Windley Key Vacation Packages 2026 from $497

Windley Key flight + hotel vacation packages

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

Seacoast Suites on Miami Beach

Mid Beach

Save 100% on your flight

$497

per person

Jan 17 - Jan 23

found 1 day ago

Roundtrip flight included

Boston (BOS) to Miami (MIA)

A full-service spa, an outdoor pool, and a restaurant are all featured at this aparthotel. Families will appreciate the playground and onsite laundry facilities. Enjoy the gym and unwind at the bar/lounge and poolside bar.

Avi Lux Stay

East Fort Lauderdale

$771

per person

Dec 7 - Dec 12

found 1 day ago

Roundtrip flight included

Boston (BOS) to Miami (MIA)

8 hot tubs, an outdoor pool, and a gym are all featured at this smoke-free aparthotel. WiFi in public areas is free. Valet parking, a 24-hour business center, and luggage storage are also offered.

The Retreat Collection at 1 Hotel & Homes South Beach

South Beach

$6,113

per person

Dec 7 - Dec 11

found 1 day ago

Roundtrip non-stop flight included

Boston (BOS) 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.

Broadway Suites Downtown by RocketStay

Coral Way

$689

per person

Jan 10 - Jan 17

found 1 day ago

Roundtrip flight included

New York (LGA) to Miami (MIA)

This apartment features a terrace, laundry facilities, and free self parking. Business travelers can take advantage of the express check-in. A garden and express check-out are also provided.

The Club - Pool - Gym - Parking - Heart of Brickell

Brickell

Save 100% on your flight

$1,571

per person

Dec 31 - Jan 6

found 1 day ago

Roundtrip flight included

Newark Liberty Intl. Airport (EWR) to Miami (MIA)

This apartment's 2 outdoor pools and 24-hour gym are among the featured amenities. Free self parking and luggage storage are also offered on site.

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

$304 nightly

$342 total

Nov 1 - Nov 2

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

$178 nightly

$200 total

Oct 26 - Oct 27

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

$149 nightly

$168 total

Oct 26 - Oct 27

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

$164 nightly

$180 total

Oct 27 - Oct 28

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 Islamorada FL

Free Cancellation

Reserve now, pay when you stay

$236 nightly

$266 total

Nov 19 - Nov 20

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

103800 Overseas Hwy Key Largo FL

Free Cancellation

Reserve now, pay when you stay

$259 nightly

$286 total

Oct 26 - Oct 27

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.

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 $497. 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.