
Sunset Key Vacation Packages
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Top Sunset Key vacation package deals
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3.5-star property
Hyatt Vacation Club at Windward Pointe, Key West
9.6/10 Exceptional! (1,002 reviews)
Feb 19 - Feb 24
5 night stay
Boston (BOS) to Key West (EYW)
Spirit Airlines • Roundtrip • Coach
Price was $1,633, price is now $875 per person
$875
per person
found 1 day ago
Pool and service was great!!! Staff always pleasant and helpful!
Reviewed on Dec 6, 2025

3.5-star property
Hyatt Vacation Club at Beach House, Key West
9.4/10 Exceptional! (1,002 reviews)
Mar 12 - Mar 19
7 night stay
Boston (BOS) to Key West (EYW)
American Airlines • Non-stop roundtrip • Coach
Save 100% on your flight
Price was $2,351, price is now $1,388 per person
$1,388
per person
found 1 day ago
The property was truly amazing. We.rented a 2 bedroom villa and it was comfortable and very well decorated and equipped. The only complaint would be the " complimentary breakfast" needs to be better. It was only a selection of cruisants with water and orange juice. For the price spent, please add eggs, meat and coffee at least. Other than that, it was very nice
Reviewed on Sep 7, 2025

3.5-star property
Ella's Cottages - Key West Historic Inns
Old Town Key West
9.4/10 Exceptional! (390 reviews)
Mar 12 - Mar 19
7 night stay
Boston (BOS) to Key West (EYW)
American Airlines • Non-stop roundtrip • Coach
Save 100% on your flight
Price was $4,103, price is now $2,470 per person
$2,470
per person
found 1 day ago
We chose this historic inn based on central location to everything we wanted in less than 15 min. Front desk staff (Dwight and others) are fantastic and always willing to listen and provide assistance. Fort Zachary Taylor Beach Park is walkable - 25 min (beach water shoes recommended due to rocks). We didn't need to rent any transportation as it was easier for us to walk it out, so I can't comment on parking since I didn't use it (it is limited at most places). We felt very safe walking around, even at night. We used a taxi to and from Key West airport (both drivers familiar with this inn). Room is clean. Both night stands have power and USB charging outlets. Excellent daily room service and Sunshine Breakfast basket hand delivered to your room. Duval Loop bus stop 14 (free) in front of inn (bus route loop is an hour long and two buses running to ensure next bus in 30 min), so this is another convenient option if walking isn't your thing.
Reviewed on Dec 17, 2024

4.0-star property
Winslow's Bungalows - Key West Historic Inns
Old Town Key West
9.2/10 Wonderful! (1,075 reviews)
Mar 12 - Mar 19
7 night stay
Boston (BOS) to Key West (EYW)
American Airlines • Non-stop roundtrip • Coach
Save 100% on your flight
Price was $2,967, price is now $1,830 per person
$1,830
per person
found 1 day ago
Professional staff, lovely rooms
Reviewed on Oct 21, 2025

2.5-star property
The Key West Hotel
Key West Historic District
9.2/10 Wonderful! (505 reviews)
Mar 2 - Mar 9
7 night stay
Boston (BOS) to Key West (EYW)
Delta • Non-stop • FirstClass
Key West (EYW) to Boston (BOS)
American Airlines • Non-stop • FirstClass
Price was $5,663, price is now $3,494 per person
$3,494
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
Top rated hotels for your Sunset Key vacation package

Beachside Resort & Residences
3841 N Roosevelt Blvd Key West FL
Free Cancellation
Reserve now, pay when you stay
3.88 mi from Sunset Key
$289 nightly
The price is $325 total per night
$325 total
Dec 21 - Dec 22
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 dry cleaning/laundry, concierge services, and luggage storage. Other amenities at this beach hotel include a 24-hour gym, free WiFi in public areas, and a hot tub.
On private beach
Pool

Blue Flamingo Resort Key West
3820 North Roosevelt Boulevard Key West FL
Free Cancellation
Reserve now, pay when you stay
3.74 mi from Sunset Key
$283 nightly
The price is $318 total per night
$318 total
Dec 21 - Dec 22
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 luggage storage and concierge services. 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

Southernmost Beach Resort and Guesthouses
1319 Duval Street Key West FL
Free Cancellation
1.46 mi from Sunset Key
$345 nightly
The price is $389 total per night
$389 total
Jan 13 - Jan 14, 2026
Total with taxes and fees
Guests of Southernmost Beach Resort and Guesthouses have access to a full-service spa, 3 outdoor pools, and a gym. Self parking is offered for USD 53.75 per day. Multilingual staff at the 24-hour front desk can assist with concierge services, dry cleaning/laundry, and luggage storage. Other amenities at this beach hotel include conference space, a 24-hour business center, and coffee/tea in a common area.
Pool
Spa
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.