Windley Key Vacation Packages 2026 from $580

Windley Key flight + hotel vacation packages

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

Family Pool Home by Hollywood Beach

Hollywood Hills

$580

per person

Jul 16 - Jul 19

found 1 day ago

Roundtrip flight included

Dallas (DFW) 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.

3BR Pool House Sleeps 8

Driftwood

$627

per person

Jul 16 - Jul 19

found 1 day ago

Roundtrip flight included

Dallas (DFW) to Miami (MIA)

An outdoor pool, free self parking, and barbecue grills are featured at this vacation home. WiFi in public areas is free. A garden is also provided.

Brickell Bay 3304

Brickell

$593

per person

Jul 15 - Jul 18

found 14 hours ago

Roundtrip flight included

Boston (BOS) 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.

Casablanca Miami Beach

North Beach

$3,981

per person

Jul 12 - Jul 19

found 1 day ago

Roundtrip flight included

Boston (BOS) 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.

Brickell Bay 3318

Brickell

$593

per person

Jul 15 - Jul 18

found 16 hours ago

Roundtrip flight included

Boston (BOS) 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.

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

$322 nightly

$362 total

May 25 - May 26

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

$198 nightly

$223 total

Apr 30 - May 1

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

$179 nightly

$201 total

Apr 29 - Apr 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

$210 nightly

$232 total

Apr 30 - May 1

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

Chesapeake Beach Resort

83409 Overseas Hwy Islamorada FL

Free Cancellation

Reserve now, pay when you stay

$232 nightly

$261 total

May 10 - May 11

Total with taxes and fees

A private beach, a marina, and 2 outdoor pools are all featured at this smoke-free hotel. Enjoy a day at the beach kayaking, or relax with sun loungers. Unwind with a drink at the bar/lounge and enjoy perks like free continental breakfast and free WiFi.

On private beach

Pool

Cheeca Lodge & Spa

81801 Overseas Highway, Mile Marker 82 Islamorada FL

Free Cancellation

Reserve now, pay when you stay

$337 nightly

$379 total

Apr 29 - Apr 30

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

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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 $580. 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.