Windley Key Vacation Packages 2026 from $443

Windley Key flight + hotel vacation packages

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

Brickell Bay 3505

Brickell

$443

per person

Jul 16 - Jul 19

found 1 day ago

Roundtrip flight included

Atlanta (ATL) to Miami (MIA)

This apartment features dry cleaning, laundry facilities, and free self parking. Staff at the 24-hour front desk can provide around-the-clock assistance.

The W - Bayshore Unit 1003

East Fort Lauderdale

$460

per person

Jul 16 - Jul 19

found 1 day ago

Roundtrip flight included

Atlanta (ATL) to Miami (MIA)

This apartment features dry cleaning, laundry facilities, and valet parking. Staff at the 24-hour front desk can provide around-the-clock assistance.

Brickell Bay 3318

Brickell

$526

per person

Jul 10 - Jul 13

found 1 day ago

Roundtrip flight included

New York (NYC) to Miami (MIA)

This apartment features dry cleaning, laundry facilities, and free self parking. Staff at the 24-hour front desk can provide around-the-clock assistance.

Brickell Bay 3304

Brickell

$526

per person

Jul 10 - Jul 13

found 1 day ago

Roundtrip flight included

New York (NYC) to Miami (MIA)

This apartment features dry cleaning, laundry facilities, and free self parking. Staff at the 24-hour front desk can provide around-the-clock assistance.

Family Pool Home by Hollywood Beach

Hollywood Hills

$1,110

per person

Jun 26 - Jul 2

found 1 day ago

Roundtrip flight included

New York (JFK) to Miami (MIA)

An outdoor pool, free self parking, and laundry facilities are featured at this vacation home. WiFi in public areas is free. Barbecue grills and a virtual front desk are also provided.

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

$285 nightly

$321 total

Jun 8 - Jun 9

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

$164 nightly

$185 total

Jun 3 - Jun 4

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

$199 nightly

$224 total

May 12 - May 13

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

$245 nightly

$271 total

May 10 - May 11

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

Reefhouse Resort & Marina

103800 Overseas Hwy Key Largo FL

Free Cancellation

Reserve now, pay when you stay

$319 nightly

$354 total

May 10 - May 11

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.

On private beach

Pool

Waterside Suites & Marina

201 Ocean Drive Key Largo FL

Free Cancellation

Reserve now, pay when you stay

$143 nightly

$161 total

May 27 - May 28

Total with taxes and fees

A marina and an outdoor pool are featured at this smoke-free hotel. WiFi in public areas is free. A terrace, a picnic area, and luggage storage are also on offer.

Pool

Pet friendly

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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

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

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 $443. 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.