Title: Rockland Key Vacation Packages & Trips 2026 from CA $1,281 | Expedia.ca

[Rockland Key Travel Guide](https://expedia.ca/Rockland-Key.dx553248635976197596)[Hotels in Rockland Key](https://expedia.ca/Rockland-Key-Hotels.d553248635976197596.Travel-Guide-Hotels)[Vacation Rentals in Rockland Key](https://expedia.ca/Rockland-Key-Vacation-Rentals.d553248635976197596.Travel-Guide-VacationRentals)[Flights to Rockland Key](https://expedia.ca/Cheap-Flights-To-Rockland-Key.d553248635976197596.Travel-Guide-Flights)[Rockland Key Car Rentals](https://expedia.ca/Car-Rentals-In-Rockland-Key.d553248635976197596.Car-Rental-Guide)

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# Rockland Key Vacation Packages

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

- ##  
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Better together  
Save up to CA $1,096 when you book a flight and hotel together\*
- ###  
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With over 300,000 hotels worldwide, it's easy to create a perfect package
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## Top Rockland Key Vacation Deals

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

![Hyatt Vacation Club at Beach House, Key West](https://images.trvl-media.com/lodging/1000000/860000/858000/857962/fc0a2a7e_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### Hyatt Vacation Club at Beach House, Key West

CA $1,281

per person

Feb 26 - Mar 1

found 21 hours ago

Roundtrip non-stop flight included

Detroit (DTW) to Key West (EYW)

9.4/10 Exceptional! (1,002 reviews)

Found a roach in room

Reviewed on Dec 14, 2025

![The Key West Hotel](https://images.trvl-media.com/lodging/9000000/8660000/8657100/8657021/bc64cbf7_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### The Key West Hotel

Key West Historic District

CA $2,238

per person

Feb 26 - Mar 1

found 9 hours ago

Roundtrip non-stop flight included

Detroit (DTW) to Key West (EYW)

9.2/10 Wonderful! (505 reviews)

Being right on Duval Street if city noise bothers you you might want to stay a block or two off Duval. But if you want all the action then this place is fantastic. Staff is great and the room was nicely appointed and very comfortable.

Reviewed on Dec 12, 2025

![Ella's Cottages - Key West Historic Inns](https://images.trvl-media.com/lodging/1000000/870000/863200/863188/deb4f031_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### Ella's Cottages - Key West Historic Inns

Old Town Key West

CA $2,587

per person

Jan 15 - Jan 18

found 1 day ago

Roundtrip non-stop flight included

Detroit (DTW) to Key West (EYW)

9.4/10 Exceptional! (390 reviews)

The cottage was perfect, centrally located and a wonderful place to stay!

Reviewed on Dec 13, 2025

![Lighthouse Hotel - Key West Historic Inns](https://images.trvl-media.com/lodging/2000000/1180000/1171100/1171079/2155599f_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### Lighthouse Hotel - Key West Historic Inns

Old Town Key West

CA $1,821

per person

Feb 26 - Mar 1

found 21 hours ago

Roundtrip non-stop flight included

Detroit (DTW) to Key West (EYW)

9/10 Wonderful! (831 reviews)

Property was beautiful. Beds so comfy! Loved watching the cats at The Hemingway House across the street. Close cafe, restaurant and bars within 3 minute walk. Lush gardens surrounds the property and pool/dinning area. We stayed in the Snowhite Suite, 1st floor. Had a private patio, separate living room and huge bathroom. Great space for 2-3 people. We look forward to coming back.

Reviewed on Dec 14, 2025

![Hyatt Vacation Club at Windward Pointe, Key West](https://images.trvl-media.com/lodging/1000000/870000/868700/868697/481a771e_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### Hyatt Vacation Club at Windward Pointe, Key West

CA $1,360

per person

Feb 26 - Mar 1

found 21 hours ago

Roundtrip non-stop flight included

Detroit (DTW) to Key West (EYW)

9.6/10 Exceptional! (1,002 reviews)

Excellent place to stay on Key West, spacious apartment, nice view, quiet area, great pool area and billiard table, mini market inside property. Just 10 min drive to famous Duvall Street and different restaurants walking distance from the hotel.

Reviewed on Dec 15, 2025

## Ready to book your vacation to Rockland Key?

Choose your dates

## Rockland Key Hotel Deals

![Beachside Resort & Residences](https://images.trvl-media.com/lodging/1000000/30000/25900/25865/290b242a_y.jpg?impolicy=resizecrop&rw=340&ch=150)

### 

Beachside Resort & Residences

3841 N Roosevelt Blvd Key West FL

Fully refundableReserve now, pay when you stay

CA $218

CA $315 total

Dec 16 - Dec 17

includes taxes & fees

8.6/10 Excellent! (1,765 reviews)

The pool beach area was clean, water in pool and hot tub clean and warm Shuttle to Duvall street was very convent and helpful to get to shopping / dinning area

Reviewed on Dec 12, 2025

[](https://expedia.ca/Hotel-Search?startDate=16%2F12%2F2025&endDate=17%2F12%2F2025&selected=25865&PinnedHotelID=25865&HadPinnedHotel=true&regionId=553248635976197596)

![Blue Flamingo Resort Key West](https://images.trvl-media.com/lodging/13000000/12600000/12599300/12599231/c4b850d1_y.jpg?impolicy=resizecrop&rw=340&ch=150)

### 

Blue Flamingo Resort Key West

3820 North Roosevelt Boulevard Key West FL

Fully refundableReserve now, pay when you stay

CA $160

CA $257 total

Dec 18 - Dec 19

includes taxes & fees

8/10 Very Good! (1,752 reviews)

Nice resort with warm pool, two bars, Starbucks. Rooms clean

Reviewed on Dec 9, 2025

[](https://expedia.ca/Hotel-Search?startDate=18%2F12%2F2025&endDate=19%2F12%2F2025&selected=12599231&PinnedHotelID=12599231&HadPinnedHotel=true&regionId=553248635976197596)

![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

Fully refundable

CA $259

CA $392 total

Dec 18 - Dec 19

includes taxes & fees

8.6/10 Excellent! (2,933 reviews)

Beach and pool - bar, music and great staff

Reviewed on Dec 14, 2025

[](https://expedia.ca/Hotel-Search?startDate=18%2F12%2F2025&endDate=19%2F12%2F2025&selected=863329&PinnedHotelID=863329&HadPinnedHotel=true&regionId=553248635976197596)

[See all 3,394 properties in Rockland Key](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Package&startDate=16%2F12%2F2025&endDate=17%2F12%2F2025&regionId=553248635976197596)

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.

![](https://forever.travel-assets.com/flex/flexmanager/images/2022/06/08/all-inclusive_holidays_US.jpeg?impolicy=fcrop&w=300&h=300&q=mediumHigh)

All Inclusive Vacations

[](https://expedia.ca/lp/theme-vacations/all-inclusive-vacations?rfrr=editorial.All_Inclusive%20Vacations.click)

![](https://forever.travel-assets.com/flex/flexmanager/images/2022/10/17/XPC_Beach_Overview_HR_v3.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh)

Beach Vacations

[](https://expedia.ca/lp/theme-vacations/beach-vacations?rfrr=editorial.Beach_Vacations.click)

![](https://forever.travel-assets.com/flex/flexmanager/images/2022/06/08/Family_holidays_US_3_.jpeg?impolicy=fcrop&w=300&h=300&q=mediumHigh)

Family Vacations

[](https://expedia.ca/lp/theme-vacations/kid-friendly-vacations?rfrr=editorial.Family_Vacations.click)

![](https://forever.travel-assets.com/flex/flexmanager/images/2022/04/29/frCA_Sejours_golf-Portugal.jpeg?impolicy=fcrop&w=300&h=300&q=mediumHigh)

Golf Vacations

[](https://expedia.ca/lp/theme-vacations/golf-vacations?rfrr=editorial.Golf_Vacations.click)

![](https://forever.travel-assets.com/flex/flexmanager/images/2022/07/15/US_Luxury_VR_Miami.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh)

Luxury Vacations

[](https://expedia.ca/lp/theme-vacations/luxury-vacations?rfrr=editorial.Luxury_Vacations.click)

![](https://forever.travel-assets.com/flex/flexmanager/images/2022/08/29/romantic.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh)

Romantic Vacations

[](https://expedia.ca/lp/theme-vacations/romantic-vacations?rfrr=editorial.Romantic_Vacations.click)

![](https://forever.travel-assets.com/flex/flexmanager/images/2022/10/17/31952_v1_atfraraski22_insta_4.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh)

Ski Vacations

[](https://expedia.ca/lp/theme-vacations/ski-vacations?rfrr=editorial.Ski_Vacations.click)

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- [Raccoon Key Vacation Rentals ](https://www.expedia.ca/Raccoon-Key-Vacation-Rentals.d180164.Travel-Guide-VacationRentals)

- [Things to do in Big Coppitt Key ](https://www.expedia.ca/Things-To-Do-In-Big-Coppitt-Key.d553248635975850102.Travel-Guide-Activities)
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- [Things to do in Stock Island ](https://www.expedia.ca/Things-To-Do-In-Stock-Island.d180166.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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