Title: Windley Key Vacation Rentals from $299: Search Short-Term Rentals | 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)[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)[Windley Key Vacation Packages](https://expedia.com/Windley-Key.d553248635976197663.Destination-Travel-Guides)

![Windley Key Fossil Reef Geological State Park](https://images.trvl-media.com/place/6282211/331e71ab-ee65-4e64-bb08-32876871cf53.jpg?impolicy=fcrop&w=1200&h=500&q=medium)

![](https://images.trvl-media.com/place/6282211/331e71ab-ee65-4e64-bb08-32876871cf53.jpg?impolicy=fcrop&w=1200&h=500&q=medium)

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## Check prices for these dates

In two weeks

[Feb 27 - Mar 1](https://www.expedia.com/Hotel-Search?regionId=553248635976197663&startDate=2026-02-27&endDate=2026-03-01&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

In two months

[Apr 10 - Apr 12](https://www.expedia.com/Hotel-Search?regionId=553248635976197663&startDate=2026-04-10&endDate=2026-04-12&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

In three months

[May 8 - May 10](https://www.expedia.com/Hotel-Search?regionId=553248635976197663&startDate=2026-05-08&endDate=2026-05-10&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

In four months

[Jun 5 - Jun 7](https://www.expedia.com/Hotel-Search?regionId=553248635976197663&startDate=2026-06-05&endDate=2026-06-07&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

## Our top choices for Windley Key vacation rentals

![25-inch flat-screen TV with digital channels, TV](https://images.trvl-media.com/lodging/92000000/91750000/91743100/91743042/12c235b3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Premium bedding, individually decorated, free WiFi, bed sheets](https://images.trvl-media.com/lodging/92000000/91750000/91743100/91743042/b0169681.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![25-inch flat-screen TV with digital channels, TV](https://images.trvl-media.com/lodging/92000000/91750000/91743100/91743042/92a650b5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Terrace/patio](https://images.trvl-media.com/lodging/92000000/91750000/91743100/91743042/17a61bb5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Treasure Harbor

[](https://www.expedia.com/Islamorada-Hotels-Treasure-Harbor.h91743042.Hotel-Information)

Islamorada

9.0/10

Wonderful

(129 reviews)

"Very peaceful and comfortable stay! Dallas and Hannah were amazing hosts! Thank you so much !"

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Nick

$294 nightly

$331 total

Feb 22 - Feb 23

Total with taxes and fees

[](https://www.expedia.com/Islamorada-Hotels-Treasure-Harbor.h91743042.Hotel-Information)

![Private beach, sun loungers](https://images.trvl-media.com/lodging/79000000/78330000/78323400/78323367/6213e965.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Superior Cabin | Terrace/patio](https://images.trvl-media.com/lodging/79000000/78330000/78323400/78323367/84e1eccf.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Dock](https://images.trvl-media.com/lodging/79000000/78330000/78323400/78323367/235ba8b6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Superior Cabin | Private kitchen | Coffee/tea maker](https://images.trvl-media.com/lodging/79000000/78330000/78323400/78323367/4fafaddd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Kings Kamp

[](https://www.expedia.com/Key-Largo-Hotels-Kings-Kamp.h78323367.Hotel-Information)

Key Largo

8.6/10

Excellent

(28 reviews)

"Clean room, Beautiful view of the sea from the room window."

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Serhiy

$266 nightly

$299 total

Feb 17 - Feb 18

Total with taxes and fees

[](https://www.expedia.com/Key-Largo-Hotels-Kings-Kamp.h78323367.Hotel-Information)

![On the beach, sun loungers, beach umbrellas, beach towels](https://images.trvl-media.com/lodging/55000000/54780000/54774300/54774228/dd7d4fab.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Premium bedding, pillowtop beds, in-room safe, individually decorated](https://images.trvl-media.com/lodging/55000000/54780000/54774300/54774228/a064415d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Balcony view](https://images.trvl-media.com/lodging/55000000/54780000/54774300/54774228/95dbc957.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV, Netflix, Hulu, streaming services](https://images.trvl-media.com/lodging/55000000/54780000/54774300/54774228/fcc01350.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### The Islands of Islamorada

[](https://www.expedia.com/Islamorada-Hotels-The-Islands-Of-Islamorada.h54774228.Hotel-Information)

Matecumbe

9.8/10

Exceptional

(70 reviews)

"Amazing stay, can’t wait to stay there again!"

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Anonymous traveler

$948 nightly

$1,067 total

Feb 26 - Feb 27

Total with taxes and fees

[](https://www.expedia.com/Islamorada-Hotels-The-Islands-Of-Islamorada.h54774228.Hotel-Information)

![Exterior](https://images.trvl-media.com/lodging/12000000/11950000/11945900/11945889/19240ce2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/12000000/11950000/11945900/11945889/98989626.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Economy Room | 1 bedroom, free WiFi](https://images.trvl-media.com/lodging/12000000/11950000/11945900/11945889/f0ed1fc9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Standard Room, 1 Bedroom, Kitchen, Pool View | Living area | TV](https://images.trvl-media.com/lodging/12000000/11950000/11945900/11945889/3602f78f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Breezy Palms Resort

[](https://www.expedia.com/Islamorada-Hotels-Breezy-Palms-Resort.h11945889.Hotel-Information)

Matecumbe

8.8/10

Excellent

(618 reviews)

"Friendly staff, beautiful peaceful beach, great room with a big comfy bed and all that you might need. "

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Alexander

$280 nightly

$315 total

Mar 4 - Mar 5

Total with taxes and fees

[](https://www.expedia.com/Islamorada-Hotels-Breezy-Palms-Resort.h11945889.Hotel-Information)

![Exterior](https://images.trvl-media.com/lodging/109000000/108750000/108743400/108743380/dd2c750f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![1 bedroom, premium bedding, individually furnished, blackout drapes](https://images.trvl-media.com/lodging/109000000/108750000/108743400/108743380/dc4f4949.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![55-inch Smart TV with digital channels, books](https://images.trvl-media.com/lodging/109000000/108750000/108743400/108743380/96d842c8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![In-room dining](https://images.trvl-media.com/lodging/109000000/108750000/108743400/108743380/c244835e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Premium Floating Bungalow by Stay Ombi

[](https://www.expedia.com/Key-Largo-Hotels-Premium-Floating-Bungalow-By-Stay-Ombi.h108743380.Hotel-Information)

Key Largo

10/10

Exceptional

(1 review)

$828 nightly

$932 total

Feb 18 - Feb 19

Total with taxes and fees

[](https://www.expedia.com/Key-Largo-Hotels-Premium-Floating-Bungalow-By-Stay-Ombi.h108743380.Hotel-Information)

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.

[View all properties](https://expedia.com/Hotel-Search?startDate=2026-02-28&endDate=2026-03-01&regionId=553248635976197663&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&openPlayBack=true)

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## 

The Annual Vacation Sale

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## Find vacation rentals that suit your style

Aparthotels

[](https://www.expedia.com/Hotel-Search?destination=Windley+Key%2C+Florida%2C+United+States+of+America&regionId=553248635976197663&latLong=24.954588%2C-80.592445&adults=2&startDate=2026-05-15&d1=2026-05-15&endDate=2026-05-18&d2=2026-05-18&lodging=APART_HOTEL)

Apartments

[](https://www.expedia.com/Hotel-Search?destination=Windley+Key%2C+Florida%2C+United+States+of+America&regionId=553248635976197663&latLong=24.954588%2C-80.592445&adults=2&startDate=2026-05-15&d1=2026-05-15&endDate=2026-05-18&d2=2026-05-18&lodging=APARTMENT)

Private vacation homes

[](https://www.expedia.com/Hotel-Search?destination=Windley+Key%2C+Florida%2C+United+States+of+America&regionId=553248635976197663&latLong=24.954588%2C-80.592445&adults=2&startDate=2026-05-15&d1=2026-05-15&endDate=2026-05-18&d2=2026-05-18&lodging=VACATION_HOME)

Condos

[](https://www.expedia.com/Hotel-Search?destination=Windley+Key%2C+Florida%2C+United+States+of+America&regionId=553248635976197663&latLong=24.954588%2C-80.592445&adults=2&startDate=2026-05-15&d1=2026-05-15&endDate=2026-05-18&d2=2026-05-18&lodging=CONDO)

Cottages

[](https://www.expedia.com/Hotel-Search?destination=Windley+Key%2C+Florida%2C+United+States+of+America&regionId=553248635976197663&latLong=24.954588%2C-80.592445&adults=2&startDate=2026-05-15&d1=2026-05-15&endDate=2026-05-18&d2=2026-05-18&lodging=COTTAGE)

Villas

[](https://www.expedia.com/Hotel-Search?destination=Windley+Key%2C+Florida%2C+United+States+of+America&regionId=553248635976197663&latLong=24.954588%2C-80.592445&adults=2&startDate=2026-05-15&d1=2026-05-15&endDate=2026-05-18&d2=2026-05-18&lodging=VILLA)

Houseboats

[](https://www.expedia.com/Hotel-Search?destination=Windley+Key%2C+Florida%2C+United+States+of+America&regionId=553248635976197663&latLong=24.954588%2C-80.592445&adults=2&startDate=2026-05-15&d1=2026-05-15&endDate=2026-05-18&d2=2026-05-18&lodging=HOUSE_BOAT)

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## Top Windley Key Hotel Reviews

![Lime Tree Bay Resort](https://images.trvl-media.com/lodging/1000000/890000/882300/882254/6f2246e8_y.jpg)

### Lime Tree Bay Resort

10/10 Excellent

"Very nice resort...great view...employees always seemed friendly. We have already said "we will return"."

[](https://expedia.com/Long-Key-Hotels-Lime-Tree-Bay-Resort.h882254.Hotel-Information)

![Coconut Cove Resort and Marina](https://images.trvl-media.com/lodging/5000000/4190000/4182600/4182524/667446d9_y.jpg)

### Coconut Cove Resort and Marina

10/10 Excellent

"Friendly and very helpful staff"

[](https://expedia.com/Islamorada-Hotels-Coconut-Cove-Resort-And-Marina.h4182524.Hotel-Information)

![Chesapeake Beach Resort](https://images.trvl-media.com/lodging/1000000/10000/4200/4170/689f4306_y.jpg)

### Chesapeake Beach Resort

10/10 Excellent

"Just perfect "

[](https://expedia.com/Islamorada-Hotels-Chesapeake-Beach-Resort.h4170.Hotel-Information)

![Reefhouse Resort & Marina](https://images.trvl-media.com/lodging/1000000/10000/3500/3427/af093823_y.jpg)

### Reefhouse Resort & Marina

10/10 Excellent

"Beautiful resort, friendly staff "

[](https://expedia.com/Key-Largo-Hotels-Reefhouse-Resort-Marina.h3427.Hotel-Information)

![Marina Del Mar Resort and Marina](https://images.trvl-media.com/lodging/1000000/10000/5200/5114/d42f8885_y.jpg)

### Marina Del Mar Resort and Marina

10/10 Excellent

"Staff was wonderful and ver accommodating! Room was very clean and the grounds are beautiful. Breakfast by pool is wonderful! "

[](https://expedia.com/Key-Largo-Hotels-Marina-Del-Mar-Resort-And-Marina.h5114.Hotel-Information)

![Amara Cay Resort](https://images.trvl-media.com/lodging/1000000/70000/62000/61976/84b50729_y.jpg)

### Amara Cay Resort

10/10 Excellent

"Great staff, good view from room and breakfast was superb. Thanks."

[](https://expedia.com/Islamorada-Hotels-Amara-Cay-Resort.h61976.Hotel-Information)

![Bayside Inn Key Largo](https://images.trvl-media.com/lodging/1000000/30000/22700/22657/419b7787_y.jpg)

### Bayside Inn Key Largo

10/10 Excellent

"The room was nice and the amenities fabulous. The sunset was awesome too "

[](https://expedia.com/Key-Largo-Hotels-Bayside-Inn-Key-Largo.h22657.Hotel-Information)

![The Pelican Key Largo Cottages](https://images.trvl-media.com/lodging/7000000/6840000/6839400/6839376/f35b06df_y.jpg)

### The Pelican Key Largo Cottages

10/10 Excellent

"Everyone was great and everything was neat and clean."

[](https://expedia.com/Key-Largo-Hotels-The-Pelican-Key-Largo-Cottages.h6839376.Hotel-Information)

![Creekside Inn](https://images.trvl-media.com/lodging/2000000/1580000/1576800/1576773/5e43c05b_y.jpg)

### Creekside Inn

10/10 Excellent

"Clean and comfortable room. Beautiful view of creek."

[](https://expedia.com/Tavernier-Hotels-Creekside-Inn-Islamorada.h1576773.Hotel-Information)

## Find out more about Windley Key

**Everything you need to know about Windley Key vacation rentals**

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Windley Key vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. The list goes on, and on …and on.

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Windley Key vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

**Windley Key vacation rentals: An excellent choice for every season**

Whenever you want to travel, a warm welcome awaits you in Windley Key. If you’re looking for a little peace, consider booking during the quieter low season months. For more hustle and bustle, you may prefer to visit Windley Key in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $299 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

**How to find incredible deals on Windley Key rentals**

At Expedia, we put the best Windley Key vacation rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia.

To find some top Windley Key rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Windley Key vacation.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Windley Key. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.

## Explore a world of travel with Expedia

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- All accommodation types in Windley Key

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- [Vacation Homes in Windley Key ](https://expedia.com/Windley-Key-Private-Vacation-Homes.d553248635976197663-aaPrivateVacationHomes.Travel-Guide-Accommodation)
- [Condo Rentals in Windley Key ](https://expedia.com/Windley-Key-Condos.d553248635976197663-aaCondos.Travel-Guide-Accommodation)
- [Apartments in Windley Key ](https://expedia.com/Windley-Key-Apartments.d553248635976197663-aaApartments.Travel-Guide-Accommodation)
- [Villas in Windley Key ](https://expedia.com/Windley-Key-Villas.d553248635976197663-aaVillas.Travel-Guide-Accommodation)
- [Cottages in Windley Key ](https://expedia.com/Windley-Key-Cottages.d553248635976197663-aaCottages.Travel-Guide-Accommodation)
- [Houseboats in Windley Key ](https://expedia.com/Windley-Key-Houseboats.d553248635976197663-aaHouseboats.Travel-Guide-Accommodation)
- [Aparthotels in Windley Key ](https://expedia.com/Windley-Key-Apart-Hotels.d553248635976197663-aaApartHotels.Travel-Guide-Accommodation)
- [RV Parks in Windley Key ](https://expedia.com/Windley-Key-RV-Parks.d553248635976197663-aaRVParks.Travel-Guide-Accommodation)
- [Resorts in Windley Key ](https://expedia.com/Windley-Key-Resorts.d553248635976197663-aaResorts.Travel-Guide-Accommodation)
- [Motels in Windley Key ](https://expedia.com/Windley-Key-Motels.d553248635976197663-aaMotels.Travel-Guide-Accommodation)
- [Guest Houses in Windley Key ](https://expedia.com/Windley-Key-Guest-Houses.d553248635976197663-aaGuestHouses.Travel-Guide-Accommodation)
- [Cabin Rentals in Windley Key ](https://expedia.com/Windley-Key-Cabins.d553248635976197663-aaCabins.Travel-Guide-Accommodation)
- [Lodges in Windley Key ](https://expedia.com/Windley-Key-Lodges.d553248635976197663-aaLodges.Travel-Guide-Accommodation)
- [Condo Resorts in Windley Key ](https://expedia.com/Windley-Key-Condominium-Resort.d553248635976197663-aaCondominiumResort.Travel-Guide-Accommodation)

### Expedia's Latest Trends

Hotels

- [Hotel Rooms in Lower Matecumbe Key](https://expedia.com/Lower-Matecumbe-Key-Hotels.d553248635975749077.Travel-Guide-Hotels)
- [Lido Key Oceanfront Hotels](https://expedia.com/Lido-Key-Hotels-Oceanfront-Hotels.0-0-d6138897-tOceanfrontHotels.Travel-Guide-Filter-Hotels)
- [Hurricane Monument hotels](https://expedia.com/Hurricane-Monument-Hotels.0-l6063543-0.Travel-Guide-Filter-Hotels)
- [Amelia Island Beach Hotels](https://expedia.com/Amelia-Island-Hotels-Beach-Hotel.0-0-d10814-tBeachHotel.Travel-Guide-Filter-Hotels)
- [Hotel Rooms in South Tampa](https://expedia.com/South-Tampa-Hotels.d6321582.Travel-Guide-Hotels)
- [Anne's Beach hotels](https://expedia.com/Annes-Beach-Hotels.0-l6282204-0.Travel-Guide-Filter-Hotels)
- [Hotel Rooms in Honeymoon Island State Park](https://expedia.com/Honeymoon-Island-State-Park-Hotels.d6160046.Travel-Guide-Hotels)
- [Lido Key Beach Hotels](https://expedia.com/Lido-Key-Hotels-Beach-Hotel.0-0-d6138897-tBeachHotel.Travel-Guide-Filter-Hotels)
- [Hotel Rooms in Bahia Honda Key](https://expedia.com/Bahia-Honda-Key-Hotels.d553248635083902001.Travel-Guide-Hotels)
- [Amelia Island Oceanfront Hotels](https://expedia.com/Amelia-Island-Hotels-Oceanfront-Hotels.0-0-d10814-tOceanfrontHotels.Travel-Guide-Filter-Hotels)
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- [Hotel Rooms in Amelia Island](https://expedia.com/Amelia-Island-Hotels.d10814.Travel-Guide-Hotels)
- [Hotel Rooms in Stock Island](https://expedia.com/Stock-Island-Hotels.d180166.Travel-Guide-Hotels)
- [Hotel Rooms in Manasota Key](https://expedia.com/Manasota-Key-Hotels.d3000431268.Travel-Guide-Hotels)
- [Hotel Rooms in Sugarloaf Key](https://expedia.com/Sugarloaf-Key-Hotels.d183126.Travel-Guide-Hotels)
- [Florida Keys Brewing Co. hotels](https://expedia.com/Florida-Keys-Brewing-Co-Hotels.0-l553248635997958830-0.Travel-Guide-Filter-Hotels)

Flights

- [Flights to JAX](https://expedia.com/Cheap-Flights-To-Amelia-Island.d10814.Travel-Guide-Flights)

Cars

- [Car rentals in Amelia Island](https://expedia.com/Car-Rentals-In-Amelia-Island.d10814.Car-Rental-Guide)

Activities

- [Things to do in South Tampa](https://expedia.com/Things-To-Do-In-South-Tampa.d6321582.Travel-Guide-Activities)
- [Things to do in Cudjoe Key](https://expedia.com/Things-To-Do-In-Cudjoe-Key.d3000430966.Travel-Guide-Activities)
- [Things to do in Boca Chica Key](https://expedia.com/Things-To-Do-In-Boca-Chica-Key.d553248635083916609.Travel-Guide-Activities)

Packages

- [Holiday in Amelia Island](https://expedia.com/Amelia-Island.d10814.Destination-Travel-Guides)
- [Sunset Drive Beach](https://expedia.com/Sunset-Drive-Beach-Matecumbe.d672757825479704576.Vacation-Attraction)
- [Anne's Beach](https://expedia.com/Annes-Beach-Matecumbe.d6282204.Vacation-Attraction)

Vacation Rentals

- [Amelia Island Vacation Rental](https://expedia.com/Amelia-Island-Vacation-Rentals.d10814.Travel-Guide-VacationRentals)

General

- [Visit Honeymoon Island State Park](https://expedia.com/Honeymoon-Island-State-Park.dx6160046)
- [Visit Shell Island](https://expedia.com/Shell-Island.dx6312110)
- [Visit Sugarloaf Key](https://expedia.com/Sugarloaf-Key.dx183126)
- [Visit Amelia Island](https://expedia.com/Amelia-Island.dx10814)
- [Visit Upper Matecumbe Key](https://expedia.com/Upper-Matecumbe-Key.dx553248635975749648)

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