
Key West Adventure Vacation Packages

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

Fitch Lodge - Key West Historic Inns
Key West Historic District
Price was $735, price is now $580 per person
$580
per person
Sep 1 - Sep 5
found 8 hours ago
Roundtrip non-stop flight included
Cleveland (CLE) to Key West (EYW)
Stay at this hotel in Key West. Enjoy free WiFi, daily housekeeping, and concierge services. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Duval Street and Southernmost Point are located nearby.
The two from desk staffmembers were so friendly and helpful!
Reviewed on Jul 26, 2026

Ibis Bay Beach Resort
Northside Resort
Price was $968, price is now $757 per person
$757
per person
Aug 1 - Aug 4
found 23 hours ago
Roundtrip non-stop flight included
Hartford (BDL) 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 Southernmost Point are located nearby.
.
Reviewed on Jul 28, 2026

Heron House - Adult Only
Old Town Key West
Price was $1,061, price is now $835 per person
$835
per person
Aug 2 - Aug 5
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) 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.
Our room was very spacious, very clean and inviting, The property itself is amazing! Breakfast and coffee bar was simple but totally enough! Everyone was so kind and helpful. This was an excellent location and we will definitely stay again.
Reviewed on Jul 28, 2026
3 night Key West Adventure vacation packages with airfare
Price found within the past 48 hours. Click for updated prices.

Ibis Bay Beach Resort
Northside Resort
Price was $968, price is now $757 per person
$757
per person
Aug 1 - Aug 4
found 23 hours ago
Roundtrip non-stop flight included
Hartford (BDL) 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 Southernmost Point are located nearby.
.
Reviewed on Jul 28, 2026

Pier House Resort & Spa
Key West Historic District
Price was $1,077, price is now $792 per person
$792
per person
Oct 2 - Oct 5
found 1 day ago
Roundtrip flight included
Atlanta (ATL) 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 Southernmost Point are located nearby.

Heron House - Adult Only
Old Town Key West
Price was $1,061, price is now $835 per person
$835
per person
Aug 2 - Aug 5
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) 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.
Our room was very spacious, very clean and inviting, The property itself is amazing! Breakfast and coffee bar was simple but totally enough! Everyone was so kind and helpful. This was an excellent location and we will definitely stay again.
Reviewed on Jul 28, 2026
4 night Key West Adventure vacation packages with flight
Price found within the past 48 hours. Click for updated prices.

Ibis Bay Beach Resort
Northside Resort
Save 100% on your flight
Price was $972, price is now $650 per person
$650
per person
Sep 1 - Sep 5
found 1 day ago
Roundtrip non-stop flight included
Cleveland (CLE) 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 Southernmost Point are located nearby.
.
Reviewed on Jul 28, 2026

Pier House Resort & Spa
Key West Historic District
Save 100% on your flight
Price was $1,253, price is now $894 per person
$894
per person
Oct 2 - Oct 6
found 4 hours ago
Roundtrip flight included
Atlanta (ATL) 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 Southernmost Point are located nearby.

The Gardens Hotel
Old Town Key West
Save 100% on your flight
Price was $2,046, price is now $1,498 per person
$1,498
per person
Oct 2 - Oct 6
found 16 hours ago
Roundtrip non-stop flight included
Cincinnati (CVG) 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 Southernmost Point are located nearby.
Nice location/ambient and front desk staff, only reason for not providing 5 stars is because bed was not really comfortable and the lady serving breakfast wasn't rude but not friendly as a server position, specially to begins the day journey.
Reviewed on Jul 28, 2026
5 night Key West Adventure vacation packages with airfare included
Price found within the past 48 hours. Click for updated prices.

Ibis Bay Beach Resort
Northside Resort
Save 100% on your flight
Price was $1,226, price is now $802 per person
$802
per person
Sep 1 - Sep 6
found 19 hours ago
Roundtrip flight included
Chicago (ORD) 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 Southernmost Point are located nearby.
.
Reviewed on Jul 28, 2026

Ella's Cottages - Key West Historic Inns
Old Town Key West
Save 100% on your flight
Price was $1,224, price is now $875 per person
$875
per person
Oct 2 - Oct 7
found 1 day ago
Roundtrip non-stop flight included
Newark Liberty Intl. Airport (EWR) 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.
S
Reviewed on Jul 15, 2026

Pier House Resort & Spa
Key West Historic District
Save 100% on your flight
Price was $1,469, price is now $1,054 per person
$1,054
per person
Oct 2 - Oct 7
found 1 day ago
Roundtrip non-stop flight included
Newark Liberty Intl. Airport (EWR) 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 Southernmost Point are located nearby.
Adventure vacation packages for 6-7 nights
Price found within the past 48 hours. Click for updated prices.

Ibis Bay Beach Resort
Northside Resort
Price was $1,331, price is now $926 per person
$926
per person
Aug 1 - Aug 7
found 11 hours ago
Roundtrip non-stop flight included
Durango (DRO) 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 Southernmost Point are located nearby.
.
Reviewed on Jul 28, 2026

Lighthouse Hotel - Key West Historic Inns
Old Town Key West
Save 100% on your flight
Price was $1,486, price is now $992 per person
$992
per person
Oct 2 - Oct 8
found 1 day ago
Roundtrip non-stop flight included
Nashville (BNA) 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.

Pier House Resort & Spa
Key West Historic District
Save 100% on your flight
Price was $1,735, price is now $1,231 per person
$1,231
per person
Oct 2 - Oct 8
found 1 day ago
Roundtrip non-stop flight included
Nashville (BNA) 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 Southernmost Point are located nearby.
Adventure hotels in Key West

Southernmost Beach Resort and Guesthouses
1319 Duval Street Key West FL
Free Cancellation
Reserve now, pay when you stay
$210 nightly
The price is $237 total per night
$237 total
Aug 18 - Aug 19
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, luggage storage, and dry cleaning/laundry. Other amenities at this beach hotel include conference space, coffee/tea in a common area, and a computer station.

Hyatt Centric Key West Resort and Spa
601 Front St Key West FL
Free Cancellation
Reserve now, pay when you stay
$261 nightly
The price is $294 total per night
$294 total
Aug 10 - Aug 11
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 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.

The Independent Inn - Locally Owned
412 Frances St Key West FL
$152 nightly
The price is $167 total per night
$167 total
Aug 9 - Aug 10
Total with taxes and fees
At The Independent Inn - Locally Owned, 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. Additional amenities 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.
SFB
Orlando Sanford Intl.
EYW
Key West Intl.
$78 Roundtrip, found 6 hours ago
$78
Roundtrip
found 6 hours ago
TPA
Tampa Intl.
EYW
Key West Intl.
$82 Roundtrip, found 8 hours ago
$82
Roundtrip
found 8 hours ago
TYS
McGhee Tyson
EYW
Key West Intl.
$84 Roundtrip, found 2 days ago
$84
Roundtrip
found 2 days ago
PIE
St. Petersburg-Clearwater Intl.
EYW
Key West Intl.
$86 Roundtrip, just found
$86
Roundtrip
just found
AVL
Asheville Regional
EYW
Key West Intl.
$92 Roundtrip, found 10 hours ago
$92
Roundtrip
found 10 hours ago
CVG
Cincinnati - Northern Kentucky Intl.
EYW
Key West Intl.
$96 Roundtrip, just found
$96
Roundtrip
just found
MCO
Orlando Intl.
EYW
Key West Intl.
$102 Roundtrip, just found
$102
Roundtrip
just found
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