Title: Florida Keys Adventure Vacations 2026 | Expedia.com

![](https://images.trvl-media.com/place/6246822/f00ad239-b8ad-4f0c-b162-acc6426db1e2.jpg?impolicy=fcrop&w=1200&h=300&q=medium)

# Florida Keys Adventure Vacations

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

- ##  
Plan, book, travel with confidence
- ###  
Better together  
Save up to $1,045 when you book a flight and hotel together\*
- ###  
Find the right fit  
With over 300,000 hotels worldwide, it's easy to create a perfect package
- ###  
Rest easy  
Plan, book, and manage your trip all in one place

## Top Adventure vacation packages in Florida Keys

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

![Hawks Cay Resort](https://images.trvl-media.com/lodging/1000000/10000/6100/6068/8671ba74_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### Hawks Cay Resort

$551

per person

May 2 - May 5

found 1 day ago

Roundtrip flight included

Philadelphia (PHL) to Miami (MIA)

8/10 Very Good! (1,015 reviews)

Staff were friendly and helpful. My family enjoyed the pools and Lagoon. We also enjoyed the marina and the restaurants on the resort.

Reviewed on Mar 30, 2026

![La Siesta Resort & Villas](https://images.trvl-media.com/lodging/3000000/2480000/2477600/2477508/18023e21_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### La Siesta Resort & Villas

Matecumbe

Save 100% on your flight

$653

per person

Jun 2 - Jun 5

found 11 hours ago

Roundtrip non-stop flight included

Kansas City (MCI) to Miami (MIA)

8.8/10 Excellent! (1,004 reviews)

Staff was nice. The rooms are old. Not that clean. They need a coat of new paint too. The bathroom was dirty. The shuttle took 30 min and he didn't show up.

Reviewed on Apr 1, 2026

![Tranquility Bay Beachfront Hotel and Resort](https://images.trvl-media.com/lodging/1000000/120000/117100/117099/854776a0_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### Tranquility Bay Beachfront Hotel and Resort

Save 100% on your flight

$1,202

per person

May 2 - May 7

found 1 day ago

Roundtrip flight included

Denver (DEN) to Miami (MIA)

8.8/10 Excellent! (1,000 reviews)

All 3 pools were beautiful, I loved the surrounding landscape. The two bedroom / 2.5 bath villa was wonderful. I loved sitting on the villas deck each morning to drink my coffee and enjoy the palm tree ocean view. The kitchen had everything we needed to make our meals! I would definitely recommend.

Reviewed on Mar 21, 2026

![Three Waters Resort and Marina, Islamorada, a Tribute Portfolio Resort](https://images.trvl-media.com/lodging/1000000/20000/11900/11864/4671ebc2_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

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

Save 100% on your flight

$764

per person

Jun 2 - Jun 6

found 16 hours ago

Roundtrip flight included

Chicago (ORD) to Miami (MIA)

9/10 Wonderful! (165 reviews)

No breakfast bar at this resort. Many onsite options for purchase. I did miss having a microwave.

Reviewed on Mar 27, 2026

![Cheeca Lodge & Spa](https://images.trvl-media.com/lodging/1000000/10000/5800/5780/4608d7e2_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### Cheeca Lodge & Spa

Matecumbe

Save 100% on your flight

$1,047

per person

Jun 4 - Jun 7

found 14 hours ago

Roundtrip flight included

Des Moines (DSM) to Miami (MIA)

9.2/10 Wonderful! (1,308 reviews)

From the moment we checked in with Jessica we knew we’d love Cheeca lodge. Great pools, fishing dock and rooms, along with the friendliest staff

Reviewed on Apr 1, 2026

Don't see what you're looking for?

See all available trips from Columbus to Florida Keys

[View all trips](https://expedia.com/go/package/search/FlightHotel/2026-05-02/2026-05-09/?FromAirport=Columbus,%20Ohio,%20United%20States%20of%20America&Destination=MIA&NumRoom=1&NumAdult=2&NumChild=0&paandie=true)

## 5\* Adventure vacations in Florida Keys

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

![Cheeca Lodge & Spa](https://images.trvl-media.com/lodging/1000000/10000/5800/5780/4608d7e2_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### Cheeca Lodge & Spa

Matecumbe

Save 100% on your flight

$1,047

per person

Jun 4 - Jun 7

found 14 hours ago

Roundtrip flight included

Des Moines (DSM) to Miami (MIA)

9.2/10 Wonderful! (1,308 reviews)

From the moment we checked in with Jessica we knew we’d love Cheeca lodge. Great pools, fishing dock and rooms, along with the friendliest staff

Reviewed on Apr 1, 2026

Don't see what you're looking for?

See all available trips from Columbus to Florida Keys

[View all trips](https://expedia.com/go/package/search/FlightHotel/2026-05-02/2026-05-09/?FromAirport=Columbus,%20Ohio,%20United%20States%20of%20America&Destination=MIA&NumRoom=1&NumAdult=2&NumChild=0&paandie=true)

## 3 Night Adventure vacations in Florida Keys

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

![Hawks Cay Resort](https://images.trvl-media.com/lodging/1000000/10000/6100/6068/8671ba74_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### Hawks Cay Resort

$551

per person

May 2 - May 5

found 1 day ago

Roundtrip flight included

Philadelphia (PHL) to Miami (MIA)

8/10 Very Good! (1,015 reviews)

Staff were friendly and helpful. My family enjoyed the pools and Lagoon. We also enjoyed the marina and the restaurants on the resort.

Reviewed on Mar 30, 2026

![La Siesta Resort & Villas](https://images.trvl-media.com/lodging/3000000/2480000/2477600/2477508/18023e21_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### La Siesta Resort & Villas

Matecumbe

Save 100% on your flight

$653

per person

Jun 2 - Jun 5

found 11 hours ago

Roundtrip non-stop flight included

Kansas City (MCI) to Miami (MIA)

8.8/10 Excellent! (1,004 reviews)

Staff was nice. The rooms are old. Not that clean. They need a coat of new paint too. The bathroom was dirty. The shuttle took 30 min and he didn't show up.

Reviewed on Apr 1, 2026

![Tranquility Bay Beachfront Hotel and Resort](https://images.trvl-media.com/lodging/1000000/120000/117100/117099/854776a0_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### Tranquility Bay Beachfront Hotel and Resort

Save 100% on your flight

$796

per person

Jun 4 - Jun 7

found 1 day ago

Roundtrip flight included

Houston (HOU) to Miami (MIA)

8.8/10 Excellent! (1,000 reviews)

All 3 pools were beautiful, I loved the surrounding landscape. The two bedroom / 2.5 bath villa was wonderful. I loved sitting on the villas deck each morning to drink my coffee and enjoy the palm tree ocean view. The kitchen had everything we needed to make our meals! I would definitely recommend.

Reviewed on Mar 21, 2026

Don't see what you're looking for?

See all available trips from Columbus to Florida Keys

[View all trips](https://expedia.com/go/package/search/FlightHotel/2026-05-02/2026-05-09/?FromAirport=Columbus,%20Ohio,%20United%20States%20of%20America&Destination=MIA&NumRoom=1&NumAdult=2&NumChild=0&paandie=true)

## 4 Night Adventure vacations in Florida Keys

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

![Hawks Cay Resort](https://images.trvl-media.com/lodging/1000000/10000/6100/6068/8671ba74_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### Hawks Cay Resort

Save 100% on your flight

$607

per person

May 3 - May 7

found 9 hours ago

Roundtrip flight included

Philadelphia (PHL) to Miami (MIA)

8/10 Very Good! (1,015 reviews)

Staff were friendly and helpful. My family enjoyed the pools and Lagoon. We also enjoyed the marina and the restaurants on the resort.

Reviewed on Mar 30, 2026

![Cheeca Lodge & Spa](https://images.trvl-media.com/lodging/1000000/10000/5800/5780/4608d7e2_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### Cheeca Lodge & Spa

Matecumbe

$1,007

per person

Jun 4 - Jun 8

found 19 hours ago

Roundtrip flight included

Philadelphia (PHL) to Miami (MIA)

9.2/10 Wonderful! (1,308 reviews)

From the moment we checked in with Jessica we knew we’d love Cheeca lodge. Great pools, fishing dock and rooms, along with the friendliest staff

Reviewed on Apr 1, 2026

![Tranquility Bay Beachfront Hotel and Resort](https://images.trvl-media.com/lodging/1000000/120000/117100/117099/854776a0_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### Tranquility Bay Beachfront Hotel and Resort

Save 100% on your flight

$920

per person

Jun 4 - Jun 8

found 1 day ago

Roundtrip non-stop flight included

Chicago (CHI) to Miami (MIA)

8.8/10 Excellent! (1,000 reviews)

All 3 pools were beautiful, I loved the surrounding landscape. The two bedroom / 2.5 bath villa was wonderful. I loved sitting on the villas deck each morning to drink my coffee and enjoy the palm tree ocean view. The kitchen had everything we needed to make our meals! I would definitely recommend.

Reviewed on Mar 21, 2026

Don't see what you're looking for?

See all available trips from Columbus to Florida Keys

[View all trips](https://expedia.com/go/package/search/FlightHotel/2026-05-02/2026-05-09/?FromAirport=Columbus,%20Ohio,%20United%20States%20of%20America&Destination=MIA&NumRoom=1&NumAdult=2&NumChild=0&paandie=true)

## Find awesome Florida Keys adventure vacations

####  How can I book the best Florida Keys adventure trips? 

Choose your own adventure in Florida Keys, whether that’s a white-knuckle experience or a weekend walk. Read the reviews of the adventures that have gone before to be sure your chosen stay is your idea of fun. 

####  How can I plan the perfect Florida Keys family adventure vacation? 

Adventure awaits when you select the family-friendly filter. There’s plenty of excitement for all ages in Florida Keys. Just make sure to check your chosen escapade is within the realms of can-do for the whole clan and will have the whole team grinning. 

####  Can I book all-inclusive Florida Keys adventure vacation packages? 

By refining your filters, you can explore all-amazing, all-adventurous, all-inclusive vacation packages. Amp up the extravagance with a few more filters too. Pick pristine pools, sensational spas, or wondrous waterparks for a sensational adventure getaway. 

####  Why should I book a Florida Keys adventure vacation for couples? 

Book a Florida Keys couples adventure vacation for the ultimate in romance and memory-making. Stunning scenery, heart-racing happenings, and the grandeur of the great outdoors—it’s the best way to bond. 

####  How can I find the best deals on adventure packages in Florida Keys? 

It’s easy to unleash fabulously affordable adventures. Enter the dates for your caper, then sort your search results by price or deals. 

####  Can I book an adventure vacation package in Florida Keys with free cancellation and/or flexible dates? 

Yes! When you’re searching for a great getaway, filter by payment option for free cancellation, so a change of plans won’t mess up your adventures. You’ll find buy now, pay later options, too, for full-on flexibility. 

####  Why should I book a Florida Keys adventure trip with Expedia? 

Adventure, airfare, accommodation, ATOL protection, and activities—all on one site. And that’s just the benefits that begin with A. 

## Top Adventure Florida Keys Hotels

![Southernmost Beach Resort and Guesthouses](https://images.trvl-media.com/lodging/1000000/870000/863400/863329/546caf1e_y.jpg?impolicy=resizecrop&rw=340&ch=150)

### 

Southernmost Beach Resort and Guesthouses

1319 Duval Street Key West FL

- 10 min walk from Duval Street

Book a stay at this beach hotel in Key West. Enjoy free WiFi, 3 outdoor pools, and a full-service spa. Our guests praise the pool and the helpful staff in our ...

8.8/10 Excellent! (3,171 reviews)

Clean and very friendly staff. Beach view adequate for side of building. Great breakfast variety. Overall, enjoyable experience.

Reviewed on Apr 1, 2026

[](https://expedia.com/Key-West-Hotels-Southernmost-Beach-Resort.h863329.Hotel-Information)

![Hawks Cay Resort](https://images.trvl-media.com/lodging/1000000/10000/6100/6068/8671ba74_y.jpg?impolicy=resizecrop&rw=340&ch=150)

### 

Hawks Cay Resort

61 Hawks Cay Blvd Marathon FL

- 2 hours drive from Duval Street

Book a stay at this luxury hotel in Marathon. Enjoy free WiFi, 5 outdoor pools, and a full-service spa. Our guests praise the pool and the helpful staff in our ...

8/10 Very Good! (1,010 reviews)

They dont strive to serve. Our room had a sliding bathroom door that did not lock or remain closed. It took them 3 days to fix it. The last day, the entire floor smelled fish. They sprayed copious amounts of air freshener but it didnt help. Overall, its a nice place with great views and amenities ...

Reviewed on Mar 31, 2026

[](https://expedia.com/Marathon-Hotels-Hawks-Cay-Resort.h6068.Hotel-Information)

![Cheeca Lodge & Spa](https://images.trvl-media.com/lodging/1000000/10000/5800/5780/4608d7e2_y.jpg?impolicy=resizecrop&rw=340&ch=150)

### 

Cheeca Lodge & Spa

81801 Overseas Highway, Mile Marker 82 Islamorada FL

- 3 hours drive from Duval Street

Book a stay at this luxury resort in Islamorada. Enjoy free parking, 3 outdoor pools, and a full-service spa. Our guests praise the pool and the helpful staff ...

9.2/10 Wonderful! (1,308 reviews)

From the moment we checked in with Jessica we knew we’d love Cheeca lodge. Great pools, fishing dock and rooms, along with the friendliest staff

Reviewed on Apr 1, 2026

[](https://expedia.com/Islamorada-Hotels-Cheeca-Lodge-Spa.h5780.Hotel-Information)

[See all 8,081 properties in Florida Keys](https://expedia.com/Hotel-Search?rfrrid=TG.LP.Hotels.Package&regionId=6023765)

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.

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## More Vacation Ideas

[Flights to Florida Keys

](https://expedia.com/Cheap-Flights-To-Florida-Keys.d6023765.Travel-Guide-Flights)[

Florida Keys Hotels

](https://expedia.com/Florida-Keys-Hotels.d6023765.Travel-Guide-Hotels)[

Vacation Rentals in Florida Keys

](https://expedia.com/Florida-Keys-Vacation-Rentals.d6023765.Travel-Guide-VacationRentals)[

Car Rentals in Florida Keys

](https://expedia.com/Car-Rentals-In-Florida-Keys.d6023765.Car-Rental-Guide)[

Florida Keys Vacations

](https://expedia.com/Florida-Keys.d6023765.Destination-Travel-Guides)[

Things to do in Florida Keys

](https://expedia.com/Things-To-Do-In-Florida-Keys.d6023765.Travel-Guide-Activities)

\* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.

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