Name: Beachside Resort & Residences
Price range: $217 total
Rating: 8.6

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The Latest Rockland Key vacation packages

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

Winslow's Bungalows - Key West Historic Inns

Old Town Key West

Save 100% on your flight

$492

per person

Jan 14 - Jan 16

found 1 day ago

Roundtrip flight included

Boston (BOS) to Key West (EYW)

9.2/10 Wonderful! (1,021 reviews)

Room was v clean, staff super friendly, continental breakfast was ok. The balcony was a communal balcony so we did not use it

Reviewed on Nov 3, 2025

Hyatt Vacation Club at Beach House, Key West

Save 100% on your flight

$821

per person

Dec 23 - Dec 26

found 1 day ago

Roundtrip flight included

Boston (BOS) to Key West (EYW)

9.4/10 Exceptional! (1,010 reviews)

Rooms was spotless

Reviewed on Nov 5, 2025

Ella's Cottages - Key West Historic Inns

Old Town Key West

Save 100% on your flight

$871

per person

Jan 14 - Jan 16

found 1 day ago

Roundtrip flight included

Boston (BOS) to Key West (EYW)

9.4/10 Exceptional! (378 reviews)

Walking distance to main street

Reviewed on Nov 2, 2025

The Key West Hotel

Key West Historic District

Save 100% on your flight

$2,324

per person

Jan 22 - Jan 26

found 1 day ago

Roundtrip flight included

Boston (BOS) to Key West (EYW)

9.2/10 Wonderful! (498 reviews)

Great location and friendly staff. They have remodeled a lot and are doing a super job. Nice decorations and LOVE the tiki bar and pool area. Key West Aloe products were a nice touch as well as the key lime cookies. The porch deck and handrail outside the Envy/Lust room needs a little attention. Overall, very comfortable and accommodating. I would definitely stay here again.

Reviewed on Oct 17, 2025

Hyatt Vacation Club at Windward Pointe, Key West

Save 100% on your flight

$780

per person

Jan 3 - Jan 6

found 1 day ago

Roundtrip flight included

Boston (BOS) to Key West (EYW)

9.6/10 Exceptional! (1,016 reviews)

Great experience all around would recommend 100%

Reviewed on Nov 6, 2025

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Rockland Key Hotel Deals

Oceans Edge Key West Resort, Hotel & Marina

5950 Peninsular Avenue, Key West, FL

Fully refundableReserve now, pay when you stay

$206 nightly

$232 total

Nov 16 - Nov 17

Total with taxes and fees

8.8/10 Excellent! (1,733 reviews)

We’ve stayed here twice now. Staff is great, the shuttle into town is super convenient (hi Jeffrey!). We love that you can use the kayaks or paddleboards every day. The tiki hut crew is the best! The place is clean and I feel safe walking around there. It’s well lit and easy to navigate.

Reviewed on Nov 2, 2025

Blue Flamingo Resort Key West

3820 North Roosevelt Boulevard, Key West, FL

Fully refundableReserve now, pay when you stay

$157 nightly

$177 total

Nov 18 - Nov 19

Total with taxes and fees

7.8/10 Good! (1,648 reviews)

Beautiful room, great view, love the pools, bars and lawn games

Reviewed on Nov 3, 2025

Beachside Resort & Residences

3841 N Roosevelt Blvd, Key West, FL

Fully refundableReserve now, pay when you stay

$193 nightly

$217 total

Nov 17 - Nov 18

Total with taxes and fees

8.6/10 Excellent! (1,655 reviews)

Staff good but never clean our room

Reviewed on Nov 3, 2025

See all 3,370 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.