Compare Windley Key Resorts

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Featured Resorts in Windley Key

Cheeca Lodge & Spa

Cheeca Lodge & Spa

5 out of 5
81801 Overseas Highway, Mile Marker 82 Islamorada FL
Free Cancellation
Reserve now, pay when you stay
$257 nightly
The price is $290 total per night
$290 total
Dec 18 - Dec 19
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 concierge services, securing valuables, and luggage storage. Other amenities at this beach resort include 3 outdoor pools, a 24-hour gym, and a sauna.
On private beach
Pool
Lime Tree Bay Resort

Lime Tree Bay Resort

3.5 out of 5
68500 Overseas Hwy Long Key FL
$171 nightly
The price is $193 total per night
$193 total
Dec 17 - Dec 18
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
Amara Cay Resort

Amara Cay Resort

4 out of 5
80001 Overseas Hwy Islamorada FL
$228 nightly
The price is $257 total per night
$257 total
Dec 18 - Dec 19
Total with taxes and fees
At Amara Cay Resort, guests enjoy a private beach, an outdoor pool, and a gym. The 24-hour front desk has multilingual staff ready to help with luggage storage, and answer any questions about the area. 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 meeting room, a terrace, and laundry facilities.
On private beach
Pool
Baker's Cay Resort Key Largo, Curio Collection by Hilton

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

4 out of 5
97000 Overseas Hwy Key Largo FL
$306 nightly
The price is $344 total per night
$344 total
Dec 18 - Dec 19
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. Valet parking is available for USD 35 per night, and there's also limo/town car service. The front desk has multilingual staff on hand 24/7 to help with securing valuables, concierge services, and dry cleaning/laundry. 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
Playa Largo Resort & Spa, Autograph Collection

Playa Largo Resort & Spa, Autograph Collection

4.5 out of 5
97450 Overseas Highway Key Largo FL
$378 nightly
The price is $425 total per night
$425 total
Dec 17 - Dec 18
Total with taxes and fees
Guests of Playa Largo Resort & Spa, Autograph Collection have access to a marina, a full-service spa, and an outdoor pool. Valet parking is offered for USD 39.38 per night. Multilingual staff at the 24-hour front desk can assist with access to locker space, luggage storage, 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 24-hour gym, free WiFi in public areas, and a hot tub.
Pool
Hot Tub
Three Waters Resort and Marina, Islamorada, a Tribute Portfolio Resort

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

3.5 out of 5
84001 Overseas Hwy Islamorada FL
Free Cancellation
Reserve now, pay when you stay
$298 nightly
The price is $335 total per night
$335 total
Dec 17 - Dec 18
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
La Siesta Resort & Villas

La Siesta Resort & Villas

4 out of 5
80241 Overseas Highway Islamorada FL
$328 nightly
The price is $369 total per night
$369 total
Dec 23 - Dec 24
Total with taxes and fees
Guests of La Siesta Resort & Villas have access to a private beach, a marina, and an outdoor pool. Transportation is made easy with a free area shuttle. The 24-hour front desk has staff always at the ready. 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 terrace, wedding services, and a picnic area.
On private beach
Pool
Matecumbe Resort

Matecumbe Resort

2 out of 5
76261 Overseas Hwy Islamorada FL
$156 nightly
The price is $176 total per night
$176 total
Jan 14 - Jan 15, 2026
Total with taxes and fees
Guests staying at Matecumbe Resort enjoy access to a private beach, an outdoor pool, and free WiFi in public areas. You can put free parking to good use if you drive. Friendly staff can provide front-desk service during limited hours, and also offer advice about sightseeing. Other amenities at this beach resort include free use of bicycles, laundry facilities, and a picnic area.
On private beach
Pool
2 Bedrm / 2 Bath Private Beach Boat Dock Fishing Pier Pool Hot Tub Dream Vacay

2 Bedrm / 2 Bath Private Beach Boat Dock Fishing Pier Pool Hot Tub Dream Vacay

Islamorada FL
At this resort, guests have access to features like laundry facilities.
Air conditioning
Laundry
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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.

Hotel Options in Windley Key

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

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

    84001 Overseas Hwy Islamorada FL
    $298 nightly
    The price is $335 total per night from Dec 17 to Dec 18
    $335 total
    Dec 17 - Dec 18
    Total with taxes and fees
    9/10 Wonderful! (115 reviews)
    Fisher Inn Resort & Marina

    Fisher Inn Resort & Marina

    84951 Overseas Hwy Islamorada FL
    $143 nightly
    The price is $160 total per night from Dec 18 to Dec 19
    $160 total
    Dec 18 - Dec 19
    Total with taxes and fees
    8/10 Very Good! (1,002 reviews)
    Coconut Cove Resort and Marina

    Coconut Cove Resort and Marina

    84801 Overseas Highway Islamorada FL
    $146 nightly
    The price is $165 total per night from Dec 17 to Dec 18
    $165 total
    Dec 17 - Dec 18
    Total with taxes and fees
    8.8/10 Excellent! (149 reviews)

Resort Hotels

Resort hotels in Windley Key
Find your next great getaway when you book at a resort hotel in Windley Key. Resorts are great for families or couples, or even solo travelers looking for a piece of paradise. Sure, you can leave your hotel and explore Windley Key at your leisure…but with everything these sorts of hotels offer, you may never want to. From food and shopping to entertainment and organized tours, a resort hotel in Windley Key is a great way to score an amazing vacation—and Orbitz can help you get there.

Resort hotels for everyone in Windley Key
If you’re traveling with the kids, you know how hard it is to keep them entertained. Let them have some fun on their own: some resorts have clubs for the kiddos, including kid-friendly pools and adventure camps where they can explore, do some crafts and even take part in learning activities. (Don’t worry, no one will tell them this vacation is actually educational.) Of course, there’s plenty for adults to do at Windley Key resorts as well. Take a yoga class, book a few treatments at the spa, or do a little shopping. Go ahead, charge it to the room. You’re on vacation!

Ready to wow your special someone? Plan a romantic getaway complete with luxury accommodations. Surprise your partner with a couples massage, followed by a candlelit dinner at the 5-star on-site hotel. Some of these luxury hotels even have adults-only pools with swim-up bars so you can float about with a couple of cocktails, watching the sunset and enjoying your time together.

Windley Key Resorts essential information

Accommodation
14 Resorts
Lowest Price
$160
Highest Price
$425
Popular accommodation
Cheeca Lodge & Spa, Lime Tree Bay Resort, Amara Cay Resort, Baker's Cay Resort Key Largo, Curio Collection by Hilton, Playa Largo Resort & Spa, Autograph Collection, Three Waters Resort and Marina, Islamorada, a Tribute Portfolio Resort, La Siesta Resort & Villas, Matecumbe Resort, 2 Bedrm / 2 Bath Private Beach Boat Dock Fishing Pier Pool Hot Tub Dream Vacay

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