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.
The Local House

The Local House

3.5 out of 5
South Beach
Save 100% on your flight
Price was $983, price is now $526 per person
$526
per person
Oct 1 - Oct 5
found 2 hours ago
Roundtrip flight included
Atlanta (ATL) to Miami (MIA)
This hotel features a restaurant, an outdoor pool, and a bar/lounge. Enjoy the a rooftop terrace and perks like free WiFi. A poolside bar, a coffee shop, and a terrace are also provided.
Casablanca Miami Beach

Casablanca Miami Beach

3 out of 5
North Beach
Price was $1,791, price is now $869 per person
$869
per person
Sep 24 - Sep 28
found 1 day ago
Roundtrip flight included
New York (JFK) 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.
Bay Breeze Premium Apartments By Eskape Collection

Bay Breeze Premium Apartments By Eskape Collection

4 out of 5
Price was $1,121, price is now $548 per person
$548
per person
Oct 14 - Oct 20
found 11 hours ago
Roundtrip flight included
Atlanta (ATL) 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.
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 $15,540, price is now $8,068 per person
$8,068
per person
Sep 24 - Sep 28
found 1 day ago
Roundtrip flight included
Atlanta (ATL) 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.
Nobu Hotel Miami Beach

Nobu Hotel Miami Beach

5 out of 5
Mid Beach
Save 100% on your flight
Price was $1,170, price is now $608 per person
$608
per person
Oct 8 - Oct 12
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Miami (MIA)
A full-service spa, 2 restaurants, and 4 outdoor pools are all featured at this smoke-free resort. Relax with a drink at one of the 2 bars/lounges and get perks like free WiFi. You'll appreciate the gym, poolside bar, and concierge services.

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.
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
$168 nightly
The price is $189 total per night
$189 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
$189 nightly
The price is $213 total per night
$213 total
Jul 23 - Jul 24
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.
Drop Anchor

Drop Anchor

3 out of 5
84959 Overseas Highway, 222 Islamorada FL
$190 nightly
The price is $209 total per night
$209 total
Jul 23 - Jul 24
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.
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
$226 nightly
The price is $254 total per night
$254 total
Aug 2 - Aug 3
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.
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
$302 nightly
The price is $340 total per night
$340 total
Aug 17 - Aug 18
Total with taxes and fees
A private beach, 2 restaurants, and 2 outdoor pools are all featured at this resort. Enjoy beachfront dining and relax with sun loungers and beach umbrellas. Families will appreciate the arcade/game room and complimentary bicycles.
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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 $526. 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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