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Find hotels in Windley Key, FL from $110

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Our top choices for Windley Key hotels

1. Chesapeake Beach Resort

Chesapeake Beach Resort
Matecumbe
Guest highlights
  • Beautiful ocean view from room
  • Two clean pools on-site
  • Complimentary breakfast with omelettes
$187 nightly
$210 total
Oct 18 - Oct 19
Total with taxes and fees
Chesapeake Beach Resort

2. Cheeca Lodge & Spa

Cheeca Lodge & Spa
Matecumbe
Guest highlights
  • Gorgeous views from the patio
  • Large pool with poolside service
  • Screened patio for dining
$190 nightly
$214 total
Oct 4 - Oct 5
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
Islamorada
Guest highlights
  • Stunning ocean view from rooms
  • Clean pools with plenty of variety
  • Great food options at on-site restaurant
$280 nightly
$315 total
Oct 18 - Oct 19
Total with taxes and fees
Three Waters Resort and Marina, Islamorada, a Tribute Portfolio Resort

4. Islander Resort

Islander Resort
Matecumbe
Guest highlights
  • Beautiful sunset views from the patio
  • Swimming pool available on site
  • Lovely breakfast each morning
$332 nightly
$374 total
Oct 21 - Oct 22
Total with taxes and fees
Islander Resort

5. Lime Tree Bay Resort

Lime Tree Bay Resort
Long Key
Guest highlights
  • Beautiful sunset views from the balcony
  • Swimming pool on the property
  • Delicious food and dining on offer
$172 nightly
$194 total
Oct 4 - Oct 5
Total with taxes and fees
Lime Tree Bay Resort

6. Amara Cay Resort

Amara Cay Resort
Matecumbe
Guest highlights
  • Beautiful pool area with lounge chairs
  • Very good food at the tiki bar
  • Beautiful ocean view at sunrise
$209 nightly
$235 total
Oct 18 - Oct 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
Key Largo
Guest highlights
  • Stunning beach view from balcony
  • Responsive staff on hand each day
  • Adult pool just a short walk away
$327 nightly
$368 total
Oct 12 - Oct 13
Total with taxes and fees
Baker's Cay Resort Key Largo, Curio Collection by Hilton

8. Reefhouse Resort & Marina

Reefhouse Resort & Marina
Key Largo
Guest highlights
  • Beautiful ocean view from balcony
  • Great pool area with bar
  • Wonderful breakfast to start the day
$259 nightly
$286 total
Oct 4 - Oct 5
Total with taxes and fees
Reefhouse Resort & Marina

9. Fisher Inn Resort & Marina

Fisher Inn Resort & Marina
Islamorada
Guest highlights
  • Views of the ocean from balcony
  • Picnic tables and adirondack chairs
  • Clean and relaxing pool area
$164 nightly
$185 total
Oct 12 - Oct 13
Total with taxes and fees
Fisher Inn Resort & Marina

10. Hawks Cay Resort

Hawks Cay Resort
Marathon
Guest highlights
  • Beautiful view from water view king studio
  • Large main pool with plenty of space
  • Great food options at on-site restaurant
$255 nightly
$286 total
Oct 8 - Oct 9
Total with taxes and fees
Hawks Cay Resort

11. Coconut Cove Resort and Marina

Coconut Cove Resort and Marina
Islamorada
Guest highlights
  • Picturesque pool with waterfall
  • Continental breakfast with yogurt
  • Picturesque view of the ocean
$133 nightly
$149 total
Oct 27 - Oct 28
Total with taxes and fees
Coconut Cove Resort and Marina

12. Playa Largo Resort & Spa, Autograph Collection

Playa Largo Resort & Spa, Autograph Collection
Rock Harbor
Guest highlights
  • Beautiful beach just steps away
  • Excellent food quality at on-site restaurant
  • Lovely pool area with Sun loungers
$312 nightly
$351 total
Oct 15 - Oct 16
Total with taxes and fees
Playa Largo Resort & Spa, Autograph Collection

13. Ocean Pointe Suites at Key Largo

Ocean Pointe Suites at Key Largo
Tavernier
Guest highlights
  • Beautiful ocean view from rooms
  • Clean pool area with bar
  • Great on-site restaurant with food
$150 nightly
$169 total
Oct 8 - Oct 9
Total with taxes and fees
Ocean Pointe Suites at Key Largo

14. La Siesta Resort & Villas

La Siesta Resort & Villas
Matecumbe
Guest highlights
  • Excellent breakfast each morning
  • Pool with spacious area
  • Great location near scenic views
$252 nightly
$283 total
Nov 1 - Nov 2
Total with taxes and fees
La Siesta Resort & Villas

15. Creekside Inn

Creekside Inn
Tavernier
Guest highlights
  • Canal view from the balcony
  • Very nice swimming pools
  • Easy parking on the property
$159 nightly
$179 total
Oct 4 - Oct 5
Total with taxes and fees
Creekside Inn

16. Drop Anchor

Drop Anchor
Islamorada
Guest highlights
  • Beautiful views of the water
  • Balcony overlooking the grounds
  • Large pool area available
$167 nightly
$183 total
Oct 7 - Oct 8
Total with taxes and fees
Drop Anchor

17. Waterside Suites & Marina

Waterside Suites & Marina
Key Largo
Guest highlights
  • Clean kitchen for self-catering
  • Exceptional dining at sharkeys
  • Clean and nice pool area
$135 nightly
$151 total
Nov 1 - Nov 2
Total with taxes and fees
Waterside Suites & Marina

18. The Pelican Key Largo Cottages

The Pelican Key Largo Cottages
Key Largo
Guest highlights
  • Beautiful location near the beach
  • Free and easily accessible parking
$97 nightly
$110 total
Oct 4 - Oct 5
Total with taxes and fees
The Pelican Key Largo Cottages

19. Hadley Resort and Marina

Hadley Resort and Marina
Matecumbe
Guest highlights
  • Beautiful ocean view from rooms
  • Nice and simple pool area
  • Great grab-and-go breakfast options
$164 nightly
$185 total
Oct 18 - Oct 19
Total with taxes and fees
Hadley Resort and Marina

20. The Islands of Islamorada

The Islands of Islamorada
Matecumbe
$534 nightly
$600 total
Oct 14 - Oct 15
Total with taxes and fees
The Islands of Islamorada
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Stay near popular Windley Key attractions

Windley Key Fossil Reef Geological State Park

8.8/10 (184 reviews)
Explore the fossilized reef of a former quarry in this island park, as you learn about the history and ecology from the interpretive trails.
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Hog Heaven

After visiting Hog Heaven, make a plan to see the other sights and activities in Islamorada. Discover the beautiful sunsets in this relaxing area, or enjoy its fishing spots.
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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.

See all hotels in Windley Key
A colorful building with a sign reading "Florida Keys Brewing Co." and a Santa Claus decoration.

Top Windley Key Hotel Reviews

Reefhouse Resort & Marina

Reefhouse Resort & Marina

10/10 Excellent
"Nice property. Disappointed we could not check in earlier."
Marcus B. 2-night trip
Posted 1 hour ago
Reefhouse Resort & Marina
Sunset Cove Beach Resort

Sunset Cove Beach Resort

10/10 Excellent
"Great place"
Frank 1-night trip
Posted 3 hours ago
Sunset Cove Beach Resort
Bayside Inn Key Largo

Bayside Inn Key Largo

10/10 Excellent
"Always my to go place in the Keys! Very friendly staff. Clean rooms."
Lisandra 2-night trip
Posted 9 hours ago
Bayside Inn Key Largo
Hampton Inn Key Largo Manatee Bay

Hampton Inn Key Largo Manatee Bay

10/10 Excellent
"Great stay. Will stay there again"
Tim 1-night trip
Posted 10 hours ago
Hampton Inn Key Largo Manatee Bay
Cheeca Lodge & Spa

Cheeca Lodge & Spa

8/10 Good
"The room was a little loud from the A/C unit but great stay"
Benjamin 2-night trip
Posted 15 hours ago
Cheeca Lodge & Spa
Rock Reef Resort

Rock Reef Resort

10/10 Excellent
"Love evrything"
Monica 1-night trip
Posted 19 hours ago
Rock Reef Resort
Chesapeake Beach Resort

Chesapeake Beach Resort

10/10 Excellent
"Great place"
Juan 4-night trip
Posted 20 hours ago
Chesapeake Beach Resort
Lime Tree Bay Resort

Lime Tree Bay Resort

10/10 Excellent
"Beautiful location, great amenities, and comfortable rooms"
Michael 7-night trip
Posted 2 days ago
Lime Tree Bay Resort
Islander Resort

Islander Resort

10/10 Excellent
"It great amenities but pools are small."
Jaily 2-night trip
Posted 2 days ago
Islander Resort

More cheap stays in Windley Key

The Pelican Key Largo Cottages

The Pelican Key Largo Cottages

99340 Overseas Highway Key Largo FL
$97 nightly
$110 total
Oct 4 - Oct 5
Total with taxes and fees
The Pelican Key Largo Cottages
Rock Reef Resort

Rock Reef Resort

97850 Overseas Hwy Key Largo FL
$101 nightly
$114 total
Oct 4 - Oct 5
Total with taxes and fees
9.2/10 Wonderful! (1,193 reviews)
Rock Reef Resort
Breezy Palms Resort

Breezy Palms Resort

80015 Overseas Highway Islamorada FL
$107 nightly
$120 total
Oct 4 - Oct 5
Total with taxes and fees
Breezy Palms Resort
Hampton Inn Key Largo Manatee Bay

Hampton Inn Key Largo Manatee Bay

102400 Overseas Hwy Key Largo FL
$116 nightly
$131 total
Oct 15 - Oct 16
Total with taxes and fees
8.8/10 Excellent! (1,101 reviews)
Hampton Inn Key Largo Manatee Bay
Sunset Cove Beach Resort

Sunset Cove Beach Resort

MM 99.5 Key Largo FL
$130 nightly
$146 total
Oct 12 - Oct 13
Total with taxes and fees
9.2/10 Wonderful! (1,013 reviews)
Sunset Cove Beach Resort
Creekside Inn

Creekside Inn

90611 Old Highway Tavernier FL
$159 nightly
$179 total
Oct 4 - Oct 5
Total with taxes and fees
7.8/10 Good! (1,021 reviews)
Creekside Inn

Hotels in Windley Key with star-rating

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.

calendarCalendar MonthtemperatureTemperaturerainPrecipitationmostlyCloudinessoccupationOccupancypricePricing
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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