Key West Adventure Vacation Packages
Best Key West Adventure packages
Price found within the past 48 hours. Click for updated prices.
Southernmost Beach Resort and Guesthouses
Old Town Key West
Price was $954, price is now $784 per person
$784
per person
Nov 28 - Dec 1
found 24 hours ago
Roundtrip flight included
Chicago (CHI) to Key West (EYW)
Book a stay at this spa hotel in Key West. Enjoy 3 outdoor pools, a full-service spa, and 2 poolside bars. Our guests praise the pool and the helpful staff in our reviews. Popular attractions Duval Street and Southernmost Point are located nearby.
The room was perfectly clean and comfortable. However, our experience with the staff was a bit mixed. While some of the bartenders were incredibly friendly and welcoming, a few others could definitely use some training in hospitality and politeness. Additionally, it would be great if breakfast hours could be extended a bit later. When people are on vacation, they want to sleep in without worrying about missing the morning meal!
Reviewed on Oct 25, 2026
Duval House
Old Town Key West
Price was $1,289, price is now $1,029 per person
$1,029
per person
Nov 1 - Nov 4
found 1 day ago
Roundtrip non-stop flight included
Buffalo (BUF) to Key West (EYW)
Stay at this B&B in Key West. Enjoy parking (surcharge), daily housekeeping, and a garden. Our guests praise the breakfast and the pool in our reviews. Popular attractions Duval Street and Ernest Hemingway Home and Museum are located nearby.
The Marker Key West Harbor Resort
Key West Historic District
Price was $1,079, price is now $872 per person
$872
per person
Nov 28 - Dec 1
found 24 hours ago
Roundtrip flight included
Chicago (CHI) to Key West (EYW)
Book a stay at this business-friendly hotel in Key West. Enjoy free WiFi, 3 outdoor pools, and breakfast (surcharge). Our guests praise the pool and the helpful staff in our reviews. Popular attractions Duval Street and Mallory Square are located nearby.
Love this place!!!
Reviewed on Oct 24, 2026
3 night Key West Adventure vacation packages with airfare
Price found within the past 48 hours. Click for updated prices.
Courtyard by Marriott Key West Waterfront
Northside Resort
Price was $1,276, price is now $969 per person
$969
per person
Nov 29 - Dec 2
found 10 hours ago
Roundtrip non-stop flight included
Detroit (DTW) to Key West (EYW)
Book a stay at this beach hotel in Key West. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the pool and the helpful staff in our reviews. Popular attractions Duval Street and Smathers Beach are located nearby.
The property was comfortable and inviting. The pool is incredibly beautiful and quiet. Everyone was very helpful and courteous.
Reviewed on Oct 22, 2026
The Marker Key West Harbor Resort
Key West Historic District
Price was $3,181, price is now $2,457 per person
$2,457
per person
Dec 29 - Jan 1
found 1 day ago
Roundtrip non-stop flight included
Detroit (DTW) to Key West (EYW)
Book a stay at this business-friendly hotel in Key West. Enjoy free WiFi, 3 outdoor pools, and breakfast (surcharge). Our guests praise the pool and the helpful staff in our reviews. Popular attractions Duval Street and Mallory Square are located nearby.
Love this place!!!
Reviewed on Oct 24, 2026
Southernmost Beach Resort and Guesthouses
Old Town Key West
Price was $2,909, price is now $2,275 per person
$2,275
per person
Dec 29 - Jan 1
found 1 day ago
Roundtrip non-stop flight included
Detroit (DTW) to Key West (EYW)
Book a stay at this spa hotel in Key West. Enjoy 3 outdoor pools, a full-service spa, and 2 poolside bars. Our guests praise the pool and the helpful staff in our reviews. Popular attractions Duval Street and Southernmost Point are located nearby.
The room was perfectly clean and comfortable. However, our experience with the staff was a bit mixed. While some of the bartenders were incredibly friendly and welcoming, a few others could definitely use some training in hospitality and politeness. Additionally, it would be great if breakfast hours could be extended a bit later. When people are on vacation, they want to sleep in without worrying about missing the morning meal!
Reviewed on Oct 25, 2026
4 night Key West Adventure vacation packages with flight
Price found within the past 48 hours. Click for updated prices.
Southernmost House - Adult Exclusive
Old Town Key West
Save 100% on your flight
Price was $2,194, price is now $1,442 per person
$1,442
per person
Oct 30 - Nov 3
found 1 day ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Key West (EYW)
Book a stay at this beach hotel in Key West. Enjoy free breakfast, free WiFi, and parking (surcharge). Our guests praise the helpful staff and the property condition in our reviews. Popular attractions Duval Street and South Beach are located nearby.
staff was super friendly and accomodating
Reviewed on Oct 22, 2026
The Gardens Hotel
Old Town Key West
Save 100% on your flight
Price was $3,002, price is now $2,313 per person
$2,313
per person
Jan 1 - Jan 5
found 1 day ago
Roundtrip non-stop flight included
Columbus (CMH) to Key West (EYW)
Book a stay at this business-friendly B&B in Key West. Enjoy free breakfast, free WiFi, and 2 outdoor pools. Our guests praise the pool and the helpful staff in our reviews. Popular attractions Duval Street and Ernest Hemingway Home and Museum are located nearby.
Un hotel hermoso , limpio , con una localización insuperable . El servio de primera , volveré pronto
Reviewed on Oct 20, 2026
The Marker Key West Harbor Resort
Key West Historic District
Price was $4,330, price is now $3,394 per person
$3,394
per person
Dec 29 - Jan 2
found 1 day ago
Roundtrip non-stop flight included
Austin (AUS) to Key West (EYW)
Book a stay at this business-friendly hotel in Key West. Enjoy free WiFi, 3 outdoor pools, and breakfast (surcharge). Our guests praise the pool and the helpful staff in our reviews. Popular attractions Duval Street and Mallory Square are located nearby.
Love this place!!!
Reviewed on Oct 24, 2026
5 night Key West Adventure vacation packages with airfare included
Price found within the past 48 hours. Click for updated prices.
Orchid Key Inn - Adults Only
Old Town Key West
Save 100% on your flight
Price was $1,384, price is now $996 per person
$996
per person
Nov 28 - Dec 3
found 15 hours ago
Roundtrip flight included
New York (NYC) to Key West (EYW)
Stay at this hotel in Key West. Enjoy free breakfast, parking (surcharge), and a 24-hour front desk. Our guests praise the breakfast and the pool in our reviews. Popular attractions Duval Street and Ernest Hemingway Home and Museum are located nearby.
The Marker Key West Harbor Resort
Key West Historic District
Save 100% on your flight
Price was $4,024, price is now $2,927 per person
$2,927
per person
Dec 29 - Jan 3
found 11 hours ago
Roundtrip non-stop flight included
Wilkes-Barre (AVP) to Key West (EYW)
Book a stay at this business-friendly hotel in Key West. Enjoy free WiFi, 3 outdoor pools, and breakfast (surcharge). Our guests praise the pool and the helpful staff in our reviews. Popular attractions Duval Street and Mallory Square are located nearby.
Love this place!!!
Reviewed on Oct 24, 2026
Southernmost Beach Resort and Guesthouses
Old Town Key West
Save 100% on your flight
Price was $3,678, price is now $2,703 per person
$2,703
per person
Dec 29 - Jan 3
found 11 hours ago
Roundtrip non-stop flight included
Wilkes-Barre (AVP) to Key West (EYW)
Book a stay at this spa hotel in Key West. Enjoy 3 outdoor pools, a full-service spa, and 2 poolside bars. Our guests praise the pool and the helpful staff in our reviews. Popular attractions Duval Street and Southernmost Point are located nearby.
The room was perfectly clean and comfortable. However, our experience with the staff was a bit mixed. While some of the bartenders were incredibly friendly and welcoming, a few others could definitely use some training in hospitality and politeness. Additionally, it would be great if breakfast hours could be extended a bit later. When people are on vacation, they want to sleep in without worrying about missing the morning meal!
Reviewed on Oct 25, 2026
Adventure vacation packages for 6-7 nights
Price found within the past 48 hours. Click for updated prices.
Eden House
Key West Historic District
Save 100% on your flight
Price was $2,373, price is now $1,832 per person
$1,832
per person
Nov 28 - Dec 5
found 1 day ago
Roundtrip non-stop flight included
Greenville (GSP) to Key West (EYW)
Stay at this hotel in Key West. Enjoy free WiFi, in-room massages, and a 24-hour front desk. Our guests praise the pool and the helpful staff in our reviews. Popular attractions Duval Street and Ernest Hemingway Home and Museum are located nearby.
Great place. It has quiet space and fun laid music space. Room options make it great basic to full kitchen private bedroom and a porch with a swing and rocking chair.
Reviewed on Oct 24, 2026
The Marker Key West Harbor Resort
Key West Historic District
Save 100% on your flight
Price was $4,722, price is now $3,382 per person
$3,382
per person
Dec 29 - Jan 5
found 14 hours ago
Roundtrip non-stop flight included
Detroit (DTW) to Key West (EYW)
Book a stay at this business-friendly hotel in Key West. Enjoy free WiFi, 3 outdoor pools, and breakfast (surcharge). Our guests praise the pool and the helpful staff in our reviews. Popular attractions Duval Street and Mallory Square are located nearby.
Love this place!!!
Reviewed on Oct 24, 2026
Southernmost Beach Resort and Guesthouses
Old Town Key West
Save 100% on your flight
Price was $4,016, price is now $2,945 per person
$2,945
per person
Dec 29 - Jan 4
found 1 day ago
Roundtrip flight included
Boston (BOS) to Key West (EYW)
Book a stay at this spa hotel in Key West. Enjoy 3 outdoor pools, a full-service spa, and 2 poolside bars. Our guests praise the pool and the helpful staff in our reviews. Popular attractions Duval Street and Southernmost Point are located nearby.
The room was perfectly clean and comfortable. However, our experience with the staff was a bit mixed. While some of the bartenders were incredibly friendly and welcoming, a few others could definitely use some training in hospitality and politeness. Additionally, it would be great if breakfast hours could be extended a bit later. When people are on vacation, they want to sleep in without worrying about missing the morning meal!
Reviewed on Oct 25, 2026
Adventure hotels in Key West
Southernmost Beach Resort and Guesthouses
1319 Duval Street Key West FL
Free Cancellation
Reserve now, pay when you stay
$186 nightly
The price is $210 total per night
$210 total
Oct 26 - Oct 27
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 55.90 per day. Multilingual staff at the 24-hour front desk can assist with dry cleaning/laundry, luggage storage, and tours or tickets. Other amenities at this spa hotel include free WiFi in public areas, conference space, and coffee/tea in a common area.
Pool
Spa
Hyatt Centric Key West Resort and Spa
601 Front St Key West FL
Free Cancellation
Reserve now, pay when you stay
$292 nightly
The price is $329 total per night
$329 total
Oct 26 - Oct 27
Total with taxes and fees
Guests of Hyatt Centric Key West Resort and Spa have access to a marina, a full-service spa, and an outdoor pool. Self parking is offered for USD 40 per day. Multilingual staff at the front desk are standing by 24/7 to help with luggage storage, tours or tickets, and securing valuables. 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 spa resort include a 24-hour gym, free WiFi in public areas, and a business center.
Pool
Spa
The Independent Inn-Adults only
412 Frances St Key West FL
$163 nightly
The price is $183 total per night
$183 total
Oct 26 - Oct 27
Total with taxes and fees
At The Independent Inn, guests have access to an outdoor pool, a rooftop terrace, and free WiFi in public areas. If you drive, put free parking to good use. The front desk has multilingual staff that can help with tours/tickets and luggage storage. Additional amenities include meeting rooms, coffee/tea in a common area, and a meeting room.
Pool
Parking included
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.
How much does it cost to fly to Key West?
Prices found within past 7 days. Prices and availability subject to change. Additional terms may apply.
SFB
Orlando Sanford Intl.
EYW
Key West Intl.
$78 Roundtrip, found 14 hours ago
$78
Roundtrip
found 14 hours ago
TYS
McGhee Tyson
EYW
Key West Intl.
$84 Roundtrip, found 14 hours ago
$84
Roundtrip
found 14 hours ago
PIE
St. Petersburg-Clearwater Intl.
EYW
Key West Intl.
$86 Roundtrip, found 3 hours ago
$86
Roundtrip
found 3 hours ago
AVL
Asheville Regional
EYW
Key West Intl.
$92 Roundtrip, just found
$92
Roundtrip
just found
CVG
Cincinnati - Northern Kentucky Intl.
EYW
Key West Intl.
$96 Roundtrip, found 5 days ago
$96
Roundtrip
found 5 days ago
MCO
Orlando Intl.
EYW
Key West Intl.
$102 Roundtrip, just found
$102
Roundtrip
just found
TPA
Tampa Intl.
EYW
Key West Intl.
$102 Roundtrip, just found
$102
Roundtrip
just found
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