Name: Southernmost Beach Resort and Guesthouses
Price range: $258 total
Rating: 8.6

Plan, book, travel with confidence

Better together

Save up to $1,045 when you book a flight and hotel together*

Find the right fit

With over 300,000 hotels worldwide, it's easy to create a perfect package

Rest easy

Plan, book, and manage your trip all in one place

The Latest Rockland Key vacation packages

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

Oceans Edge Key West Resort, Hotel & Marina

Save 100% on your flight

$596

per person

Nov 10 - Nov 14

found 1 day ago

Roundtrip non-stop flight included

Boston (BOS) to Key West (EYW)

9/10 Wonderful! (1,722 reviews)

Very good for visiting

Reviewed on Sep 27, 2025

Lighthouse Hotel - Key West Historic Inns

Old Town Key West

Save 100% on your flight

$667

per person

Dec 12 - Dec 15

found 1 day ago

Roundtrip non-stop flight included

Boston (BOS) to Key West (EYW)

9/10 Wonderful! (791 reviews)

Second mother / daughter trip to Key West - first time staying at Lighthouse Hotel. We loved it! The hotel is charming and the location is perfect. The staff was super friendly and answered all of our questions. Pool area and bar is great and we enjoyed a nice breakfast every morning before venturing out for the day. We rented bikes to get around and this location was ideal - easy ride to everywhere we wanted to go. We had a great stay and will definitely book this hotel again!

Reviewed on Sep 22, 2025

Hyatt Vacation Club at Windward Pointe, Key West

Save 100% on your flight

$667

per person

Nov 10 - Nov 14

found 1 day ago

Roundtrip non-stop flight included

Boston (BOS) to Key West (EYW)

9.6/10 Exceptional! (1,016 reviews)

This property was accommodating, staff friendly, courteous, clean, and concierge was extremely helpful. Will visit again soon.

Reviewed on Sep 26, 2025

The Key West Hotel

Key West Historic District

Save 100% on your flight

$639

per person

Dec 12 - Dec 15

found 1 day ago

Roundtrip non-stop flight included

Boston (BOS) to Key West (EYW)

9.2/10 Wonderful! (496 reviews)

Excellent location right in the heart of town super friendly staff and very nice property

Reviewed on Aug 3, 2025

Winslow's Bungalows - Key West Historic Inns

Old Town Key West

Save 100% on your flight

$768

per person

Nov 10 - Nov 14

found 1 day ago

Roundtrip non-stop flight included

Boston (BOS) to Key West (EYW)

9.2/10 Wonderful! (1,005 reviews)

Everyone and everything was great, such a great location to enjoy the whole island!

Reviewed on Sep 28, 2025

Don't see what you're looking for?

See all available trips from Columbus to Rockland Key

View all trips

Rockland Key Hotel Deals

Margaritaville Beach House Key West

2001 South Roosevelt Boulevard, Key West, FL

Fully refundableReserve now, pay when you stay

$235 nightly

$264 total

Oct 14 - Oct 15

Total with taxes and fees

8.6/10 Excellent! (1,790 reviews)

"We went during off peak season and it was amazing and quiet, relaxing."

Reviewed on Sep 23, 2025

Oceans Edge Key West Resort, Hotel & Marina

5950 Peninsular Avenue, Key West, FL

Fully refundableReserve now, pay when you stay

$199 nightly

$223 total

Oct 13 - Oct 14

Total with taxes and fees

8.8/10 Excellent! (1,738 reviews)

"Very good for visiting"

Reviewed on Sep 27, 2025

Southernmost Beach Resort and Guesthouses

1319 Duval Street, Key West, FL

Fully refundable

$229 nightly

$258 total

Oct 29 - Oct 30

Total with taxes and fees

8.6/10 Excellent! (2,788 reviews)

"Great"

Reviewed on Sep 28, 2025

See all 3,359 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.