Windley Key Vacation Packages 2026 from $491

Windley Key flight + hotel vacation packages

Price found within the past 48 hours. Click for updated prices.

Cavalier Hotel South Beach

South Beach

$491

per person

Jan 17 - Jan 22

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 express check-out are also offered.

Hawks Cay Resort

$1,136

per person

Jan 24 - Jan 31

found 1 day ago

Roundtrip flight included

Boston (BOS) to Miami (MIA)

This luxury hotel features a private beach, a full-service spa, and a marina. Spend a day at the beach snorkeling, or relax with sun loungers and beach umbrellas. There's fun for all ages with a children's club and a children's pool, and families will appreciate the picnic area.

The Retreat Collection at 1 Hotel & Homes South Beach

South Beach

$4,676

per person

Feb 16 - Feb 19

found 1 day ago

Roundtrip flight included

Boston (BOS) 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.

The Shelborne By Proper, a Member of Design Hotels

South Beach

$1,414

per person

Jan 16 - Jan 20

found 1 day ago

Roundtrip flight included

Boston (BOS) to Miami (MIA)

A private beach, a 24-hour gym, and a restaurant are all featured at this boutique hotel. Relax with free beach cabanas and sun loungers, and cool off with a drink at the beachside bar. Relax with a drink at one of the 3 bars/lounges and get perks like free WiFi.

The Penguin Hotel

South Beach

Save 100% on your flight

$637

per person

Mar 4 - Mar 10

found 1 day ago

Roundtrip flight included

Boston (BOS) to Miami (MIA)

This hotel features a restaurant, an outdoor pool, and a bar/lounge. WiFi in public areas is free. 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

84001 Overseas Hwy Islamorada FL

Free Cancellation

Reserve now, pay when you stay

$271 nightly

$304 total

Dec 16 - Dec 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

84951 Overseas Hwy Islamorada FL

Free Cancellation

Reserve now, pay when you stay

$173 nightly

$195 total

Dec 15 - Dec 16

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

84801 Overseas Highway Islamorada FL

$139 nightly

$157 total

Dec 11 - Dec 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

84959 Overseas Highway, 222 Islamorada FL

$184 nightly

$202 total

Jan 4 - Jan 5, 2026

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

Chesapeake Beach Resort

83409 Overseas Hwy Islamorada FL

Free Cancellation

Reserve now, pay when you stay

$208 nightly

$235 total

Dec 11 - Dec 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

Lime Tree Bay Resort

68500 Overseas Hwy Long Key FL

Free Cancellation

Reserve now, pay when you stay

$179 nightly

$201 total

Dec 11 - Dec 12

Total with taxes and fees

This resort features a private beach, 3 outdoor pools, and a restaurant. Business travelers can take advantage of the free WiFi in public areas. Enjoy the outdoor tennis court and perks like free self parking.

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

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.

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.

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 $491. 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.