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.
President Villa

President Villa

3.5 out of 5
South Beach
Save 100% on your flight
per person
Jul 24 - Jul 28
found 7 hours ago
Roundtrip flight included
Atlanta (ATL) to Miami (MIA)
This hotel features a restaurant, an outdoor pool, and a bar/lounge. Enjoy the free buffet 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
per person
Jul 31 - Aug 3
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Miami (MIA)
A restaurant and a bar/lounge are featured at this hotel. Valet parking, a terrace, and express check-out are also offered.
Casablanca Miami Beach

Casablanca Miami Beach

3 out of 5
North Beach
Save 100% on your flight
per person
Jul 24 - Jul 28
found 7 hours ago
Roundtrip flight included
Atlanta (ATL) to Miami (MIA)
An outdoor pool, valet parking, and laundry facilities are featured at this aparthotel. WiFi in public areas is free. A grocery/convenience store, a communal living room, and express check-out are also on offer.
Eden Roc Miami Beach

Eden Roc Miami Beach

4.5 out of 5
Mid Beach
Save 100% on your flight
per person
Jun 9 - Jun 13
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Miami (MIA)
A full-service spa, 2 restaurants, and 3 outdoor pools are all featured at this luxury resort. Enjoy the gym and unwind at the bar/lounge and poolside bar.
Fontainebleau Miami Beach

Fontainebleau Miami Beach

4.5 out of 5
Mid Beach
Save 100% on your flight
per person
Jun 9 - Jun 13
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Miami (MIA)
This luxury hotel features a full-service spa, a nightclub, and 9 restaurants. Families will appreciate the children's pool, onsite laundry facilities, and babysitting. Enjoy the 3 outdoor pools and perks like free WiFi.

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
The price is $352 per night
$352
includes taxes & fees
$313 per night
Jun 1 - Jun 2
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
The price is $239 per night
$239
includes taxes & fees
$213 per night
May 21 - May 22
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

2.5 out of 5
84801 Overseas Highway, Islamorada, FL
The price is $190 per night
$190
includes taxes & fees
$169 per night
May 8 - May 9
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
Reefhouse Resort & Marina

Reefhouse Resort & Marina

3.5 out of 5
103800 Overseas Hwy, Key Largo, FL
Free Cancellation
Reserve now, pay when you stay
The price is $320 per night
$320
includes taxes & fees
$289 per night
Jun 2 - Jun 3
This smoke-free 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
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
The price is $369 per night
$369
includes taxes & fees
$328 per night
May 20 - May 21
This luxury resort features a full-service spa, a marina, and 3 restaurants. Enjoy beachfront dining and relax with beach cabanas and sun loungers. Enjoy the outdoor pool and perks like free WiFi.
Pool
Hot Tub
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
The price is $388 per night
$388
includes taxes & fees
$345 per night
May 19 - May 20
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.
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

4.5/5(215 reviews)

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

4.5/5(20 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.

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 $424. 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