
Key West Adventure Vacation Packages

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

Heron House - Adult Only
Old Town Key West
Price was $1,329, price is now $947 per person
$947
per person
May 11 - May 14
found 1 day ago
Roundtrip non-stop flight included
Indianapolis (IND) 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.
Great stay as always
Reviewed on Apr 27, 2026

Paradise Inn Key West - Adults Only
Old Town Key West
Price was $1,461, price is now $1,011 per person
$1,011
per person
May 24 - May 27
found 10 hours ago
Roundtrip non-stop flight included
Minneapolis (MSP) to Key West (EYW)
Book a stay at this business-friendly hotel in Key West. Enjoy free breakfast, parking (surcharge), 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.
Evrryone was great- walking distance to everything. We will definitely be back.
Reviewed on Jan 3, 2026

Almond Tree Inn Hotel - Adults Only
Old Town Key West
Price was $1,660, price is now $1,187 per person
$1,187
per person
May 11 - May 14
found 1 day ago
Roundtrip non-stop flight included
Indianapolis (IND) 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 pool in our reviews. Popular attractions Duval Street and Ernest Hemingway Home and Museum are located nearby.
Danni, Rodolfo, Cary, Jack were amazing! Very kind, courteous and helpful with recommendations to restaurants etc. Clean rooms, comfortable bed you fall into a deep sleep. Amazing poolside room. Delightful breakfast, quick foods like fruit, parfaits with yogurt, bagels, boiled eggs, deli meats and cheese. Absolutely perfect!
Reviewed on Apr 28, 2026
3 night Key West Adventure vacation packages with airfare
Price found within the past 48 hours. Click for updated prices.

Heron House - Adult Only
Old Town Key West
Price was $1,329, price is now $947 per person
$947
per person
May 11 - May 14
found 1 day ago
Roundtrip non-stop flight included
Indianapolis (IND) 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.
Great stay as always
Reviewed on Apr 27, 2026

Paradise Inn Key West - Adults Only
Old Town Key West
Price was $1,461, price is now $1,011 per person
$1,011
per person
May 24 - May 27
found 10 hours ago
Roundtrip non-stop flight included
Minneapolis (MSP) to Key West (EYW)
Book a stay at this business-friendly hotel in Key West. Enjoy free breakfast, parking (surcharge), 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.
Evrryone was great- walking distance to everything. We will definitely be back.
Reviewed on Jan 3, 2026

Almond Tree Inn Hotel - Adults Only
Old Town Key West
Price was $1,660, price is now $1,187 per person
$1,187
per person
May 11 - May 14
found 1 day ago
Roundtrip non-stop flight included
Indianapolis (IND) 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 pool in our reviews. Popular attractions Duval Street and Ernest Hemingway Home and Museum are located nearby.
Danni, Rodolfo, Cary, Jack were amazing! Very kind, courteous and helpful with recommendations to restaurants etc. Clean rooms, comfortable bed you fall into a deep sleep. Amazing poolside room. Delightful breakfast, quick foods like fruit, parfaits with yogurt, bagels, boiled eggs, deli meats and cheese. Absolutely perfect!
Reviewed on Apr 28, 2026
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 $907, price is now $679 per person
$679
per person
Jul 12 - Jul 16
found 16 hours 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

Casa Marina Key West, Curio Collection by Hilton
Old Town Key West
Save 100% on your flight
Price was $1,314, price is now $919 per person
$919
per person
Jul 23 - Jul 27
found 1 day ago
Roundtrip flight included
Orlando (MCO) to Key West (EYW)
Book a stay at this beach resort in Key West. Enjoy 2 outdoor pools, a full-service spa, and a private beach. Popular attractions Duval Street and South Beach are located nearby.
Did a quick "Happy Birthday trip" for me, and had a great stay once again @ Casa! It's my fourth time, and I always feel comfortable, relaxed, and doted on while staying with them. Typically have had Kassie as a bartender, but Cassandra was just as awesome this time. If you're looking for an upscale, true relaxing destination, consider Casa Marina
Reviewed on Apr 7, 2026

The Gardens Hotel
Old Town Key West
Save 100% on your flight
Price was $1,356, price is now $974 per person
$974
per person
Jul 12 - Jul 16
found 16 hours ago
Roundtrip non-stop flight included
Boston (BOS) 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.
Paradise in paradise. Truly beautiful grounds, very special place.
Reviewed on Sep 25, 2025
5 night Key West Adventure vacation packages with airfare included
Price found within the past 48 hours. Click for updated prices.

The Gardens Hotel
Old Town Key West
Save 100% on your flight
Price was $1,714, price is now $1,194 per person
$1,194
per person
Jul 12 - Jul 17
found 1 day ago
Roundtrip non-stop flight included
Houston (IAH) 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.
Paradise in paradise. Truly beautiful grounds, very special place.
Reviewed on Sep 25, 2025

Southernmost House - Adult Exclusive
Old Town Key West
Save 100% on your flight
Price was $2,477, price is now $1,455 per person
$1,455
per person
Jun 11 - Jun 16
found 3 hours ago
Roundtrip flight included
Key West (EYW) 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 professional, courteous, and responsive.
Breakfast was very fresh, well arranged and very delicious!!!
Views of the ocean were amazing. The pool was well kept and picturesque!
Truly a wonderful experience at a first class, historic facility!
Reviewed on Oct 30, 2025

The Reach Key West, Curio Collection by Hilton
Old Town Key West
Price was $2,065, price is now $1,322 per person
$1,322
per person
May 17 - May 22
found 1 day ago
Roundtrip non-stop flight included
Minneapolis (MSP) to Key West (EYW)
Book a stay at this beach resort in Key West. Enjoy a full-service spa, a private beach, and breakfast (surcharge). Our guests praise the helpful staff and the property condition in our reviews. Popular attractions Duval Street and South Beach are located nearby.
Beautiful beach, great restaurant
Reviewed on Jan 22, 2026
Adventure vacation packages for 6-7 nights
Price found within the past 48 hours. Click for updated prices.

Heron House - Adult Only
Old Town Key West
Price was $1,531, price is now $1,096 per person
$1,096
per person
May 16 - May 22
found 10 hours ago
Roundtrip non-stop flight included
Indianapolis (IND) 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.
Great stay as always
Reviewed on Apr 27, 2026

The Gardens Hotel
Old Town Key West
Save 100% on your flight
Price was $3,513, price is now $2,265 per person
$2,265
per person
May 30 - Jun 6
found 1 day ago
Roundtrip flight included
Madison (MSN) 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.
Paradise in paradise. Truly beautiful grounds, very special place.
Reviewed on Sep 25, 2025

Orchid Key Inn - Adults Only
Old Town Key West
Save 100% on your flight
Price was $2,086, price is now $1,474 per person
$1,474
per person
May 13 - May 19
found 1 day ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) 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.
Highly recommend,great location,awesome staff!
Reviewed on Jan 2, 2026
Adventure hotels in Key West

Southernmost Beach Resort and Guesthouses
1319 Duval Street Key West FL
Free Cancellation
$283 nightly
The price is $319 total per night
$319 total
May 25 - May 26
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
Free Cancellation
Reserve now, pay when you stay
$296 nightly
The price is $333 total per night
$333 total
May 25 - May 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 concierge services, dry cleaning/laundry, 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 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
$149 nightly
The price is $167 total per night
$167 total
May 17 - May 18
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 luggage storage and tours/tickets. 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.
TPA
Tampa Intl.
EYW
Key West Intl.
$82 Roundtrip, just found
$82
Roundtrip
just found
MCO
Orlando Intl.
EYW
Key West Intl.
$102 Roundtrip, found 13 hours ago
$102
Roundtrip
found 13 hours ago
CHS
Charleston Intl.
EYW
Key West Intl.
$132 Roundtrip, found 3 days ago
$132
Roundtrip
found 3 days ago
ORF
Norfolk Intl.
EYW
Key West Intl.
$141 Roundtrip, found 8 hours ago
$141
Roundtrip
found 8 hours ago
RDU
Raleigh - Durham Intl.
EYW
Key West Intl.
$147 Roundtrip, found 2 hours ago
$147
Roundtrip
found 2 hours ago
CAK
Akron-Canton
EYW
Key West Intl.
$151 Roundtrip, found 5 days ago
$151
Roundtrip
found 5 days ago
BDL
Bradley Intl.
EYW
Key West Intl.
$156 Roundtrip, found 4 days ago
$156
Roundtrip
found 4 days ago
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