Title: Windley Key Vacation Packages 2026 from $441 | Expedia.com

[Windley Key Travel Guide](https://expedia.com/Windley-Key.dx553248635976197663)[Hotels in Windley Key](https://expedia.com/Windley-Key-Hotels.d553248635976197663.Travel-Guide-Hotels)[Vacation Rentals in Windley Key](https://expedia.com/Windley-Key-Vacation-Rentals.d553248635976197663.Travel-Guide-VacationRentals)[Flights to Windley Key](https://expedia.com/Cheap-Flights-To-Windley-Key.d553248635976197663.Travel-Guide-Flights)[Things to do in Windley Key](https://expedia.com/Things-To-Do-In-Windley-Key.d553248635976197663.Travel-Guide-Activities)[Car Rentals in Windley Key](https://expedia.com/Car-Rentals-In-Windley-Key.d553248635976197663.Car-Rental-Guide)

![](https://images.trvl-media.com/place/553248635997958830/30b22f53-286f-436b-ae7a-d035c9062e6c.jpg?impolicy=fcrop&w=1200&h=300&q=medium)

# Windley Key Vacations from $441

## Book a Hotel + Flight or Car together to unlock savings

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## The Latest Windley Key vacation packages

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

![President Hotel Villa](https://images.trvl-media.com/lodging/11000000/10620000/10612900/10612810/06988314_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### President Hotel Villa

South Beach

Save 100% on your flight

$441

per person

May 15 - May 20

found 1 day ago

Roundtrip flight included

Boston (BOS) to Miami (MIA)

8.2/10 Very Good! (997 reviews)

nice location, good room. nice breakfast and evening reception

Reviewed on Feb 22, 2026

![Casablanca Miami Beach](https://images.trvl-media.com/lodging/32000000/31660000/31652200/31652150/628e521a_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### Casablanca Miami Beach

North Beach

$2,008

per person

May 18 - May 22

found 22 hours ago

Roundtrip flight included

Boston (BOS) to Miami (MIA)

5.8/10 (311 reviews)

Room was clean and great location beside the beach. Room had kitchette and big fridge, microwave etc. so was great. It was dated and internet didn't work in our room but worked well in the lobby. Great value for money :) happy with it.

Reviewed on Feb 22, 2026

![W South Beach](https://images.trvl-media.com/lodging/1000000/20000/11900/11881/f8e7300f_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### W South Beach

South Beach

$2,916

per person

Apr 30 - May 3

found 1 day ago

Roundtrip flight included

Boston (BOS) to Miami (MIA)

9.2/10 Wonderful! (1,002 reviews)

Room was Amazing very clean! Staff everywhere was welcoming and friendly

Reviewed on Feb 8, 2026

![Creekside Inn](https://images.trvl-media.com/lodging/2000000/1580000/1576800/1576773/5e43c05b_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### Creekside Inn

$810

per person

Apr 7 - Apr 13

found 1 day ago

Roundtrip flight included

Boston (BOS) to Miami (MIA)

8/10 Very Good! (1,004 reviews)

118, the room was clean and the customer service was good.

Reviewed on Feb 24, 2026

![Pelican Hotel](https://images.trvl-media.com/lodging/1000000/60000/55100/55046/22b81b04_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### Pelican Hotel

South Beach

$476

per person

May 15 - May 20

found 1 day ago

Roundtrip flight included

Boston (BOS) to Miami (MIA)

9.2/10 Wonderful! (394 reviews)

Great cozy old hotel, location is very good, the restaurant and foods awesome, they made a mix up in our first included breakfast and took me a long time of argument with the hotel manager to convince him for their lack of information and to get my money back, that and 40 minutes waiting to get my car back from valet are the only reason to give them 4 stars otherwise the stay was pleasant

Reviewed on Feb 24, 2026

Don't see what you're looking for?

See all available trips from Columbus to Windley Key

[View all trips](https://expedia.com/go/package/search/FlightHotel/2026-03-25/2026-04-01/?FromAirport=Columbus,%20Ohio,%20United%20States%20of%20America&Destination=MIA&NumRoom=1&NumAdult=2&NumChild=0&paandie=true)

![](https://forever.travel-assets.com/flex/flexmanager/images/2026/02/06/expedia-sale-2026-desktop-us-ca.jpg?impolicy=fcrop&w=1400&h=600&q=mediumHigh)

## 

The Annual Vacation Sale

Members save up to 40% on hotels and homes. Plan this year’s big trip and save.

[Book now](https://expedia.com/deals?rfrr=PKG_SPRING_PROMO_553248635976197663)

### Discover the most popular places to visit in Windley Key

![Windley Key Fossil Reef Geological State Park](https://images.trvl-media.com/place/6282211/9f8e583b-bc9a-4a16-b731-daa0b5c7f87b.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

#### Windley Key Fossil Reef Geological State Park

Explore the fossilized reef of a former quarry in this island park, as you learn about the history and ecology from the interpretive trails.

[](https://expedia.com/Windley-Key-Fossil-Reef-Geological-State-Park-Islamorada.d6282211.Vacation-Attraction)

## Windley Key Hotel Deals

![Three Waters Resort and Marina, Islamorada, a Tribute Portfolio Resort](https://images.trvl-media.com/lodging/1000000/20000/11900/11864/d10a018b_y.jpg?impolicy=resizecrop&rw=340&ch=150)

### 

Three Waters Resort and Marina, Islamorada, a Tribute Portfolio Resort

84001 Overseas Hwy Islamorada FL

Fully refundableReserve now, pay when you stay

$483 nightly

$544 total

Mar 4 - Mar 5

Total with taxes and fees

9/10 Wonderful! (157 reviews)

All was fantastic. Very nice staff. Clean room. Highly recommended

Reviewed on Feb 23, 2026

[](https://expedia.com/Hotel-Search?startDate=3%2F4%2F2026&endDate=3%2F5%2F2026&selected=11864&PinnedHotelID=11864&HadPinnedHotel=true&regionId=553248635976197663)

![Fisher Inn Resort & Marina](https://images.trvl-media.com/lodging/4000000/3280000/3274400/3274374/9ae0ece9_y.jpg?impolicy=resizecrop&rw=340&ch=150)

### 

Fisher Inn Resort & Marina

84951 Overseas Hwy Islamorada FL

Fully refundableReserve now, pay when you stay

$299 nightly

$336 total

Mar 1 - Mar 2

Total with taxes and fees

8.4/10 Very Good! (1,000 reviews)

Beautiful property! Very clean, view was amazing!

Reviewed on Feb 24, 2026

[](https://expedia.com/Hotel-Search?startDate=3%2F1%2F2026&endDate=3%2F2%2F2026&selected=3274374&PinnedHotelID=3274374&HadPinnedHotel=true&regionId=553248635976197663)

![Coconut Cove Resort and Marina](https://images.trvl-media.com/lodging/5000000/4190000/4182600/4182524/667446d9_y.jpg?impolicy=resizecrop&rw=340&ch=150)

### 

Coconut Cove Resort and Marina

84801 Overseas Highway Islamorada FL

$362 nightly

$408 total

Mar 9 - Mar 10

Total with taxes and fees

9.2/10 Wonderful! (199 reviews)

Cool place, definitely not a first class experience, but we loved it. Room clean, grounds nice, the animals running around were great. Best part was staff.the Lady at the desk was fantastic, and everyone we came across were very polite and friendly. I would 100% return.

Reviewed on Feb 23, 2026

[](https://expedia.com/Hotel-Search?startDate=3%2F9%2F2026&endDate=3%2F10%2F2026&selected=4182524&PinnedHotelID=4182524&HadPinnedHotel=true&regionId=553248635976197663)

[See all 2,741 properties in Windley Key](https://expedia.com/Hotel-Search?rfrrid=TG.LP.Hotels.Package&startDate=2%2F26%2F2026&endDate=2%2F27%2F2026&regionId=553248635976197663)

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.

## Find the Best Windley Key Vacation Packages

## Windley Key Essential Information

| Language        | English                      |
| --------------- | ---------------------------- |
| Currency        | U.S dollars                  |
| Closest Airport | Key West Intl. Airport (EYW) |

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- [Aparthotels in Islamorada ](https://www.expedia.com/Islamorada-Apart-Hotels.d10768-aaApartHotels.Travel-Guide-Accommodation)

- [Flights from Plantation Key ](https://www.expedia.com/lp/flights/553248635083898347/flights-from-plantation-key)
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- [Windley Key Fossil Reef Geological State Park ](https://www.expedia.com/Windley-Key-Fossil-Reef-Geological-State-Park-Islamorada.d6282211.Vacation-Attraction)
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- [Islamorada County Park ](https://www.expedia.com/Islamorada-County-Park-Islamorada.d553248621532652353.Vacation-Attraction)
- [Islamorada Vacations ](https://www.expedia.com/Islamorada.d10768.Destination-Travel-Guides)
- [Visit Islamorada ](https://www.expedia.com/Islamorada.dx10768)

- [Car rentals near Islamorada ](https://www.expedia.com/Car-Rentals-In-Islamorada.d10768.Car-Rental-Guide)
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- [Convertible Car Rentals in Islamorada ](https://www.expedia.com/Convertible-Car-Rentals-In-Islamorada.d10768-tConvertible.Car-Rental-Guide-Class)

- [Islamorada Vacation Rentals ](https://www.expedia.com/Islamorada-Vacation-Rentals.d10768.Travel-Guide-VacationRentals)

- [Things to do in Islamorada ](https://www.expedia.com/Things-To-Do-In-Islamorada.d10768.Travel-Guide-Activities)

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