Name: Beachside Resort & Residences
Price range: CA $384
Rating: 8.6

Top Rockland Key Vacation Deals

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

Hyatt Vacation Club at Windward Pointe, Key West

CA $1,868

per person

May 25 - May 29

found 1 day ago

Roundtrip non-stop flight included

Toronto (YTO) to Key West (EYW)

9.4/10 Exceptional! (1,020 reviews)

Everything was clean in the room just a bit outdated, the rooms probably could use some updating. However, the pool area and grounds were absolutely beautiful. I would stay again just for the grounds and pool. It is next to the airport so during the day there are a lot of planes going out with some flight noise.

Reviewed on Mar 24, 2026

The Key West Hotel

Key West Historic District

CA $2,201

per person

May 25 - May 29

found 1 day ago

Roundtrip non-stop flight included

Toronto (YTO) to Key West (EYW)

9.2/10 Wonderful! (536 reviews)

Love this place! Perfect location, nice rooms and cool bar with live music every night on site!

Reviewed on Mar 17, 2026

Fitch Lodge - Key West Historic Inns

Key West Historic District

CA $1,876

per person

May 5 - May 12

found 1 day ago

Roundtrip non-stop flight included

Toronto (YTO) to Key West (EYW)

8.8/10 Excellent! (575 reviews)

Great location, friendly staff, and plenty of amenities.

Reviewed on Mar 23, 2026

Winslow's Bungalows - Key West Historic Inns

Old Town Key West

CA $2,517

per person

May 5 - May 12

found 1 day ago

Roundtrip non-stop flight included

Toronto (YTO) to Key West (EYW)

9.2/10 Wonderful! (1,194 reviews)

Property was immaculate, staff is so friendly and goes out of their way to make sure you have everything you need. Walking distance to Duval, Southernmost point and Sunset Pier. Amenities are top notch. Can't say enough about how much we enjoyed our stay! 20 out of 10!

Reviewed on Mar 24, 2026

The Gardens Hotel

Old Town Key West

CA $2,753

per person

May 5 - May 12

found 1 day ago

Roundtrip non-stop flight included

Toronto (YTO) to Key West (EYW)

9.8/10 Exceptional! (1,000 reviews)

A little slice of heaven nestled amongst quaint downtown location. Quiet and relaxing atmosphere perfect Key West getaway.

Reviewed on Mar 21, 2026

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Rockland Key Hotel Deals

Blue Flamingo Resort Key West

3820 North Roosevelt Boulevard Key West FL

Fully refundableReserve now, pay when you stay

CA $357

CA $479 total

Apr 19 - Apr 20

includes taxes & fees

8.2/10 Very Good! (1,992 reviews)

Everything was

Reviewed on Mar 24, 2026

Margaritaville Beach House Key West

2001 South Roosevelt Boulevard Key West FL

Fully refundableReserve now, pay when you stay

CA $443

CA $587 total

Apr 20 - Apr 21

includes taxes & fees

8.8/10 Excellent! (1,799 reviews)

The worst experience I have ever had in any resort. The staff needs some lessons in manners! I wasn’t even asked how my day was when I was checking out! The room was the worst experience bathroom handle falling off every time I open the door. Noisy elevator sounds old, worn out furniture, just a ...

Reviewed on Mar 24, 2026

Beachside Resort & Residences

3841 N Roosevelt Blvd Key West FL

Fully refundableReserve now, pay when you stay

CA $384

CA $564 total

Mar 25 - Mar 26

includes taxes & fees

8.6/10 Excellent! (2,089 reviews)

Shuttle times are extremely accurate. Beautfil place with friendly staff. Only wish checkout time was a bit later. Elevators were out our entire stay. We were on third floor. The staff did offer to help carry our luggage up.

Reviewed on Mar 22, 2026

See all 3,317 properties in Rockland Key

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.