Windley Key Vacation Packages 2026 from $297

Windley Key flight + hotel vacation packages

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

UMA House by Yurbban South Beach

South Beach

Save 100% on your flight

$297

per person

Aug 21 - Aug 24

found 1 day ago

Roundtrip flight included

Atlanta (ATL) to Miami (MIA)

This hotel features an outdoor pool and a rooftop terrace. Relax with a drink at the poolside bar and enjoy perks like free WiFi. Valet parking, dry cleaning, and luggage storage are also offered.

MirabileCondoDwntown MIA Brickell w PRKG

Downtown Miami

$381

per person

Jul 24 - Jul 26

found 1 day ago

Roundtrip flight included

Atlanta (ATL) to Miami (MIA)

This apartment features a restaurant, an indoor pool, and a bar/lounge. WiFi in public areas is free. Self parking and a coffee shop are also offered on site.

Casablanca Miami Beach

North Beach

$2,432

per person

Jul 23 - Jul 27

found 1 day ago

Roundtrip flight included

Atlanta (ATL) to Miami (MIA)

An outdoor pool, valet parking, and laundry facilities are featured at this aparthotel. A grocery/convenience store, a communal living room, and express check-out are also on offer.

Cavalier Hotel South Beach

South Beach

$377

per person

Aug 13 - Aug 16

found 1 day ago

Roundtrip flight included

Atlanta (ATL) 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.

The Retreat Collection at 1 Hotel & Homes South Beach

South Beach

$7,397

per person

Sep 3 - Sep 7

found 1 day ago

Roundtrip flight included

Atlanta (ATL) 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.

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

$336 nightly

$378 total

Jul 7 - Jul 8

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.

Fisher Inn Resort & Marina

84951 Overseas Hwy Islamorada FL

Free Cancellation

Reserve now, pay when you stay

$188 nightly

$212 total

Jun 15 - Jun 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.

Coconut Cove Resort and Marina

84801 Overseas Highway Islamorada FL

$179 nightly

$201 total

Jun 14 - Jun 15

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.

Drop Anchor

84959 Overseas Highway, 222 Islamorada FL

$160 nightly

$176 total

Jun 15 - Jun 16

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.

Cheeca Lodge & Spa

81801 Overseas Highway, Mile Marker 82 Islamorada FL

Free Cancellation

Reserve now, pay when you stay

$261 nightly

$294 total

Jun 14 - Jun 15

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.

Reefhouse Resort & Marina

103800 Overseas Hwy Key Largo FL

Free Cancellation

Reserve now, pay when you stay

$239 nightly

$264 total

Jun 21 - Jun 22

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.

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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(218 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.

Hog Heaven

After visiting Hog Heaven, make a plan to see the other sights and activities in Islamorada. Discover the beautiful sunsets in this relaxing area, or enjoy its fishing spots.

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 $297. 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.