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.
Sea View Hotel, Bal Harbour, On The Ocean

Sea View Hotel, Bal Harbour, On The Ocean

3.5 out of 5
Save 100% on your flight
Price was $1,088, price is now $622 per person
$622
per person
Oct 24 - Oct 31
found 1 day ago
Roundtrip non-stop flight included
Detroit (DTW) to Miami (MIA)
This hotel features an outdoor pool, a gym, and a restaurant. Enjoy beachfront dining and relax with beach cabanas and sun loungers. Relax with a drink at the bar/lounge and enjoy perks like free WiFi.
Park Royal Miami Beach managed by Accor

Park Royal Miami Beach managed by Accor

2.5 out of 5
North Beach
Price was $1,379, price is now $632 per person
$632
per person
Oct 18 - Oct 24
found 1 day ago
Roundtrip flight included
Detroit (DTW) to Miami (MIA)
An outdoor pool, self parking, and laundry facilities are featured at this hotel. A terrace, a garden, and concierge services 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 $12,043, price is now $6,294 per person
$6,294
per person
Oct 5 - Oct 9
found 19 hours ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) 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.
Bentley Hotel South Beach

Bentley Hotel South Beach

4 out of 5
South Beach
Price was $2,254, price is now $1,220 per person
$1,220
per person
Oct 24 - Oct 31
found 1 day ago
Roundtrip non-stop flight included
Detroit (DTW) to Miami (MIA)
This hotel features an outdoor pool and a rooftop terrace. Enjoy the hot tub and perks like free WiFi. There's a poolside bar on site, and a 24-hour front desk and concierge services are also provided.
President Hotel

President Hotel

3.5 out of 5
South Beach
Save 100% on your flight
Price was $1,240, price is now $717 per person
$717
per person
Nov 7 - Nov 13
found 1 day ago
Roundtrip flight included
Detroit (DTW) to Miami (MIA)
This hotel features an outdoor pool and a bar/lounge. Guests will appreciate free perks like full breakfast and WiFi in public areas. Valet parking, a terrace, and a garden 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
$248 nightly
The price is $279 total per night
$279 total
Sep 10 - Sep 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
$156 nightly
The price is $175 total per night
$175 total
Sep 21 - Sep 22
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
$122 nightly
The price is $137 total per night
$137 total
Oct 5 - Oct 6
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
$233 nightly
The price is $258 total per night
$258 total
Sep 7 - Sep 8
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
$214 nightly
The price is $241 total per night
$241 total
Sep 9 - Sep 10
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
Sep 7 - Sep 8
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 $622. 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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