Deals on vacations and trips to Windley Key

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President Villa

President Villa

3.5 out of 5
South Beach
Price was $1,005, price is now $486 per person
$486
per person
Dec 5 - Dec 8
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Miami (MIA)
This hotel features a restaurant, an outdoor pool, and a bar/lounge. Enjoy the free full breakfast each morning. Valet parking, a terrace, and luggage storage are also offered.
Cavalier Hotel South Beach

Cavalier Hotel South Beach

3.5 out of 5
South Beach
Price was $1,185, price is now $538 per person
$538
per person
Dec 5 - Dec 8
found 1 day ago
Roundtrip flight included
Atlanta (ATL) 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 express check-out are also offered.
Henrosa Hotel

Henrosa Hotel

3.5 out of 5
South Beach
Price was $1,062, price is now $489 per person
$489
per person
Dec 5 - Dec 8
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Miami (MIA)
This hotel features free WiFi in public areas, concierge services, and valet parking. A terrace, a garden, and luggage storage 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 $14,502, price is now $6,929 per person
$6,929
per person
Dec 5 - Dec 8
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Miami (MIA)
This condo resort 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.
Winslow's Bungalows - Key West Historic Inns

Winslow's Bungalows - Key West Historic Inns

4 out of 5
Old Town Key West
Price was $2,383, price is now $1,145 per person
$1,145
per person
Oct 26 - Nov 2
found 1 day ago
Roundtrip non-stop flight included
Atlanta (ATL) to Key West (EYW)
This smoke-free hotel features 3 outdoor pools, a bar/lounge, and a poolside bar. Guests will appreciate free perks like continental breakfast and WiFi in public areas. 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

3.5 out of 5
84001 Overseas Hwy, Islamorada, FL
Free Cancellation
Reserve now, pay when you stay
$220 nightly
The price is $247 total per night
$247 total
Sep 16 - Sep 17
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
$143 nightly
The price is $161 total per night
$161 total
Sep 14 - Sep 15
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
$128 nightly
The price is $145 total per night
$145 total
Sep 11 - Sep 12
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
$151 nightly
The price is $166 total per night
$166 total
Sep 17 - Sep 18
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.
Chesapeake Beach Resort

Chesapeake Beach Resort

3.5 out of 5
83409 Overseas Hwy, Islamorada, FL
Free Cancellation
Reserve now, pay when you stay
$150 nightly
The price is $169 total per night
$169 total
Sep 11 - Sep 12
Total with taxes and fees
A private beach, a marina, and 2 outdoor pools are all featured at this smoke-free hotel. Enjoy a day at the beach kayaking, or relax with sun loungers. Unwind with a drink at the bar/lounge and enjoy perks like free continental breakfast and free WiFi.
On private beach
Pool
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
$177 nightly
The price is $200 total per night
$200 total
Sep 17 - Sep 18
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
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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.

Popular places to visit

Theater of the Sea

Theater of the Sea

Take the kids to visit the sea life you'll find at Theater of the Sea during your trip to Islamorada. Take in the entertainment choices and beautiful sunsets in this family-friendly area.

Theater of the Sea
Windley Key Fossil Reef Geological State Park

Windley Key Fossil Reef Geological State Park

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.

Windley Key Fossil Reef Geological State Park

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 $486. 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

Windley Key Fossil Reef Geological State Park
Windley Key Fossil Reef Geological State Park
Windley Key Fossil Reef Geological State Park
Theater of the Sea
Theater of the Sea