Rockland Key Vacations from $1,047

Name: Beachside Resort & Residences
Price range: $414 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.

Hyatt Vacation Club at Windward Pointe, Key West

$1,047

per person

Jun 12 - Jun 15

found 1 day ago

Roundtrip non-stop flight included

Boston (BOS) to Key West (EYW)

9.4/10 Exceptional! (1,020 reviews)

The shops are not very near. Pool is very good. The restaurant inside is also very good.

Reviewed on Mar 23, 2026

The Key West Hotel

Key West Historic District

Save 100% on your flight

$1,200

per person

May 24 - May 27

found 1 day ago

Roundtrip non-stop flight included

Boston (BOS) to Key West (EYW)

9.2/10 Wonderful! (536 reviews)

Love this place! Perfect location, nice rooms and cool bar with live music every night on site!

Reviewed on Mar 17, 2026

Brisa Del Mar by Avantstay Communal Pool Gated Community Ocean Front

Save 100% on your flight

$2,068

per person

May 6 - May 13

found 1 day ago

Roundtrip non-stop flight included

Boston (BOS) to Key West (EYW)

9/10 Wonderful! (2 reviews)

Hyatt Vacation Club at Beach House, Key West

$1,287

per person

May 27 - May 31

found 4 hours ago

Roundtrip non-stop flight included

Boston (BOS) to Key West (EYW)

9.4/10 Exceptional! (1,019 reviews)

Everything about this property was amazing from the staff, to the clean rooms, to the pool!

Reviewed on Mar 23, 2026

Duval Breeze by Avantstay Great Location Close to Beach & Nightlife Shared Pool! Week Long Stays

Old Town Key West

Save 100% on your flight

$2,354

per person

Jun 14 - Jun 20

found 15 hours ago

Roundtrip flight included

Newark Liberty Intl. Airport (EWR) to Key West (EYW)

No reviews

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Rockland Key Hotel Deals

Margaritaville Beach House Key West

2001 South Roosevelt Boulevard Key West FL

Fully refundableReserve now, pay when you stay

$351 nightly

$395 total

Apr 20 - Apr 21

Total with taxes and fees

8.8/10 Excellent! (1,797 reviews)

Overall nice poolside room. However, hallways show how run down the place is getting. It’s like they put lipstick on a pig. Inside aka room were great. No issues. Staff very pleasant.

Reviewed on Mar 24, 2026

Blue Flamingo Resort Key West

3820 North Roosevelt Boulevard Key West FL

Fully refundableReserve now, pay when you stay

$310 nightly

$349 total

Apr 19 - Apr 20

Total with taxes and fees

8.2/10 Very Good! (1,999 reviews)

Our stay was fine, although value for the rate we paid was not good. We paid for an upgrade (although I am Expedia Platinium) to a supposedly better room which was very noisy. The staff was nice about it when I complained in the morning and gave us a discount.

Reviewed on Mar 23, 2026

Beachside Resort & Residences

3841 N Roosevelt Blvd Key West FL

Fully refundableReserve now, pay when you stay

$368 nightly

$414 total

Apr 13 - Apr 14

Total with taxes and fees

8.6/10 Excellent! (2,089 reviews)

Shuttle times are extremely accurate. Beautfil place with friendly staff. Only wish checkout time was a bit later. Elevators were out our entire stay. We were on third floor. The staff did offer to help carry our luggage up.

Reviewed on Mar 22, 2026

See all 3,314 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.