Sunset Key Vacation Packages
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Top Sunset Key vacation package deals
Price found within the past 48 hours. Click for updated prices.
3.5-star property
Hyatt Vacation Club at Windward Pointe, Key West
9.4/10 Exceptional! (1,020 reviews)
Jun 19 - Jun 22
3 night stay
Boston (BOS) to Key West (EYW)
American Airlines • Non-stop roundtrip • Coach
Price was $1,472, price is now $1,012 per person
$1,012
per person
found 1 day ago
Staff was fantastic, room and grounds very clean and well kept.
Reviewed on Feb 12, 2026
2.5-star property
The Key West Hotel
Key West Historic District
9.2/10 Wonderful! (536 reviews)
Jun 11 - Jun 14
3 night stay
Boston (BOS) to Key West (EYW)
United • Non-stop • Coach
Key West (EYW) to Boston (BOS)
American Airlines • Non-stop • Coach
Price was $2,163, price is now $1,442 per person
$1,442
per person
found 1 day ago
Gorgeous property right on Duval Street but hidden from the noise and bustle. Convenient to everything you want to do and see. Wonderfully helpful and friendly staff.
Reviewed on Jan 5, 2025
4.0-star property
Winslow's Bungalows - Key West Historic Inns
Old Town Key West
9.2/10 Wonderful! (1,194 reviews)
Apr 29 - May 4
5 night stay
Boston (BOS) to Key West (EYW)
Delta • Non-stop • Coach
Key West (EYW) to Boston (BOS)
Spirit Airlines • Non-stop • Coach
Save 100% on your flight
Price was $2,284, price is now $1,597 per person
$1,597
per person
found 1 day ago
The room was clean and location was great
Reviewed on Feb 22, 2026
4.0-star property
The Reach Key West, Curio Collection by Hilton
Old Town Key West
8.6/10 Excellent! (1,013 reviews)
Apr 29 - May 4
5 night stay
Boston (BOS) to Key West (EYW)
Delta • Non-stop • Coach
Key West (EYW) to Boston (BOS)
Spirit Airlines • Non-stop • Coach
Save 100% on your flight
Price was $2,624, price is now $1,862 per person
$1,862
per person
found 1 day ago
Beautiful beach, great restaurant
Reviewed on Jan 22, 2026
3.0-star property
Brisa Del Mar by Avantstay Communal Pool Gated Community Ocean Front
9/10 Wonderful! (2 reviews)
Jun 4 - Jun 9
5 night stay
Boston (BOS) to Key West (EYW)
American Airlines • Roundtrip • Coach
Save 100% on your flight
Price was $2,507, price is now $1,782 per person
$1,782
per person
found 11 hours ago
Top rated hotels for your Sunset Key vacation package
Blue Flamingo Resort Key West
3820 North Roosevelt Boulevard Key West FL
Free Cancellation
Reserve now, pay when you stay
3.75 mi from Sunset Key
$310 nightly
The price is $349 total per night
$349 total
Apr 19 - Apr 20
Total with taxes and fees
Blue Flamingo Resort Key West features 2 outdoor pools, karaoke, and a 24-hour gym. If you drive, self parking is USD 15.00 per night, and there's also a free area shuttle. The 24-hour front desk has multilingual staff ready to assist with concierge services and luggage storage. If you like to take your furry friend along on your adventures, this pet-friendly property offers an off-leash area. Other amenities at this family-friendly hotel include free WiFi in public areas, a hot tub, and meeting rooms.
Pool
Hot Tub
Margaritaville Beach House Key West
2001 South Roosevelt Boulevard Key West FL
Free Cancellation
Reserve now, pay when you stay
2.68 mi from Sunset Key
$377 nightly
The price is $424 total per night
$424 total
Apr 28 - Apr 29
Total with taxes and fees
Margaritaville Beach House Key West features an outdoor pool, a 24-hour gym, and a business center. The front desk is staffed 24/7 to help with tours or tickets, luggage storage, and dry cleaning/laundry. If you like to take your furry friend along on your adventures, this pet-friendly property offers food and water bowls. Other amenities at this beach hotel include a banquet hall and an ATM.
Pool
Pet friendly
Beachside Resort & Residences
3841 N Roosevelt Blvd Key West FL
Free Cancellation
Reserve now, pay when you stay
3.88 mi from Sunset Key
$325 nightly
The price is $366 total per night
$366 total
Mar 31 - Apr 1
Total with taxes and fees
Guests of Beachside Resort & Residences have access to a private beach, a marina, and an outdoor pool. If you drive, self parking is USD 25.00 per night, and there's also a free area shuttle. The front desk has multilingual staff on hand 24/7 to help with luggage storage, dry cleaning/laundry, and concierge services. Other amenities at this beach hotel include a 24-hour gym, free WiFi in public areas, and a hot tub.
On private beach
Pool
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.