Deals on vacations and trips to Windley Key

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Windley Key flight + hotel vacation packages

Price found within the past 48 hours. Click for updated prices.
Clinton Hotel South Beach

Clinton Hotel South Beach

4 out of 5
South Beach
Save 100% on your flight
Price was $713, price is now $378 per person
$378
per person
Oct 3 - Oct 10
found 1 day ago
Roundtrip flight included
Boston (BOS) to Miami (MIA)
This smoke-free hotel includes 2 restaurants, an outdoor pool, and a gym. A bar/lounge, a 24-hour front desk, and a poolside bar are also provided.
Casablanca Miami Beach

Casablanca Miami Beach

3 out of 5
North Beach
Price was $7,126, price is now $2,807 per person
$2,807
per person
Oct 13 - Oct 16
found 1 day ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Miami (MIA)
An outdoor pool, valet parking, and laundry facilities are featured at this aparthotel. A grocery/convenience store, a communal living room, and express check-out are also on offer.
The Retreat Collection at 1 Hotel & Homes South Beach

The Retreat Collection at 1 Hotel & Homes South Beach

5 out of 5
South Beach
Price was $20,010, price is now $9,633 per person
$9,633
per person
Oct 23 - Oct 28
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Miami (MIA)
This aparthotel features 2 restaurants, 3 outdoor pools, and a gym. There's fun for all ages with a children's club and a children's pool, and babysitting is an added bonus. Enjoy the a rooftop terrace and perks like free WiFi.
The Marlin Hotel

The Marlin Hotel

4 out of 5
South Beach
Save 100% on your flight
Price was $1,168, price is now $619 per person
$619
per person
Oct 5 - Oct 10
found 1 day ago
Roundtrip flight included
Boston (BOS) to Miami (MIA)
A restaurant and a bar/lounge are featured at this hotel. WiFi in public areas is free. Valet parking, a terrace, and a grocery/convenience store are also offered.
Bay Breeze Premium Apartments By Eskape Collection

Bay Breeze Premium Apartments By Eskape Collection

4 out of 5
Save 100% on your flight
Price was $884, price is now $489 per person
$489
per person
Oct 3 - Oct 10
found 1 day ago
Roundtrip flight included
Boston (BOS) to Miami (MIA)
This aparthotel features an outdoor pool and a rooftop terrace. WiFi in public areas is free. Self parking, a garden, and luggage storage are also offered.

Top Windley Key hotels deals

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

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

4 out of 5
84001 Overseas Hwy Islamorada FL
Free Cancellation
Reserve now, pay when you stay
$272 nightly
The price is $306 total per night
$306 total
Aug 10 - Aug 11
Total with taxes and fees
This Art Deco resort features a private beach, a marina, and 4 restaurants. Enjoy a day at the beach snorkeling, or relax with sun loungers. Families will appreciate the arcade/game room and complimentary bicycles.
On private beach
Pool
Fisher Inn Resort & Marina

Fisher Inn Resort & Marina

3.5 out of 5
84951 Overseas Hwy Islamorada FL
Free Cancellation
Reserve now, pay when you stay
$158 nightly
The price is $178 total per night
$178 total
Aug 9 - Aug 10
Total with taxes and fees
A private beach and an outdoor pool are featured at this Art Deco motel. Spend a day at the beach snorkeling, or relax with sun loungers and beach umbrellas. There's no skimping on freebies - guests receive free on-the-go breakfast, free WiFi, and free self parking.
On private beach
Pool
Coconut Cove Resort and Marina

Coconut Cove Resort and Marina

3 out of 5
84801 Overseas Highway Islamorada FL
$149 nightly
The price is $168 total per night
$168 total
Aug 30 - Aug 31
Total with taxes and fees
A marina and an outdoor pool are featured at this hotel. Families will appreciate the children's pool and barbecue grills. Enjoy the gym and free perks like continental breakfast and free self parking.
Pool
Breakfast included
Drop Anchor

Drop Anchor

3 out of 5
84959 Overseas Highway, 222 Islamorada FL
$142 nightly
The price is $155 total per night
$155 total
Aug 3 - Aug 4
Total with taxes and fees
An outdoor pool, free self parking, and barbecue grills are featured at this hotel. WiFi in public areas is free. A business center, a garden, and a picnic area are also on offer.
Pool
Pet friendly
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
$207 nightly
The price is $233 total per night
$233 total
Aug 10 - Aug 11
Total with taxes and fees
This luxury resort features a private beach, a golf course, and a full-service spa. Enjoy beachfront dining and relax with sun loungers and beach umbrellas. There's fun for all ages with a free kid's club and a playground, and families will appreciate the onsite laundry facilities.
On private beach
Pool
Reefhouse Resort & Marina

Reefhouse Resort & Marina

4.5 out of 5
103800 Overseas Hwy Key Largo FL
Free Cancellation
Reserve now, pay when you stay
$259 nightly
The price is $286 total per night
$286 total
Aug 2 - Aug 3
Total with taxes and fees
This luxury hotel features a private beach, a full-service spa, and a marina. Enjoy beachfront dining and relax with sun loungers and beach umbrellas. Family-friendly amenities include an arcade/game room and kid-friendly dining, along with kayaking.
On private beach
Pool
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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.

Stay near popular Windley Key attractions

Windley Key Fossil Reef Geological State Park

8.8/10 (184 reviews)
Explore the great outdoors at Windley Key Fossil Reef Geological State Park and enjoy the beautiful sunsets during your trip to Islamorada. Wander the seaside and beautiful beaches in this family-friendly area.
See properties

Frequently asked questions

How much are vacation packages to Windley Key?
Spoil yourself with a memorable travel experience in Windley Key with a vacation package starting at $378. Booking tours, hotels and flights with Travelocity is simple. On top of that, our great deals will leave you with extra cash for plenty of fun times.
Where can I get the best vacation package deals for Windley Key?
Walking away with a great package deal to Windley Key is a breeze with Travelocity. With access to 400 partner airlines and 1,000,000 properties all over the globe, you'll have loads of choice when selecting your flights and hotels.
Why should I purchase my Windley Key vacation package with Travelocity?
Because you'll never roam alone if you book your trip with us, and we offer 24/7 customer support and high-quality service to boot. Add to that our Price Match Guarantee and countless experiences and destinations to select from. We're here to help you have the trip of a lifetime.
Will I save money on my Windley Key car rental if I book it with a hotel or flight?
You certainly can with our Windley Key vacation packages. With one of these, there are tons of ways to stretch your travel budget further. Combine any two or more car, flight, hotel and tour bookings and watch the savings start to pile up. With a rental car, all the landmarks in and around Windley Key are a memorable road trip away.

Photos of local treasures

Browse Windley Key vacation photos for more inspiration

A colorful building with a sign reading "Florida Keys Brewing Co." and a Santa Claus decoration.
A forest path surrounded by dense green foliage and trees.
A rocky cliff with intricate erosion patterns and a small cave entrance.
A close-up of a palm plant with long, green leaves against a rocky background.
A forest path surrounded by trees and foliage.

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