
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 $1,251, price is now $835 per person
$835
per person
May 3 - May 6
found 1 day ago
Roundtrip non-stop flight included
Augusta (AGS) 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

Heron House Court - Adult Only
Key West Historic District
Price was $1,175, price is now $853 per person
$853
per person
May 3 - May 6
found 1 day ago
Roundtrip non-stop flight included
Augusta (AGS) to Key West (EYW)
Stay at this guesthouse in Key West. Enjoy free WiFi, a rooftop terrace, and daily housekeeping. Our guests praise the breakfast and the pool in our reviews. Popular attractions Duval Street and Ernest Hemingway Home and Museum are located nearby.
Clean place and staff was accomodating. Nice breakfast.
Reviewed on Jan 5, 2026

Island City House Hotel
Key West Historic District
Price was $1,426, price is now $1,048 per person
$1,048
per person
May 3 - May 6
found 1 day ago
Roundtrip non-stop flight included
Augusta (AGS) to Key West (EYW)
Stay at this hotel in Key West. Enjoy free WiFi, a rooftop terrace, and daily housekeeping. Our guests praise the pool and the helpful staff in our reviews. Popular attractions Duval Street and Mallory Square are located nearby.
Very convenient location, clean
Reviewed on Feb 20, 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 $1,251, price is now $835 per person
$835
per person
May 3 - May 6
found 1 day ago
Roundtrip non-stop flight included
Augusta (AGS) 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

Heron House Court - Adult Only
Key West Historic District
Price was $1,175, price is now $853 per person
$853
per person
May 3 - May 6
found 1 day ago
Roundtrip non-stop flight included
Augusta (AGS) to Key West (EYW)
Stay at this guesthouse in Key West. Enjoy free WiFi, a rooftop terrace, and daily housekeeping. Our guests praise the breakfast and the pool in our reviews. Popular attractions Duval Street and Ernest Hemingway Home and Museum are located nearby.
Clean place and staff was accomodating. Nice breakfast.
Reviewed on Jan 5, 2026

Island City House Hotel
Key West Historic District
Price was $1,426, price is now $1,048 per person
$1,048
per person
May 3 - May 6
found 1 day ago
Roundtrip non-stop flight included
Augusta (AGS) to Key West (EYW)
Stay at this hotel in Key West. Enjoy free WiFi, a rooftop terrace, and daily housekeeping. Our guests praise the pool and the helpful staff in our reviews. Popular attractions Duval Street and Mallory Square are located nearby.
Very convenient location, clean
Reviewed on Feb 20, 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 $975, price is now $677 per person
$677
per person
Jul 3 - Jul 7
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

The Gardens Hotel
Old Town Key West
Save 100% on your flight
Price was $1,464, price is now $1,037 per person
$1,037
per person
Jul 3 - Jul 7
found 1 day ago
Roundtrip flight included
Atlanta (ATL) 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

The Marker Key West Harbor Resort
Key West Historic District
Save 100% on your flight
Price was $1,562, price is now $1,124 per person
$1,124
per person
Jul 3 - Jul 7
found 1 day ago
Roundtrip flight included
Atlanta (ATL) 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.
Clean rooms, amazing staff, especially Mr. Paul at the front desk, Sabrina as the conch-ierge.. house keeping, the (Kourina) bartenders. Even the espresso was great. Many thanks to all
Reviewed on Feb 26, 2026
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 $1,770, price is now $1,215 per person
$1,215
per person
Jul 3 - Jul 8
found 1 day ago
Roundtrip non-stop flight included
Jackson (JAN) 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 $2,390, price is now $1,434 per person
$1,434
per person
Jun 2 - Jun 7
found 1 day ago
Roundtrip flight included
Atlanta (ATL) 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

Almond Tree Inn Hotel - Adults Only
Old Town Key West
Save 100% on your flight
Price was $2,345, price is now $1,668 per person
$1,668
per person
May 2 - May 7
found 1 day ago
Roundtrip non-stop flight included
Fresno (FAT) 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
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 $1,207, price is now $838 per person
$838
per person
Jul 3 - Jul 9
found 1 day ago
Roundtrip non-stop flight included
Chicago (CHI) 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

Southernmost House - Adult Exclusive
Old Town Key West
Save 100% on your flight
Price was $2,579, price is now $1,433 per person
$1,433
per person
Jun 2 - Jun 8
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 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 Gardens Hotel
Old Town Key West
Save 100% on your flight
Price was $1,968, price is now $1,315 per person
$1,315
per person
Jun 2 - Jun 8
found 1 day ago
Roundtrip non-stop flight included
Cleveland (CLE) 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
Adventure hotels in Key West

Southernmost Beach Resort and Guesthouses
1319 Duval Street Key West FL
Free Cancellation
Reserve now, pay when you stay
$316 nightly
The price is $356 total per night
$356 total
May 28 - May 29
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, luggage storage, and concierge services. 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
$343 nightly
The price is $386 total per night
$386 total
May 27 - May 28
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, luggage storage, 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
$112 nightly
The price is $126 total per night
$126 total
May 10 - May 11
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 concierge services. 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.
$80 Roundtrip, found 6 days ago
$80
Roundtrip
found 6 days ago
MCO
Orlando Intl.
EYW
Key West Intl.
$98 Roundtrip, found 5 days ago
$98
Roundtrip
found 5 days ago
RDU
Raleigh - Durham Intl.
EYW
Key West Intl.
$143 Roundtrip, found 6 days ago
$143
Roundtrip
found 6 days ago
ORF
Norfolk Intl.
EYW
Key West Intl.
$144 Roundtrip, found 1 day ago
$144
Roundtrip
found 1 day ago
CAK
Akron-Canton
EYW
Key West Intl.
$148 Roundtrip, found 4 days ago
$148
Roundtrip
found 4 days ago
BDL
Bradley Intl.
EYW
Key West Intl.
$156 Roundtrip, found 5 days ago
$156
Roundtrip
found 5 days ago
PVD
T.F. Green
EYW
Key West Intl.
$205 Roundtrip, found 4 days ago
$205
Roundtrip
found 4 days ago
More to Explore
- Hotels near St. Paul's Episcopal Church
- Hotels near Key West Cemetery
- Hotels near Waterfront Playhouse
- 4 Star Hotels in Bahama Village
- 5 Star Hotels in Bahama Village
- Boutique Hotels in Bahama Village
- Golf Resorts & in Bahama Village
- Hotels with Pool in Bahama Village
- Hotels with Childcare in Bahama Village
- Hotels with Free Breakfast in Bahama Village
- Bahama Village Hotels
- Hotels near Mallory Dock
- 5 Star Hotels in Truman Annex
- White Street Gallery District Hotels
- Hotels near Mallory Square
- Hotels near Key West Lighthouse and Keeper's Quarters Museum
- Hotels near Fort Zachary Taylor Historic State Park
- Hotels near Duval Street
- Beach Resorts & in Sunset Key
- Fishing Resorts & in Sunset Key
- Hotels with Restaurants in Sunset Key
- Hotels on the Lake in Sunset Key
- Hotels on the River in Sunset Key
- Hotels with Shopping in Sunset Key
- Ski Resorts & in Sunset Key
- Sunset Key Hotels
- Hotels near Key West Shipwreck Museum
- Hotels near Custom House Museum
- Hotels near Curry Mansion Museum
- Hotels near South Beach
- 3 Star Hotels in Key West Historic District
- 4 Star Hotels in Key West Historic District
- Kid Friendly Hotels in Key West Historic District
- Golf Resorts & in Key West Historic District
- Hotels with Balconies in Key West Historic District
- Hotels with Bar in Key West Historic District
- Hotels with Free Breakfast in Key West Historic District
- Hotels with a Gym in Key West Historic District
- Hotels with Free Parking in Key West Historic District
- Pet Friendly Hotels in Key West Historic District
- Romantic Getaways & Hotels in Key West Historic District
- Ski Resorts & in Key West Historic District
- Spa Resorts & in Key West Historic District
- Key West Historic District Hotels
- Hotels near Red Barn Theater
- Hotels near Tennessee Williams Key West Exhibit
- Hotels near Audubon House and Tropical Gardens
- Hotels near Ernest Hemingway Home and Museum
- Hotels near Papa's Pilar Rum Distillery Hemingway Rum Company
- 4 Star Hotels in Fleming Key
- Apartments in Fleming Key
- Fleming Key Hotels
- Houseboats in Fleming Key
- Hotels near MLK Community Pool & Community Center
- Cheap Hotels in Old Town Key West
- Hotels with Pool in Old Town Key West
- Pet Friendly Hotels in Old Town Key West
- Old Town Key West Hotels
- 5 Star Hotels in Historic Seaport
- Beach Resorts & in Historic Seaport
- Historic Seaport Hotels
- Hotels near Simonton Beach
- Hotels near Florida Keys Eco - Discovery Center
- Hotels near Key West Butterfly and Nature Conservatory
- Hotels near Harry S. Truman Little White House
- Hotels near Clarence S. Higgs Memorial Beach Park
- Hotels near Donkey Milk House
- Meadows Hotels
- Cheap Hotels in Downtown Key West
- Hotels with Pool in Downtown Key West
- Pet Friendly Hotels in Downtown Key West
- Hotels near Florida Keys National Marine Sanctuary
- Hotels near Southernmost Point
- Hotels near Oldest House Museum and Garden
- Hotels near Jackson Square
- Fort Zachary Taylor Historic State Park
- Duval Street
- Sails To Rails Museum at Flagler Station
- Ernest Hemingway Home and Museum
- San Carlos Institute - Casa Cuba
- Mlk Community Pool & Community Center
- Florida Keys Eco - Discovery Center
- Key West Butterfly and Nature Conservatory
- The Kite House
- Donkey Milk House
- Southernmost Point
- Alamo Rent A Car Rental Cars in Sunset Key
- Avis Rental Cars in Sunset Key
- Budget Rental Cars in Sunset Key
- Car rentals near Sunset Key
- Enterprise Rental Cars in Sunset Key
- Hertz Rental Cars in Sunset Key
- Nü Car Rentals Rental Cars in Sunset Key
- National Car Rental Rental Cars in Sunset Key
- Payless Rental Cars in Sunset Key
- Sixt Rental Cars in Sunset Key
- Thrifty Car Rental Rental Cars in Sunset Key
- Car rentals near Key West Historic District
- Car rentals near Uptown - Upper Duval

