Title: Rockland Key Vacation Packages & Trips 2026 from CA $1,936 | 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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## 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 $1,936

per person

Feb 25 - Mar 4

found 13 hours ago

Roundtrip flight included

Detroit (DTW) to Key West (EYW)

9.4/10 Exceptional! (1,002 reviews)

This resort is perfect for a family. The rooms have full kitchens, two full bathroom as well as a pull-out sofa. The room was recently renovated and luxurious with a giant shower in the master. The pool was not busy when we were there even though it was over New Years. My daughter was able to swim everyday and we could read by the pool- it was quiet and perfect. We ordered snacks and lunch from the tiki bar and they were great! Each room has a screened in porch as well which is gear in the AM and evening. There are some small biting bugs. The evening so be careful on evening swims. The screen room helps with this! We were told there was a contextual breakfast on Mondays only. We went down for it and the front desk said there wasn’t one that week…that was the only thing that was off from our stay.

Reviewed on Jan 12, 2026

![Oceans Edge Key West Resort, Hotel & Marina](https://images.trvl-media.com/lodging/17000000/16210000/16203000/16202992/f7424907_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### Oceans Edge Key West Resort, Hotel & Marina

CA $2,163

per person

Feb 25 - Mar 4

found 13 hours ago

Roundtrip flight included

Detroit (DTW) to Key West (EYW)

9/10 Wonderful! (1,736 reviews)

The staff that cleaned our room were great! Kept everything fresh and clean for our entire stay!

Reviewed on Jan 12, 2026

![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 $4,056

per person

Feb 14 - Feb 20

found 1 day 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

![The Perry Hotel & Marina Key West](https://images.trvl-media.com/lodging/18000000/17320000/17313700/17313680/e4eb7fd5_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### The Perry Hotel & Marina Key West

CA $2,200

per person

Feb 25 - Mar 4

found 13 hours ago

Roundtrip flight included

Detroit (DTW) to Key West (EYW)

9.4/10 Exceptional! (1,151 reviews)

All staff were wonderful, especially the concierge. I also loved the ease of using the shuttle to get to the Old town. Everything was clean and comfortable. The room was actually spacious as well.

Reviewed on Jan 13, 2026

![Southernmost Beach Resort and Guesthouses](https://images.trvl-media.com/lodging/1000000/870000/863400/863329/026f10af_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### Southernmost Beach Resort and Guesthouses

Old Town Key West

CA $3,762

per person

Feb 14 - Feb 20

found 1 day ago

Roundtrip non-stop flight included

Detroit (DTW) to Key West (EYW)

8.6/10 Excellent! (2,844 reviews)

Room smelled musty all the time we were there and we ran the ac all the time. Also, breakfast was not served at guesthouse so we had to walk to main building every day. Not a big deal but it was not what we were told when we booked our stay. Otherwise, it was a very pleasant stay, all in all

Reviewed on Jan 12, 2026

## 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 $352

CA $466 total

Jan 14 - Jan 15

includes taxes & fees

8.6/10 Excellent! (1,885 reviews)

Room was very clean and for someone like me who is OCD about staying somewhere clean i was very comfortable there would definitely come back !!!

Reviewed on Jan 9, 2026

[](https://expedia.ca/Hotel-Search?startDate=14%2F01%2F2026&endDate=15%2F01%2F2026&selected=25865&PinnedHotelID=25865&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 $631

CA $812 total

Jan 14 - Jan 15

includes taxes & fees

8.6/10 Excellent! (2,987 reviews)

Chair availability was a problem

Reviewed on Jan 7, 2026

[](https://expedia.ca/Hotel-Search?startDate=14%2F01%2F2026&endDate=15%2F01%2F2026&selected=863329&PinnedHotelID=863329&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 $336

CA $456 total

Jan 14 - Jan 15

includes taxes & fees

8/10 Very Good! (1,833 reviews)

Great room, great staff

Reviewed on Jan 8, 2026

[](https://expedia.ca/Hotel-Search?startDate=14%2F01%2F2026&endDate=15%2F01%2F2026&selected=12599231&PinnedHotelID=12599231&HadPinnedHotel=true&regionId=553248635976197596)

[See all 3,384 properties in Rockland Key](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Package&startDate=14%2F01%2F2026&endDate=15%2F01%2F2026&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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- [Auto Rent Rental Cars in Boca Chica Key ](https://www.expedia.ca/Auto-Rent-Car-Rentals-In-Boca-Chica-Key.d553248635083916609-c1006.Car-Rental-Guide-Suppliers)
- [Car rentals near Boca Chica Key ](https://www.expedia.ca/Car-Rentals-In-Boca-Chica-Key.d553248635083916609.Car-Rental-Guide)
- [Click & Rent Rental Cars in Key Haven ](https://www.expedia.ca/Click-Rent-Car-Rentals-In-Key-Haven.d553248635976197997-c1089.Car-Rental-Guide-Suppliers)
- [Easirent Rental Cars in Key Haven ](https://www.expedia.ca/Easirent-Car-Rentals-In-Key-Haven.d553248635976197997-c1039.Car-Rental-Guide-Suppliers)

- [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)
- [Things to do in Boca Chica Key ](https://www.expedia.ca/Things-To-Do-In-Boca-Chica-Key.d553248635083916609.Travel-Guide-Activities)
- [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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