Name: Southernmost Beach Resort and Guesthouses
Price range: CA $289
Rating: 8.8

Top Holiday Package Deals in Beachside

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

Winslow's Bungalows - Key West Historic Inns

Old Town Key West

CA $2,013

per person

Jul 16 - Jul 23

found 1 day ago

Roundtrip non-stop flight included

Halifax (YHZ) to Key West (EYW)

9.2/10 Wonderful! (1,267 reviews)

Great stay. Little gem that feels like home. Casual accommodations that fit perfectly for a trip to paradise. Two free drinks when you check in, SOLD. Will definitely return.

Reviewed on May 12, 2026

The Key West Hotel

Key West Historic District

CA $2,907

per person

Jul 16 - Jul 23

found 1 day ago

Roundtrip non-stop flight included

Halifax (YHZ) 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

Hyatt Vacation Club at Windward Pointe, Key West

CA $2,149

per person

Jun 15 - Jun 22

found 1 day ago

Roundtrip non-stop flight included

Hamilton (YHM) to Key West (EYW)

9.4/10 Exceptional! (1,066 reviews)

The property staff wasn’t as attentive as I would have hoped at a resort like this. The rooms were spacious and clean.

Reviewed on May 12, 2026

The Gardens Hotel

Old Town Key West

CA $2,928

per person

Jul 16 - Jul 23

found 1 day ago

Roundtrip non-stop flight included

Halifax (YHZ) to Key West (EYW)

9.8/10 Exceptional! (1,001 reviews)

I have rarely been so positively surprised by a hotel. The outdoor areas (pool, gardens, bar) were more spacious than I expected, and impeccably maintained. It is so tranquil and peaceful, yet so close to the action. The Master Suite was super nice - large balcony, private sauna, and 2 bathrooms. Would definitely come back.

Reviewed on May 14, 2026

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

Key West Historic District

CA $2,718

per person

Jun 29 - Jul 4

found 1 day ago

Roundtrip non-stop flight included

Toronto (YTO) to Key West (EYW)

No reviews

Where to stay in Beachside

Find the best Beachside areas and neighborhoods for the activities you enjoy most. Learn more about Beachside

Old Town Key West

3 out of top 10 points of interest in this area

3.5/5(8 area reviews)

Old Town, the historic heart of Key West, boasts a central business district and numerous tourist attractions. Explore the Key West Aquarium, Ernest Hemingway House, Mallory Square, and more in this vibrant area.

Key West Historic District

2 out of top 10 points of interest in this area

4.5/5(157 area reviews)

Old Town Key West boasts a rich history with 2485 historic buildings, and is home to popular attractions like Ernest Hemingway House and Mallory Square. Enjoy the lively atmosphere in the central business district.

Beachside Hotel Deals

Atlantic Paradise by AvantStay | Great Location w/ & Shared Pool and hot tub!

Key West FL

9.6/10 Exceptional! (91 reviews)

Great location. Great communication with owner.

Reviewed on Apr 17, 2026

Get rates

Blue Flamingo Resort Key West

3820 North Roosevelt Boulevard Key West FL

Fully refundableReserve now, pay when you stay

CA $207

CA $310 total

Jun 3 - Jun 4

includes taxes & fees

8.4/10 Very Good! (2,222 reviews)

Room was filthy

Reviewed on May 15, 2026

Southernmost Beach Resort and Guesthouses

1319 Duval Street Key West FL

Fully refundable

CA $289

CA $425 total

Jun 9 - Jun 10

includes taxes & fees

8.8/10 Excellent! (3,315 reviews)

Great Atmosphere and friendly staff

Reviewed on May 14, 2026

See all 2,804 properties in Beachside

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.