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
Lighthouse Hotel - Key West Historic Inns
Old Town Key West
9/10 Wonderful! (981 reviews)
Nov 18 - Nov 22
4 night stay
Hartford (BDL) to Key West (EYW)
American Airlines • Non-stop roundtrip • Coach
Price was $1,309, price is now $894 per person
$894
per person
found 1 day ago
Great stay 2nd year in a row! This time I enjoyed the bar and specialty drinks! Staff excellent as well!
Reviewed on Aug 28, 2026
3.0-star property
The Key West Hotel
Key West Historic District
9.2/10 Wonderful! (562 reviews)
Nov 4 - Nov 9
5 night stay
Hartford (BDL) to Key West (EYW)
American Airlines • Non-stop roundtrip • Coach
Save 100% on your flight
Price was $5,434, price is now $3,289 per person
$3,289
per person
found 1 day ago
Great place to stay - highly recommend.
Reviewed on Aug 20, 2026
4.0-star property
Winslow's Bungalows - Key West Historic Inns
Old Town Key West
9.2/10 Wonderful! (1,389 reviews)
Nov 18 - Nov 22
4 night stay
Hartford (BDL) to Key West (EYW)
American Airlines • Non-stop roundtrip • Coach
Save 100% on your flight
Price was $1,483, price is now $958 per person
$958
per person
found 1 day ago
Great property and staff
Reviewed on Aug 27, 2026
3.5-star property
Ridley House - Key West Historic Inns
Key West Historic District
9.2/10 Wonderful! (951 reviews)
Oct 5 - Oct 11
6 night stay
Hartford (BDL) to Key West (EYW)
Breeze Airways • Non-stop roundtrip • Coach
Save 100% on your flight
Price was $1,636, price is now $1,075 per person
$1,075
per person
found 1 day ago
Top rated hotels for your Sunset Key vacation package
Southernmost Beach Resort and Guesthouses
1319 Duval Street Key West FL
Free Cancellation
Reserve now, pay when you stay
1.44 mi from Sunset Key
$210 nightly
The price is $237 total per night
$237 total
Sep 8 - Sep 9
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 dry cleaning/laundry, concierge services, and luggage storage. Other amenities at this spa hotel include conference space, coffee/tea in a common area, and a computer station.
Ibis Bay Beach Resort
3101 N. Roosevelt Blvd Key West FL
Free Cancellation
Reserve now, pay when you stay
2.83 mi from Sunset Key
$136 nightly
The price is $153 total per night
$153 total
Aug 30 - Aug 31
Total with taxes and fees
Guests of Ibis Bay Beach Resort have access to a private beach, a marina, and an outdoor pool. The front desk has multilingual staff that can help with tours/tickets and luggage storage. Other amenities at this beach hotel include free WiFi in public areas, coffee/tea in a common area, and a computer station.
On private beach
Pool
Havana Cabana at Key West
3420 N. Roosevelt Blvd Key West FL
Free Cancellation
Reserve now, pay when you stay
3.31 mi from Sunset Key
$195 nightly
The price is $220 total per night
$220 total
Aug 31 - Sep 1
Total with taxes and fees
At Havana Cabana at Key West , guests have access to an outdoor pool, free WiFi in public areas, and a hot tub. A stay here includes free parking. The 24-hour front desk has multilingual staff ready to assist 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. Additional amenities include a meeting room, a terrace, and a garden.
Pool
Hot Tub
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.
Things to do
Key West Morning Snorkel Adventure with Bottomless Mimosas & Breakfast
$45
per adult
94% of travellers recommend
Key West Coral Reef Snorkel with Mimosas, Margaritas or Rum Punch
$61
per adult
86% of travellers recommend
Dolphin Watch Catamaran Sunset Sail w/ Tapas and Open Bar
$79
per adult
94% of travellers recommend