Name: Southernmost Beach Resort and Guesthouses
Price range: CA $299
Rating: 8.8

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 $1,562

per person

Jul 3 - Jul 7

found 1 day ago

Roundtrip non-stop flight included

Detroit (DTW) to Key West (EYW)

9.4/10 Exceptional! (1,066 reviews)

The hidden resort fees were absolutely ridiculous! $40 a day, plus $5 a day plus $150 coverage without any explanation. This property is located directly next to the airport and they do not provide a shuttle service to pick you up. We used Uber for everything, another extra expense. ( The Hampton Inn next door had a shuttle that went everywhere)

Reviewed on May 5, 2026

The Key West Hotel

Key West Historic District

CA $2,290

per person

Jun 27 - Jul 2

found 1 day ago

Roundtrip non-stop flight included

Toronto (YTO) to Key West (EYW)

9.2/10 Wonderful! (552 reviews)

The staff at the hotel were excellent. Very friendly and helpful. Room was very clean and comfortable. We were right in the middle of the old district which had many many places to explore. Hotel had a wonderful hidden pool with live music/bar next to it in case we just wanted to relax after exploring all day.

Reviewed on Apr 21, 2026

Paradise Place by Avantstay Key West Old Town Condo w/ Shared Pool

Key West Historic District

CA $2,971

per person

Jun 30 - Jul 5

found 6 hours ago

Roundtrip flight included

Toronto (YTO) to Key West (EYW)

No reviews

Hyatt Vacation Club at Beach House, Key West

CA $2,216

per person

Jun 27 - Jul 2

found 1 day ago

Roundtrip non-stop flight included

Toronto (YTO) to Key West (EYW)

9.4/10 Exceptional! (1,034 reviews)

Nice to have laundry in the apartment

Reviewed on May 7, 2026

Hyatt Vacation Club at Sunset Harbor, Key West

Old Town Key West

CA $1,795

per person

Jul 6 - Jul 10

found 1 day ago

Roundtrip non-stop flight included

Toronto (YTO) to Key West (EYW)

8.6/10 Excellent! (366 reviews)

Stayed in a one bedroom unit. Good size kitchen/living room, however bathroom was tiny. Bedroom was ok.. lots of closet/storage, however bed could have been bigger. Location was awesome… just a couple blocks to everything!

Reviewed on May 6, 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 $220

CA $325 total

May 25 - May 26

includes taxes & fees

8.4/10 Very Good! (2,212 reviews)

Was probably one of our favorite hotels in the keys definitely coming back

Reviewed on May 10, 2026

Margaritaville Beach House Key West

2001 South Roosevelt Boulevard Key West FL

Fully refundableReserve now, pay when you stay

CA $269

CA $389 total

Jun 8 - Jun 9

includes taxes & fees

8.8/10 Excellent! (1,812 reviews)

Staff was very helpful with all our needs. I would only recommend that the hot tub had hot water. It was cold and the jets were weak. Otherwise it was a perfect spot for us. We will be back.

Reviewed on May 7, 2026

Southernmost Beach Resort and Guesthouses

1319 Duval Street Key West FL

Fully refundable

CA $299

CA $436 total

May 25 - May 26

includes taxes & fees

8.8/10 Excellent! (3,293 reviews)

Amazing beach access, multiple pools, great food and bar options. Staff was exceptionally friendly and helpful. I would definitely stay there again.

Reviewed on May 9, 2026

See all 3,307 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.