and outdoor vibes.
  • Islamorada County Park: Just 2 miles away, this urban park is perfect for families seeking outdoor fun. With its playgrounds, picnic areas, and walking paths, it's a great spot to relax and enjoy the city and nature.
  • Windley Key Fossil Reef Geological State Park: A mere 0.7 miles from Windley Key, this national park showcases stunning scenery and unique geological features. Explore fossilized coral reefs while embracing the adventure and outdoor experience.

Best time to go to Windley Key

The best time to visit Windley Key, Islamorada is dependent on what kind of holiday you are seeking. August is its hottest month on average. At this time, visitor numbers are moderately low and weather is mostly sunny with light rain. January is its coolest month on average. At this time, visitor numbers are average and weather is mostly sunny with no rain.

Calendar MonthTemperaturePrecipitationCloudinessOccupancyPricing
January70.0°F (21.1°C)No RainMostly SunnyAverageAverage
February71.8°F (22.1°C)No RainMostly SunnyAverageSlightly High
March72.9°F (22.7°C)No RainMostly SunnyModerately HighSlightly High
April76.6°F (24.8°C)No RainMostly 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 RainMostly SunnyAverageAverage

The nearest major airports for your trip to Windley Key

Traveling to Windley Key is convenient with several major airports nearby. MIAmi International Airport (MIA) is 61 miles away, with luxurious hotel options like W South Beach and 1 Hotel South Beach, both 9 miles from the airport, and InterContinental Miami, just 6 miles away. Fort Lauderdale-Hollywood International Airport (FLL) is 82 miles from Windley Key, featuring top-rated hotels such as The Ritz-Carlton and Conrad Fort Lauderdale Beach, both 4-5 miles from the airport. Additionally, Key West International Airport (EYW) is located 78 miles away, offering excellent accommodations like Casa Marina Key West and Parrot Key Hotel & Villas, both within 1-2 miles of the airport.

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