
Sunset Key Vacation Packages
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Price found within the past 48 hours. Click for updated prices.

4.0-star property
Oceans Edge Key West Resort, Hotel & Marina
9/10 Wonderful! (1,825 reviews)
Jun 13 - Jun 20
7 night stay
Boston (BOS) to Key West (EYW)
United • Non-stop • Coach
Key West (EYW) to Boston (BOS)
Delta • Non-stop • Coach
Price was $2,119, price is now $1,427 per person
$1,427
per person
found 1 day ago
We LOVED the setting and the surrounding area! Absolutely beautiful!
Be aware the hotel IS in the airport landing zone. If you like to watch/hear commercial planes you'll be very happy.
Ask for a room on the top floor only - so you can (1) look over the marina AND (2) so you won't hear people moving chairs on their balcony above you.
The max/min air conditioning is centrally controlled. If you want it colder than 67, you will not be able to. Not sure what the max heat was.
Be extra vigilant about putting a thick towel on the floor to soak up any water that gets past the shower door. It WILL happen! Please do not slip on the wet tile floor!
Be aware that if you want/need a later checkout, they will charge you an additional $50/hour past their usual checkout time of 11am.
Be prepared for onsite meal expenses. They are very good, but they ARE on the pricy side.
Our particular room smelled strongly of smoke on arrival. I'm nearly POSITIVE we asked for a nonsmoking room as we both have underlying medical problems that preclude exposre to smoke. Perhaps call ahead to ENSURE you get a nonsmoking on arrival. The entire hotel was booked so we did not have any other choice.
Reviewed on Dec 28, 2025

2.5-star property
The Key West Hotel
Key West Historic District
9.2/10 Wonderful! (536 reviews)
May 19 - May 26
7 night stay
Boston (BOS) to Key West (EYW)
Delta • Non-stop roundtrip • Coach
Save 100% on your flight
Price was $3,431, price is now $2,073 per person
$2,073
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

3.5-star property
Hyatt Vacation Club at Windward Pointe, Key West
9.4/10 Exceptional! (1,020 reviews)
May 19 - May 26
7 night stay
Boston (BOS) to Key West (EYW)
Delta • Non-stop roundtrip • Coach
Save 100% on your flight
Price was $2,873, price is now $1,812 per person
$1,812
per person
found 1 day ago
Staff was fantastic, room and grounds very clean and well kept.
Reviewed on Feb 12, 2026

3.5-star property
Hyatt Vacation Club at Beach House, Key West
9.4/10 Exceptional! (1,019 reviews)
Jun 13 - Jun 20
7 night stay
Boston (BOS) to Key West (EYW)
United • Non-stop • Coach
Key West (EYW) to Boston (BOS)
Delta • Non-stop • Coach
Price was $2,834, price is now $1,926 per person
$1,926
per person
found 1 day ago
The staff here were phenomenal! They were all so welcoming and kind. Made for a great experience!
Reviewed on Jan 21, 2026

4.0-star property
Winslow's Bungalows - Key West Historic Inns
Old Town Key West
9.2/10 Wonderful! (1,194 reviews)
May 1 - May 8
7 night stay
Boston (BOS) to Key West (EYW)
American Airlines • Non-stop roundtrip • Coach
Save 100% on your flight
Price was $2,373, price is now $1,637 per person
$1,637
per person
found 1 day ago
The room was clean and location was great
Reviewed on Feb 22, 2026
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
$309 nightly
The price is $348 total per night
$348 total
Mar 30 - Mar 31
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.