Title: Windley Key Vacation Packages 2026 from $422 | 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 $422

## 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.

![Solé Miami, A Noble House Resort](https://images.trvl-media.com/lodging/3000000/2810000/2803900/2803820/387d2cd6_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### Solé Miami, A Noble House Resort

Ocean Four

$422

per person

Apr 25 - Apr 30

found 1 day ago

Roundtrip flight included

Boston (BOS) to Miami (MIA)

8.4/10 Very Good! (1,935 reviews)

staff was awesome, room was great, elevators extremely slow

Reviewed on Feb 12, 2026

![Cavalier Hotel South Beach](https://images.trvl-media.com/lodging/1000000/20000/13600/13579/c0c3faa8_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### Cavalier Hotel South Beach

South Beach

$528

per person

Apr 25 - Apr 30

found 1 day ago

Roundtrip flight included

Boston (BOS) to Miami (MIA)

8.4/10 Very Good! (1,001 reviews)

The Cavalier Hotel has so much character. We loved the history and vintage feel. Can't wait to stay there again.

Reviewed on Feb 18, 2026

![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

$453

per person

Apr 25 - Apr 30

found 1 day ago

Roundtrip flight included

Boston (BOS) to Miami (MIA)

8.2/10 Very Good! (997 reviews)

Room was clean only had a problem with the toilet it took them awhile to come fix it the breakfast was good and staff definitely did everything they could to make our stay comfortable even until check out they held our bags for us because we had a later flight from our check out.

Reviewed on Feb 15, 2026

![President Hotel](https://images.trvl-media.com/lodging/1000000/580000/575900/575859/5a013cab_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### President Hotel

South Beach

$453

per person

Apr 25 - Apr 30

found 1 day ago

Roundtrip flight included

Boston (BOS) to Miami (MIA)

8.4/10 Very Good! (1,775 reviews)

Location was awesome but the room and bathroom was very very small for 2 queen beds. Room also smelled very musty. Sebastian at the bar was very kind and made us 2 great welcome drinks. Would not stay here again based on the size and musty smell.

Reviewed on Feb 18, 2026

![The Penguin Hotel](https://images.trvl-media.com/lodging/1000000/70000/62900/62824/d4ab7ebb_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### The Penguin Hotel

South Beach

$422

per person

Apr 25 - Apr 30

found 1 day ago

Roundtrip flight included

Boston (BOS) to Miami (MIA)

8.2/10 Very Good! (1,491 reviews)

The room was very clean and the staff was very friendly.

Reviewed on Feb 16, 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/2026-03-18/2026-03-25/?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

$449 nightly

$505 total

Mar 2 - Mar 3

Total with taxes and fees

9/10 Wonderful! (150 reviews)

The housekeeping services were not good. Staff was delightful at all locations; but housekeepers did not do a good job.

Reviewed on Feb 17, 2026

[](https://expedia.com/Hotel-Search?startDate=3%2F2%2F2026&endDate=3%2F3%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

$316 nightly

$356 total

Mar 1 - Mar 2

Total with taxes and fees

8.4/10 Very Good! (1,007 reviews)

Location

Reviewed on Feb 17, 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

$366 nightly

$412 total

Mar 1 - Mar 2

Total with taxes and fees

9.2/10 Wonderful! (193 reviews)

Exceptional staff. Very clean and well kept

Reviewed on Feb 17, 2026

[](https://expedia.com/Hotel-Search?startDate=3%2F1%2F2026&endDate=3%2F2%2F2026&selected=4182524&PinnedHotelID=4182524&HadPinnedHotel=true&regionId=553248635976197663)

[See all 2,758 properties in Windley Key](https://expedia.com/Hotel-Search?rfrrid=TG.LP.Hotels.Package&startDate=2%2F19%2F2026&endDate=2%2F20%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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- [Minneapolis - St. Paul to Islamorada ](https://www.expedia.com/lp/flights/178287/10768/minneapolis-st-paul-to-islamorada)

- [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)
- [Hertz Rental Cars in Islamorada ](https://www.expedia.com/Hertz-Car-Rentals-In-Islamorada.d10768-c40.Car-Rental-Guide-Suppliers)
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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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