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, Marker 82, Islamorada, FL
Free Cancellation
Reserve now, pay when you stay
$199 nightly
The price is $224 total per night
$224 total
Oct 26 - Oct 27
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, luggage storage, and securing valuables. Other amenities at this beach resort include 3 outdoor pools, a 24-hour gym, and a sauna.
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
Free Cancellation
Reserve now, pay when you stay
$337 nightly
The price is $379 total per night
$379 total
Oct 27 - Oct 28
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. Parking is available for USD 11.20 per night (USD 16.80 per night for valet parking), and there's also limo/town car service. The front desk has multilingual staff on hand 24/7 to help with dry cleaning/laundry, securing valuables, 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 hot tub, a conference center, and a 24-hour business center.
On private beach
Pool
Amara Cay Resort

Amara Cay Resort

4 out of 5
80001 Overseas Hwy, Islamorada, FL
Free Cancellation
Reserve now, pay when you stay
$208 nightly
The price is $234 total per night
$234 total
Oct 26 - Oct 27
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
Playa Largo Resort & Spa, Autograph Collection

Playa Largo Resort & Spa, Autograph Collection

4.5 out of 5
97450 Overseas Highway, Key Largo, FL
Free Cancellation
Reserve now, pay when you stay
$288 nightly
The price is $324 total per night
$324 total
Oct 27 - Oct 28
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 37.63 per night. Multilingual staff at the 24-hour front desk can assist with access to locker space, 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 and an off-leash area. 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
$245 nightly
The price is $276 total per night
$276 total
Oct 27 - Oct 28
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
Lime Tree Bay Resort

Lime Tree Bay Resort

3.5 out of 5
68500 Overseas Hwy, Long Key, FL
Free Cancellation
Reserve now, pay when you stay
$149 nightly
The price is $168 total per night
$168 total
Nov 9 - Nov 10
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
La Siesta Resort & Villas

La Siesta Resort & Villas

4 out of 5
80241 Overseas Highway, Islamorada, FL
Free Cancellation
Reserve now, pay when you stay
$193 nightly
The price is $217 total per night
$217 total
Oct 30 - Oct 31
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. 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, a water dispenser, and wedding services.
On private beach
Pool
Matecumbe Resort

Matecumbe Resort

2 out of 5
76261 Overseas Hwy, Islamorada, FL
Free Cancellation
Reserve now, pay when you stay
$125 nightly
The price is $141 total per night
$141 total
Oct 22 - Oct 23
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 garden.
On private beach
Pool
2 BD/2BA VILLA WITH BOAT SLIP IN ISLAMORADA,FL

2 BD/2BA VILLA WITH BOAT SLIP IN ISLAMORADA,FL

Guests staying at this resort enjoy a hot tub, laundry facilities, and barbecue grills.
Pool
Hot Tub
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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
    $245 nightly
    The price is $276 total per night from Oct 27 to Oct 28
    $276 total
    Oct 27 - Oct 28
    Total with taxes and fees
    8.8/10 Excellent! (97 reviews)
    Fisher Inn Resort & Marina

    Fisher Inn Resort & Marina

    84951 Overseas Hwy, Islamorada, FL
    $139 nightly
    The price is $156 total per night from Oct 21 to Oct 22
    $156 total
    Oct 21 - Oct 22
    Total with taxes and fees
    8/10 Very Good! (1,006 reviews)
    Coconut Cove Resort and Marina

    Coconut Cove Resort and Marina

    84801 Overseas Highway, Islamorada, FL
    $149 nightly
    The price is $168 total per night from Oct 21 to Oct 22
    $168 total
    Oct 21 - Oct 22
    Total with taxes and fees
    7.6/10 Good! (825 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
$141
Highest Price
$379
Popular accommodation
Cheeca Lodge & Spa, Baker's Cay Resort Key Largo, Curio Collection by Hilton, Amara Cay Resort, Playa Largo Resort & Spa, Autograph Collection, Three Waters Resort and Marina, Islamorada, a Tribute Portfolio Resort, Lime Tree Bay Resort, La Siesta Resort & Villas, Matecumbe Resort, 2 BD/2BA VILLA WITH BOAT SLIP IN ISLAMORADA,FL

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