Title: Windley Key Vacation Packages 2026 from $426 | 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 $426

## 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.

![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

Save 100% on your flight

$426

per person

Apr 25 - Apr 30

found 1 day 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

![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

$430

per person

May 3 - May 6

found 1 day ago

Roundtrip flight included

Boston (BOS) to Miami (MIA)

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

The lodge was cute and great location. We stayed one night and enjoyed the visit. We had a walkout patio to the boat dock and my boyfriend saw 2 manatee’s in the swimming by before we left in the morning ☺️

Reviewed on Feb 22, 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

$959

per person

May 1 - May 8

found 1 day ago

Roundtrip flight included

Boston (BOS) to Miami (MIA)

9.2/10 Wonderful! (394 reviews)

Staff was top notch!! They were helpful and kind and always happy to interact with us.

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

$486

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)

nice location, good room. nice breakfast and evening reception

Reviewed on Feb 22, 2026

![Bay Breeze Premium Apartments By Eskape Collection](https://images.trvl-media.com/lodging/28000000/27610000/27603500/27603405/c37fc122_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### Bay Breeze Premium Apartments By Eskape Collection

$585

per person

Apr 25 - May 1

found 1 day ago

Roundtrip flight included

Boston (BOS) to Miami (MIA)

8.6/10 Excellent! (189 reviews)

The staff was courteous and helpful. The apartment was equipped with basic essentials. The area was quiet. I would suggest adding oven mittens in the kitchen as there was nothing to use to take the pan out of the oven with.

Reviewed on Jan 21, 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/2026-03-23/2026-03-30/?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

$390 nightly

$438 total

Mar 5 - Mar 6

Total with taxes and fees

9/10 Wonderful! (156 reviews)

Everything was amazing!

Reviewed on Feb 23, 2026

[](https://expedia.com/Hotel-Search?startDate=3%2F5%2F2026&endDate=3%2F6%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! (1,004 reviews)

The room was clean but tired. The location is good but highway noise. The staff were OK. The food truck was very good.

Reviewed on Feb 22, 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

$358 nightly

$403 total

Mar 2 - Mar 3

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%2F2%2F2026&endDate=3%2F3%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%2F24%2F2026&endDate=2%2F25%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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