
Key West Adventure Vacation Packages

Best Key West Adventure packages
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 $1,151, price is now $750 per person
$750
per person
Feb 24 - Feb 27
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Key West (EYW)
Book a stay at this 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.
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

Ella's Cottages - Key West Historic Inns
Old Town Key West
Save 100% on your flight
Price was $1,759, price is now $1,269 per person
$1,269
per person
Jan 24 - Jan 27
found 1 day ago
Roundtrip non-stop flight included
Birmingham (BHM) to Key West (EYW)
Book a stay at this 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

Southernmost Beach Resort and Guesthouses
Old Town Key West
Save 100% on your flight
Price was $1,516, price is now $1,120 per person
$1,120
per person
Feb 24 - Feb 27
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Key West (EYW)
Book a stay at this beach hotel in Key West. Enjoy free WiFi, 3 outdoor pools, and a full-service spa. Our guests praise the pool and the helpful staff in our reviews. Popular attractions Duval Street and Southernmost Point are located nearby.
Billed me for parking when I didn’t have a car. Took several calls to try and resolve. Still haven’t received a refund. They were quick to take my money when I paid for the room but not so responsive in processing my refund.
Reviewed on Nov 1, 2025
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
Save 100% on your flight
Price was $1,151, price is now $750 per person
$750
per person
Feb 24 - Feb 27
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Key West (EYW)
Book a stay at this 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.
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

Ella's Cottages - Key West Historic Inns
Old Town Key West
Save 100% on your flight
Price was $1,759, price is now $1,269 per person
$1,269
per person
Jan 24 - Jan 27
found 1 day ago
Roundtrip non-stop flight included
Birmingham (BHM) to Key West (EYW)
Book a stay at this 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

Southernmost Beach Resort and Guesthouses
Old Town Key West
Save 100% on your flight
Price was $1,516, price is now $1,120 per person
$1,120
per person
Feb 24 - Feb 27
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Key West (EYW)
Book a stay at this beach hotel in Key West. Enjoy free WiFi, 3 outdoor pools, and a full-service spa. Our guests praise the pool and the helpful staff in our reviews. Popular attractions Duval Street and Southernmost Point are located nearby.
Billed me for parking when I didn’t have a car. Took several calls to try and resolve. Still haven’t received a refund. They were quick to take my money when I paid for the room but not so responsive in processing my refund.
Reviewed on Nov 1, 2025
4 night Key West Adventure vacation packages with flight
Price found within the past 48 hours. Click for updated prices.

Heron House - Adult Only
Old Town Key West
Price was $1,496, price is now $1,028 per person
$1,028
per person
Jan 26 - Jan 30
just found
Roundtrip non-stop flight included
Pensacola (PNS) to Key West (EYW)
Stay at this B&B in Key West. Enjoy free breakfast, free WiFi, and a rooftop terrace. Our guests praise the breakfast and the pool in our reviews. Popular attractions Duval Street and Ernest Hemingway Home and Museum are located nearby.
Very unique place!!!
Reviewed on Sep 16, 2025

Oceans Edge Key West Resort, Hotel & Marina
Save 100% on your flight
Price was $2,689, price is now $1,689 per person
$1,689
per person
Jan 24 - Jan 28
found 1 day ago
Roundtrip flight included
Boston (BOS) to Key West (EYW)
Book a stay at this 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.
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

Ella's Cottages - Key West Historic Inns
Old Town Key West
Save 100% on your flight
Price was $2,366, price is now $1,654 per person
$1,654
per person
Jan 24 - Jan 28
found 1 day ago
Roundtrip flight included
Boston (BOS) to Key West (EYW)
Book a stay at this 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
5 night Key West Adventure vacation packages with airfare included
Price found within the past 48 hours. Click for updated prices.

Fitch Lodge - Key West Historic Inns
Key West Historic District
Save 100% on your flight
Price was $1,799, price is now $1,188 per person
$1,188
per person
Mar 27 - Apr 1
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Key West (EYW)
Stay at this hotel in Key West. Enjoy free breakfast, free WiFi, and daily housekeeping. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Duval Street and Mallory Square are located nearby.
My only complaint is. “Pet friendly” property shouldn’t charge $100 to bring said pet. A deposit fine, but otherwise it’s ripoff
Reviewed on Jun 21, 2024

Oceans Edge Key West Resort, Hotel & Marina
Save 100% on your flight
Price was $2,305, price is now $1,344 per person
$1,344
per person
Mar 27 - Apr 1
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Key West (EYW)
Book a stay at this 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.
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

Lighthouse Hotel - Key West Historic Inns
Old Town Key West
Save 100% on your flight
Price was $1,989, price is now $1,300 per person
$1,300
per person
Mar 27 - Apr 1
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Key West (EYW)
Stay at this hotel in Key West. Enjoy free breakfast, free WiFi, and daily housekeeping. Our guests praise the helpful staff in our reviews. Popular attractions Duval Street and Ernest Hemingway Home and Museum are located nearby.
The rooms ideally could have been a bit cleaner. For instance vacuum underneath the furnishings. Great breakfast and the loft room
Was fantastic. Close to everything yet not in the congestion.
Reviewed on Jan 15, 2026
Adventure vacation packages for 6-7 nights
Price found within the past 48 hours. Click for updated prices.

Lighthouse Hotel - Key West Historic Inns
Old Town Key West
Save 100% on your flight
Price was $3,344, price is now $2,295 per person
$2,295
per person
Feb 24 - Mar 2
found 24 hours ago
Roundtrip non-stop flight included
Burlington (BTV) to Key West (EYW)
Stay at this hotel in Key West. Enjoy free breakfast, free WiFi, and daily housekeeping. Our guests praise the helpful staff in our reviews. Popular attractions Duval Street and Ernest Hemingway Home and Museum are located nearby.
The rooms ideally could have been a bit cleaner. For instance vacuum underneath the furnishings. Great breakfast and the loft room
Was fantastic. Close to everything yet not in the congestion.
Reviewed on Jan 15, 2026

Oceans Edge Key West Resort, Hotel & Marina
Save 100% on your flight
Price was $4,660, price is now $2,620 per person
$2,620
per person
Jan 24 - Jan 31
found 1 day ago
Roundtrip non-stop flight included
Detroit (DTT) to Key West (EYW)
Book a stay at this 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.
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

Pier House Resort & Spa
Key West Historic District
Save 100% on your flight
Price was $3,636, price is now $2,484 per person
$2,484
per person
Mar 27 - Apr 2
found 1 day ago
Roundtrip flight included
Chicago (CHI) to Key West (EYW)
Book a stay at this beach resort in Key West. Enjoy a full-service spa, a private beach, and 2 bars/lounges. Our guests praise the pool and the helpful staff 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
Adventure hotels in Key West

Southernmost Beach Resort and Guesthouses
1319 Duval Street Key West FL
Free Cancellation
$530 nightly
The price is $596 total per night
$596 total
Jan 26 - Jan 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 53.75 per day. Multilingual staff at the 24-hour front desk can assist with dry cleaning/laundry, tours or tickets, and luggage storage. Other amenities at this beach hotel include conference space, coffee/tea in a common area, and a computer station.
Pool
Spa

Hyatt Centric Key West Resort and Spa
601 Front St Key West FL
$502 nightly
The price is $564 total per night
$564 total
Jan 25 - Jan 26
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 securing valuables, dry cleaning/laundry, and luggage storage. 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
$313 nightly
The price is $352 total per night
$352 total
Jan 27 - Jan 28
Total with taxes and fees
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 concierge services 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.
$102 Roundtrip, found 2 hours ago
$102
Roundtrip
found 2 hours ago
TPA
Tampa Intl.
EYW
Key West Intl.
$110 Roundtrip, found 1 hour ago
$110
Roundtrip
found 1 hour ago
FLL
Fort Lauderdale - Hollywood Intl.
EYW
Key West Intl.
$120 Roundtrip, just found
$120
Roundtrip
just found
ORF
Norfolk Intl.
EYW
Key West Intl.
$121 Roundtrip, found 2 days ago
$121
Roundtrip
found 2 days ago
ATL
Hartsfield-Jackson Atlanta Intl.
EYW
Key West Intl.
$128 Roundtrip, found 1 day ago
$128
Roundtrip
found 1 day ago
CAK
Akron-Canton
EYW
Key West Intl.
$133 Roundtrip, found 6 days ago
$133
Roundtrip
found 6 days ago
BOS
Logan Intl.
EYW
Key West Intl.
$154 Roundtrip, found 3 hours ago
$154
Roundtrip
found 3 hours ago
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