Windley Key Vacation Packages 2025/2026 from $425

Name: Drop Anchor
Price range: $142 total

Windley Key flight + hotel vacation packages

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

Flow Miami Hotel

Downtown Miami

Save 100% on your flight

$425

per person

Jan 10 - Jan 14

found 1 day ago

Roundtrip flight included

Boston (BOS) to Miami (MIA)

This apartment features an outdoor pool and a 24-hour gym. WiFi in public areas is free. Valet parking and a safe deposit box are also offered on site.

The Retreat Collection at 1 Hotel & Homes South Beach

South Beach

$20,515

per person

Dec 26 - Jan 2

found 1 day ago

Roundtrip non-stop 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.

Bahama Beach Club Pompano

$628

per person

Jan 1 - Jan 8

found 1 day ago

Roundtrip non-stop flight included

Boston (BOS) to Miami (MIA)

This aparthotel doesn't skimp on freebies - guests receive free WiFi and free self parking. If you want to take your pet along, this pet-friendly property offers everything you'll need for your pet including food and water bowls and litter boxes. Enjoy the outdoor pool and conveniences like a garden and barbecue grills.

Hotel Riu Plaza Miami Beach

Mid Beach

Save 100% on your flight

$745

per person

Dec 7 - Dec 14

found 1 day ago

Roundtrip flight included

Boston (BOS) to Miami (MIA)

This hotel features a restaurant, an outdoor pool, and a bar/lounge. Enjoy the gym and perks like free WiFi. There's a poolside bar on site, and a 24-hour front desk and concierge services are also provided.

Beach Place Hotel

North Beach

Save 100% on your flight

$464

per person

Dec 3 - Dec 9

found 1 day ago

Roundtrip flight included

Boston (BOS) to Miami (MIA)

An outdoor pool, free self parking, and laundry facilities are featured at this hotel. There's a garden and multilingual staff can provide around-the-clock assistance.

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

$245 nightly

$276 total

Oct 27 - Oct 28

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

$139 nightly

$156 total

Oct 19 - Oct 20

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

$155 nightly

$175 total

Oct 29 - Oct 30

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

$130 nightly

$142 total

Oct 21 - Oct 22

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

81801 Overseas Highway, Mile Marker 82, Marker 82, Islamorada, FL

Free Cancellation

Reserve now, pay when you stay

$199 nightly

$224 total

Oct 26 - Oct 27

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

Baker's Cay Resort Key Largo, Curio Collection by Hilton

97000 Overseas Hwy, Key Largo, FL

Free Cancellation

Reserve now, pay when you stay

$354 nightly

$398 total

Oct 26 - Oct 27

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.

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 $425. 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.