Title: Adventure Vacations in Florida Keys 2026/2026 | Expedia.ca

![](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

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## Flight and Adventure hotel deals in Florida Keys

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

![Blue Flamingo Resort Key West](https://images.trvl-media.com/lodging/13000000/12600000/12599300/12599231/c4b850d1_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### Blue Flamingo Resort Key West

New Town

CA $1,540

per person

Feb 5 - Feb 8

found 22 hours ago

Roundtrip non-stop flight included

Montreal (YMQ) to Key West (EYW)

8/10 Very Good! (1,693 reviews)

Love this place rooms are wonderful pool view is great. Employees all speak English and are so nice and helpful. Especially Flora

Reviewed on Dec 5, 2025

![Hawks Cay Resort](https://images.trvl-media.com/lodging/1000000/10000/6100/6068/b1845555_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### Hawks Cay Resort

CA $2,505

per person

Feb 7 - Feb 14

found 20 hours ago

Roundtrip flight included

Toronto (YYZ) to Miami (MIA)

8/10 Very Good! (1,003 reviews)

Everything in this island is perfect and amazing.

Reviewed on Dec 5, 2025

![Tranquility Bay Beachfront Hotel and Resort](https://images.trvl-media.com/lodging/1000000/120000/117100/117099/2efaf74f_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### Tranquility Bay Beachfront Hotel and Resort

CA $2,905

per person

Feb 7 - Feb 14

found 20 hours ago

Roundtrip flight included

Toronto (YYZ) to Miami (MIA)

8.8/10 Excellent! (1,003 reviews)

The place was great and appropriately named because it was very tranquil and relaxing. The only disappointment was that there is no spa facility and breakfast available only in your room.

Reviewed on Nov 27, 2025

![La Siesta Resort & Villas](https://images.trvl-media.com/lodging/3000000/2480000/2477600/2477508/eda54a36_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### La Siesta Resort & Villas

Matecumbe

CA $1,949

per person

Jan 4 - Jan 11

found 19 hours ago

Roundtrip non-stop flight included

Toronto (YTO) to Miami (MIA)

8.6/10 Excellent! (1,000 reviews)

Great stay and beautiful space

Reviewed on Dec 1, 2025

![Faro Blanco Resort & Yacht Club Marathon, Curio by Hilton](https://images.trvl-media.com/lodging/2000000/1170000/1169600/1169583/16bbce87_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### Faro Blanco Resort & Yacht Club Marathon, Curio by Hilton

CA $2,108

per person

Feb 7 - Feb 14

found 20 hours ago

Roundtrip flight included

Toronto (YYZ) to Miami (MIA)

8.8/10 Excellent! (1,275 reviews)

Stayed 3 nights. The room was cleaned after the 1st night. After the second night the room was not touched. Went to front desk to get fresh to towels and told they would clean the room the next day. came back on the 3rd day and the room was not touched again.

Reviewed on Nov 23, 2025

Don't see what you're looking for?

See all available trips from Columbus to Florida Keys

[View all trips](https://expedia.ca/go/package/search/FlightHotel/2026-01-05/2026-01-12/?FromAirport=Columbus,%20Ohio,%20United%20States%20of%20America&Destination=MIA&NumRoom=1&NumAdult=2&NumChild=0&paandie=true)

## 5\* Adventure holidays in Florida Keys

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

![Cheeca Lodge & Spa](https://images.trvl-media.com/lodging/1000000/10000/5800/5780/617c0723_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### Cheeca Lodge & Spa

Matecumbe

CA $1,167

per person

Jan 4 - Jan 7

found 1 day ago

Roundtrip flight included

Toronto (YTO) to Miami (MIA)

9.2/10 Wonderful! (1,262 reviews)

Summary great location, great vibes just a little older so be prepared for less than perfect. Great location, great view of the sunrise. Property gives a feeling that a lot of people are regulars and have been going there for a long time with extended family holiday vibes. The property itself is older and a little tatty around the edges please don’t let that put you off it’s a great spot. The Atlantic’s edge restaurant isn’t great I had a steak and it was the toughest fattiest piece of steak I think I’ve ever experienced. The second night we went to the beach cafe off site for dinner which was great and offered a lovely beach to watch the sunset.

Reviewed on Dec 4, 2025

Don't see what you're looking for?

See all available trips from Columbus to Florida Keys

[View all trips](https://expedia.ca/go/package/search/FlightHotel/2026-01-05/2026-01-12/?FromAirport=Columbus,%20Ohio,%20United%20States%20of%20America&Destination=MIA&NumRoom=1&NumAdult=2&NumChild=0&paandie=true)

## 3 Night Adventure holidays 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/b1845555_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### Hawks Cay Resort

CA $1,007

per person

Jan 4 - Jan 7

found 1 day ago

Roundtrip flight included

Toronto (YTO) to Miami (MIA)

8/10 Very Good! (1,003 reviews)

Everything in this island is perfect and amazing.

Reviewed on Dec 5, 2025

![Blue Flamingo Resort Key West](https://images.trvl-media.com/lodging/13000000/12600000/12599300/12599231/c4b850d1_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### Blue Flamingo Resort Key West

New Town

CA $1,540

per person

Feb 5 - Feb 8

found 22 hours ago

Roundtrip non-stop flight included

Montreal (YMQ) to Key West (EYW)

8/10 Very Good! (1,693 reviews)

Love this place rooms are wonderful pool view is great. Employees all speak English and are so nice and helpful. Especially Flora

Reviewed on Dec 5, 2025

![Tranquility Bay Beachfront Hotel and Resort](https://images.trvl-media.com/lodging/1000000/120000/117100/117099/2efaf74f_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### Tranquility Bay Beachfront Hotel and Resort

CA $1,216

per person

Jan 4 - Jan 7

found 1 day ago

Roundtrip flight included

Toronto (YTO) to Miami (MIA)

8.8/10 Excellent! (1,003 reviews)

The place was great and appropriately named because it was very tranquil and relaxing. The only disappointment was that there is no spa facility and breakfast available only in your room.

Reviewed on Nov 27, 2025

Don't see what you're looking for?

See all available trips from Columbus to Florida Keys

[View all trips](https://expedia.ca/go/package/search/FlightHotel/2026-01-05/2026-01-12/?FromAirport=Columbus,%20Ohio,%20United%20States%20of%20America&Destination=MIA&NumRoom=1&NumAdult=2&NumChild=0&paandie=true)

## 4 Night Adventure holidays 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/b1845555_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### Hawks Cay Resort

CA $1,380

per person

Jan 17 - Jan 21

found 1 day ago

Roundtrip non-stop flight included

Montreal (YUL) to Miami (MIA)

8/10 Very Good! (1,003 reviews)

Everything in this island is perfect and amazing.

Reviewed on Dec 5, 2025

![Blue Flamingo Resort Key West](https://images.trvl-media.com/lodging/13000000/12600000/12599300/12599231/c4b850d1_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### Blue Flamingo Resort Key West

New Town

CA $1,742

per person

Feb 15 - Feb 19

found 1 hour ago

Roundtrip non-stop flight included

Toronto (YYZ) to Key West (EYW)

8/10 Very Good! (1,693 reviews)

Love this place rooms are wonderful pool view is great. Employees all speak English and are so nice and helpful. Especially Flora

Reviewed on Dec 5, 2025

![Tranquility Bay Beachfront Hotel and Resort](https://images.trvl-media.com/lodging/1000000/120000/117100/117099/2efaf74f_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### Tranquility Bay Beachfront Hotel and Resort

CA $1,782

per person

Jan 19 - Jan 23

found 14 hours ago

Roundtrip flight included

Regina (YQR) to Miami (MIA)

8.8/10 Excellent! (1,003 reviews)

The place was great and appropriately named because it was very tranquil and relaxing. The only disappointment was that there is no spa facility and breakfast available only in your room.

Reviewed on Nov 27, 2025

Don't see what you're looking for?

See all available trips from Columbus to Florida Keys

[View all trips](https://expedia.ca/go/package/search/FlightHotel/2026-01-05/2026-01-12/?FromAirport=Columbus,%20Ohio,%20United%20States%20of%20America&Destination=MIA&NumRoom=1&NumAdult=2&NumChild=0&paandie=true)

## Adventure Hotels in Florida Keys

![Southernmost Beach Resort and Guesthouses](https://images.trvl-media.com/lodging/1000000/870000/863400/863329/026f10af_y.jpg?impolicy=resizecrop&rw=340&ch=150)

### 

Southernmost Beach Resort and Guesthouses

1319 Duval Street Key West FL

- 11 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 ...

8.6/10 Excellent! (2,907 reviews)

Clean room. Staff was friendly pool and beach were great

Reviewed on Dec 1, 2025

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

![Hawks Cay Resort](https://images.trvl-media.com/lodging/1000000/10000/6100/6068/b1845555_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! (1,009 reviews)

Rooms were clean

Reviewed on Dec 1, 2025

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

![Cheeca Lodge & Spa](https://images.trvl-media.com/lodging/1000000/10000/5800/5780/617c0723_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 ...

9/10 Wonderful! (1,278 reviews)

Property is beautiful with tons of amenities. The room was very nice and overall we were very happy. Here are a few of the issues we had though for full transparency. The beach is sand, but it's hard in a way that's a bit unnatural and doesn't flow into the water. There were weddings on two nights ...

Reviewed on Dec 3, 2025

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

[See all 8,400 properties in Florida Keys](https://expedia.ca/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 Vacations Ideas

[Flights to Florida Keys

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

Florida Keys Hotels

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

Florida Keys Vacation Rentals

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

Florida Keys Car Rentals

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

Florida Keys Vacations

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

Things to do in Florida Keys

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

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