Name: Southernmost Beach Resort and Guesthouses
Price range: $294 total
Rating: 8.8

Plan, book, travel with confidence
Better together
Save up to $2,000 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.

The Perry Hotel & Marina Key West

Save 100% on your flight

$398

per person

Aug 1 - Aug 5

found 1 day ago

Roundtrip flight included

Atlanta (ATL) to Key West (EYW)

9.4/10 Exceptional! (1,277 reviews)

Clean, comfortable, friendly, helpful staff. Pool area is convenient and well maintained. Love the shuttle service to and from town

Reviewed on May 20, 2026

Hyatt Vacation Club at Windward Pointe, Key West

Save 100% on your flight

$807

per person

Aug 1 - Aug 5

found 1 day ago

Roundtrip flight included

Atlanta (ATL) to Key West (EYW)

9.4/10 Exceptional! (1,089 reviews)

Amazing resort to stay at. All the amenities they offer made it wonderful. Very clean and quiet and not to far of a drive to the other side of island

Reviewed on May 21, 2026

Hyatt Vacation Club at Sunset Harbor, Key West

Old Town Key West

Save 100% on your flight

$932

per person

Aug 1 - Aug 5

found 1 day ago

Roundtrip flight included

Atlanta (ATL) to Key West (EYW)

8.6/10 Excellent! (371 reviews)

Wished we had paid more for a unit that at least had a window other than to a hallway. Room was clean but not spotless. Found at least 3 long hairs in the bathroom area. Staff at desk was quite abrupt and condescending. At check in AND check out. Gave 4 stars but 5 stars could easily be reached with just a little more attention to detail

Reviewed on May 18, 2026

Oceans Edge Key West Resort, Hotel & Marina

Save 100% on your flight

$453

per person

Aug 1 - Aug 5

found 1 day ago

Roundtrip flight included

Atlanta (ATL) to Key West (EYW)

9/10 Wonderful! (1,862 reviews)

Beautiful property will definitely be back again

Reviewed on May 21, 2026

The Key West Hotel

Key West Historic District

Save 100% on your flight

$1,285

per person

Aug 14 - Aug 18

found 1 day ago

Roundtrip flight included

Atlanta (ATL) to Key West (EYW)

9.2/10 Wonderful! (552 reviews)

Our room was spacious and clean, with a bag of Key Lime cookies waiting for us on arrival. We appreciated boxed instead of bottled water that was always available in-room at no extra cost. But the thing we enjoyed most was the secluded Bali Bar, which was hidden away from busy Duvall Street. The live music was excellent and the. bar tenders were very accommodating. There are many hotels and places to stay in Key West but we would definitely return to this one. Highly recommend!

Reviewed on May 18, 2026

Don't see what you're looking for?

See all available trips from Columbus to Rockland Key

View all trips

Rockland Key Hotel Deals

Blue Flamingo Resort Key West

3820 North Roosevelt Boulevard Key West FL

Fully refundableReserve now, pay when you stay

$190 nightly

$214 total

May 27 - May 28

Total with taxes and fees

8.4/10 Very Good! (2,256 reviews)

"Clean and comfortable place to stay pools clean and plenty of chairs there was on site bar/restaurant near our floor/pool area but did not utilize it the pool was used snd very nice both of them we went to the second pool when the teens came out im the evening to play football passing game they did ..."

Reviewed on May 21, 2026

Margaritaville Beach House Key West

2001 South Roosevelt Boulevard Key West FL

Fully refundableReserve now, pay when you stay

$281 nightly

$316 total

May 31 - Jun 1

Total with taxes and fees

8.8/10 Excellent! (1,796 reviews)

"Very happy with the service very nice people to deal with"

Reviewed on May 21, 2026

Southernmost Beach Resort and Guesthouses

1319 Duval Street Key West FL

Fully refundable

$261 nightly

$294 total

Jun 8 - Jun 9

Total with taxes and fees

8.8/10 Excellent! (3,347 reviews)

"Upon check in - I was informed I needed a CC with $1200.00 available on it - at no point was I instructed of this need - I had paid for my stay prior as I do not use CC - thank goodness some in my party had one to use. The front desk person was not friendly about this = I have read my information ..."

Reviewed on May 21, 2026

See all 3,308 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.