Windley Key Vacation Packages 2025 from $292

Windley Key flight + hotel vacation packages

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

Henrosa Hotel

South Beach

Save 100% on your flight

per person

Jul 13 - Jul 18

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.

Cavalier Hotel South Beach

South Beach

Save 100% on your flight

per person

Jul 13 - Jul 18

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.

The Retreat Collection at 1 Hotel & Homes South Beach

South Beach

per person

Aug 15 - Aug 18

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.

Fontainebleau Miami Beach

Mid Beach

per person

Jul 13 - Jul 18

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.

Miami accommodations BeachFront

South Beach

Save 100% on your flight

per person

Jul 13 - Jul 18

found 1 day ago

Roundtrip flight included

Atlanta (ATL) to Miami (MIA)

This hotel includes a communal living room and a virtual front desk.

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

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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.

Fisher Inn Resort & Marina

84951 Overseas Hwy, Islamorada, FL

Free Cancellation

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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.

Coconut Cove Resort and Marina

84801 Overseas Highway, Islamorada, FL

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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.

Drop Anchor

84959 Overseas Highway, 222, Islamorada, FL

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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.

Reefhouse Resort & Marina

103800 Overseas Hwy, Key Largo, FL

Free Cancellation

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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.

Cheeca Lodge & Spa

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

Free Cancellation

Reserve now, pay when you stay

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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.

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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 $292. 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.