
Key West Adventure Vacation Packages
Best Key West Adventure packages
Price found within the past 48 hours. Click for updated prices.

Almond Tree Inn Hotel - Adults Only
Old Town Key West
Price was $938, price is now $712 per person
$712
per person
Aug 31 - Sep 3
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Key West (EYW)
Stay at this 3.5-star business-friendly hotel in Key West. Enjoy free breakfast, free WiFi, and parking (surcharge). Our guests praise the breakfast and the pool in our reviews. Popular attractions Duval Street and Ernest Hemingway Home and Museum are located nearby.
As always, Almond Tree Inn was a bright spot in our latest trip to Key West. I’ve stayed here several times over the years and everything about Almond Tree is top notch, from the superbly attentive and friendly staff to the well-appointed and maintained property. You always feel special staying here and this trip was no exception. As Florida locals, we look forward to our stays with you each and every time- THANK YOU!
Reviewed on May 26, 2025

Lighthouse Hotel - Key West Historic Inns
Old Town Key West
Save 100% on your flight
Price was $1,027, price is now $756 per person
$756
per person
Aug 31 - Sep 3
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Key West (EYW)
Stay at this 3.5-star hotel in Key West. Enjoy free breakfast, free WiFi, and daily housekeeping. Our guests praise the helpful staff and the property condition in our reviews. Popular attractions Duval Street and Ernest Hemingway Home and Museum are located nearby.
This place is a much better place to stay than places closer to the cruise ship pier or off or whitehead or duval
Reviewed on Sep 22, 2024

Ella's Cottages - Key West Historic Inns
Old Town Key West
Price was $2,112, price is now $1,716 per person
$1,716
per person
Aug 29 - Sep 1
found 13 hours ago
Roundtrip non-stop flight included
Albany (ALB) to Key West (EYW)
Stay at this 3.5-star business-friendly hotel in Key West. Enjoy free breakfast, free WiFi, and parking (surcharge). Our guests praise the breakfast and the helpful staff in our reviews. Popular attractions Duval Street and Ernest Hemingway Home and Museum are located nearby.
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
3 night Key West Adventure vacation packages with airfare
Price found within the past 48 hours. Click for updated prices.

Oceans Edge Key West Resort, Hotel & Marina
Price was $780, price is now $552 per person
$552
per person
Oct 30 - Nov 2
found 1 day ago
Roundtrip non-stop flight included
Columbia (CAE) to Key West (EYW)
Stay at this 4-star luxury hotel in Key West. Enjoy free WiFi, 6 outdoor pools, and a marina. Our guests praise the pool and the restaurant in our reviews. Popular attractions Duval Street and Smathers Beach are located nearby.
Great area for the cost. Very clean and inviting. Room had a water harbor view which was nice.
Reviewed on Jul 12, 2025

Lighthouse Hotel - Key West Historic Inns
Old Town Key West
Save 100% on your flight
Price was $1,368, price is now $775 per person
$775
per person
Oct 30 - Nov 2
found 1 day ago
Roundtrip non-stop flight included
Columbia (CAE) to Key West (EYW)
Stay at this 3.5-star hotel in Key West. Enjoy free breakfast, free WiFi, and daily housekeeping. Our guests praise the helpful staff and the property condition in our reviews. Popular attractions Duval Street and Ernest Hemingway Home and Museum are located nearby.
This place is a much better place to stay than places closer to the cruise ship pier or off or whitehead or duval
Reviewed on Sep 22, 2024

Pier House Resort & Spa
Key West Historic District
Save 100% on your flight
Price was $1,251, price is now $911 per person
$911
per person
Oct 30 - Nov 2
found 1 day ago
Roundtrip non-stop flight included
Columbia (CAE) to Key West (EYW)
Stay at this 4-star beach resort in Key West. Enjoy a full-service spa, a private beach, and 2 bars/lounges. Our guests praise the pool and the bar in our reviews. Popular attractions Duval Street and Mallory Square are located nearby.
This is a wonderful resort in Key West that has great amenities and located on Duval Street! Highly recommend.
Reviewed on Jun 24, 2025
4 night Key West Adventure vacation packages with flight
Price found within the past 48 hours. Click for updated prices.

Oceans Edge Key West Resort, Hotel & Marina
Price was $1,027, price is now $743 per person
$743
per person
Oct 30 - Nov 3
found 19 hours ago
Roundtrip non-stop flight included
Chicago (CHI) to Key West (EYW)
Stay at this 4-star luxury hotel in Key West. Enjoy free WiFi, 6 outdoor pools, and a marina. Our guests praise the pool and the restaurant in our reviews. Popular attractions Duval Street and Smathers Beach are located nearby.
Great area for the cost. Very clean and inviting. Room had a water harbor view which was nice.
Reviewed on Jul 12, 2025

Lighthouse Hotel - Key West Historic Inns
Old Town Key West
Save 100% on your flight
Price was $1,347, price is now $925 per person
$925
per person
Oct 30 - Nov 3
found 19 hours ago
Roundtrip non-stop flight included
Chicago (CHI) to Key West (EYW)
Stay at this 3.5-star hotel in Key West. Enjoy free breakfast, free WiFi, and daily housekeeping. Our guests praise the helpful staff and the property condition in our reviews. Popular attractions Duval Street and Ernest Hemingway Home and Museum are located nearby.
This place is a much better place to stay than places closer to the cruise ship pier or off or whitehead or duval
Reviewed on Sep 22, 2024

Orchid Key Inn - Adults Only
Old Town Key West
Save 100% on your flight
Price was $1,888, price is now $1,347 per person
$1,347
per person
Oct 30 - Nov 3
found 19 hours ago
Roundtrip non-stop flight included
Chicago (CHI) to Key West (EYW)
Stay at this 3.5-star hotel in Key West. Enjoy free breakfast, free WiFi, and parking (surcharge). Our guests praise the breakfast and the pool in our reviews. Popular attractions Duval Street and Ernest Hemingway Home and Museum are located nearby.
This is a great place to relax, great breakfast, pool, bar, steps away from everything on Duval. I would give it a perfect score other than Alex the bartender being a little….let’s call it snitty. We would stay here again.
Reviewed on Aug 1, 2025
5 night Key West Adventure vacation packages with airfare included
Price found within the past 48 hours. Click for updated prices.

Oceans Edge Key West Resort, Hotel & Marina
Save 100% on your flight
Price was $999, price is now $639 per person
$639
per person
Oct 30 - Nov 4
found 6 hours ago
Roundtrip flight included
Wilkes-Barre (AVP) to Key West (EYW)
Stay at this 4-star luxury hotel in Key West. Enjoy free WiFi, 6 outdoor pools, and a marina. Our guests praise the pool and the restaurant in our reviews. Popular attractions Duval Street and Smathers Beach are located nearby.
Great area for the cost. Very clean and inviting. Room had a water harbor view which was nice.
Reviewed on Jul 12, 2025

Lighthouse Hotel - Key West Historic Inns
Old Town Key West
Save 100% on your flight
Price was $1,382, price is now $830 per person
$830
per person
Oct 30 - Nov 4
found 6 hours ago
Roundtrip flight included
Wilkes-Barre (AVP) to Key West (EYW)
Stay at this 3.5-star hotel in Key West. Enjoy free breakfast, free WiFi, and daily housekeeping. Our guests praise the helpful staff and the property condition in our reviews. Popular attractions Duval Street and Ernest Hemingway Home and Museum are located nearby.
This place is a much better place to stay than places closer to the cruise ship pier or off or whitehead or duval
Reviewed on Sep 22, 2024

Ibis Bay Beach Resort
Northside Resort
Save 100% on your flight
Price was $1,311, price is now $889 per person
$889
per person
Oct 30 - Nov 4
found 6 hours ago
Roundtrip flight included
Wilkes-Barre (AVP) to Key West (EYW)
Book a stay at this beach hotel in Key West. Enjoy free breakfast, free WiFi, and a private beach. Our guests praise the breakfast and the pool in our reviews. Popular attractions Duval Street and Smathers Beach are located nearby.
Room was very small. Window shade wouldn't block the light beaming in my window all night. Not that big of a deal though, i wasn't there for the room. The beach was pretty much rock, so that wasn't great. The facilities offer plenty for you. Bar, restaurant, boat rentals. Tours. My favorite was probably be the hammocks a plenty
Reviewed on Jul 15, 2025
Adventure vacation packages for 6-7 nights
Price found within the past 48 hours. Click for updated prices.

Oceans Edge Key West Resort, Hotel & Marina
Save 100% on your flight
Price was $1,159, price is now $754 per person
$754
per person
Aug 29 - Sep 5
found 18 hours ago
Roundtrip non-stop flight included
Boston (BOS) to Key West (EYW)
Stay at this 4-star luxury hotel in Key West. Enjoy free WiFi, 6 outdoor pools, and a marina. Our guests praise the pool and the restaurant in our reviews. Popular attractions Duval Street and Smathers Beach are located nearby.
Great area for the cost. Very clean and inviting. Room had a water harbor view which was nice.
Reviewed on Jul 12, 2025

Orchid Key Inn - Adults Only
Old Town Key West
Save 100% on your flight
Price was $2,178, price is now $1,393 per person
$1,393
per person
Sep 29 - Oct 6
found 1 day ago
Roundtrip flight included
Fort Wayne (FWA) to Key West (EYW)
Stay at this 3.5-star hotel in Key West. Enjoy free breakfast, free WiFi, and parking (surcharge). Our guests praise the breakfast and the pool in our reviews. Popular attractions Duval Street and Ernest Hemingway Home and Museum are located nearby.
This is a great place to relax, great breakfast, pool, bar, steps away from everything on Duval. I would give it a perfect score other than Alex the bartender being a little….let’s call it snitty. We would stay here again.
Reviewed on Aug 1, 2025

Southernmost Beach Resort and Guesthouses
Old Town Key West
Save 100% on your flight
Price was $1,542, price is now $1,061 per person
$1,061
per person
Sep 29 - Oct 6
found 1 day ago
Roundtrip flight included
Fort Wayne (FWA) to Key West (EYW)
Stay at this 4-star beach hotel in Key West. Enjoy free WiFi, 3 outdoor pools, and a full-service spa. Our guests praise the pool and the bar in our reviews. Popular attractions Duval Street and South Beach are located nearby.
We visited in July and were able to upgrade to an oceanfront room with a balcony. If you get the chance, it’s worth it! Pools are beautiful and food and drinks are offered poolside. The view was incredible! The staff were all incredibly accommodating and friendly!! We can’t wait to come back!!
Reviewed on Aug 1, 2025
Adventure hotels in Key West

Southernmost Beach Resort and Guesthouses
1319 Duval Street, Key West, FL
Free Cancellation
The price is $258 total per night
$258 total
per night
Sep 8 - Sep 9
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 47 per day. Multilingual staff at the 24-hour front desk can assist with concierge services, luggage storage, and dry cleaning/laundry. Other amenities at this beach hotel include conference space, a 24-hour business center, 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
The price is $261 total per night
$261 total
per night
Sep 7 - Sep 8
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 tours or tickets, securing valuables, 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 resort include a 24-hour gym, free WiFi in public areas, and a business center.
Pool
Spa

Heron House Court - Adult Only
412 Frances St, Key West, FL
The price is $154 total per night
$154 total
per night
Aug 27 - Aug 28
At Heron House Court - Adult Only, guests have access to an outdoor pool, a rooftop terrace, and free WiFi in public areas. The front desk has multilingual staff that can help with tours/tickets and luggage storage. Other amenities at this adults-only guesthouse include coffee/tea in a common area, a terrace, and a garden.
Pool
Free WiFi
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.
MCO
Orlando Intl.
EYW
Key West Intl.
$122 Roundtrip, found 5 hours ago
$122
Roundtrip
found 5 hours ago
TPA
Tampa Intl.
EYW
Key West Intl.
$122 Roundtrip, just found
$122
Roundtrip
just found
CAK
Akron-Canton
EYW
Key West Intl.
$148 Roundtrip, found 4 days ago
$148
Roundtrip
found 4 days ago
FLL
Fort Lauderdale - Hollywood Intl.
EYW
Key West Intl.
$158 Roundtrip, found 5 hours ago
$158
Roundtrip
found 5 hours ago
BOS
Logan Intl.
EYW
Key West Intl.
$171 Roundtrip, found 6 days ago
$171
Roundtrip
found 6 days ago
PIT
Pittsburgh Intl.
EYW
Key West Intl.
$201 Roundtrip, found 5 days ago
$201
Roundtrip
found 5 days ago
PVD
T.F. Green
EYW
Key West Intl.
$231 Roundtrip, found 4 days ago
$231
Roundtrip
found 4 days ago