Deals on vacations and trips to Old Town Key West

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Old Town Key West flight + hotel vacation packages

Price found within the past 48 hours. Click for updated prices.
The Key West Hotel

The Key West Hotel

3 out of 5
Key West Historic District
Price was $2,319, price is now $1,647 per person
$1,647
per person
Nov 27 - Nov 30
found 1 day ago
Roundtrip flight included
Boston (BOS) to Key West (EYW)
An outdoor pool is featured at this guesthouse, along with free WiFi in public areas and a garden. Luggage storage and concierge services are also provided.
Duval Sea Turtle by Avantstay Great Location Close to Shops Shared Pool!

Duval Sea Turtle by Avantstay Great Location Close to Shops Shared Pool!

3.5 out of 5
Old Town Key West
Price was $2,304, price is now $1,648 per person
$1,648
per person
Nov 16 - Nov 20
found 20 hours ago
Roundtrip non-stop flight included
Detroit (DTW) to Key West (EYW)
This cottage doesn't skimp on freebies - guests receive free WiFi and free self parking. An outdoor pool and concierge services are also provided.
Paradise Inn Key West - Adults Only

Paradise Inn Key West - Adults Only

3.5 out of 5
Old Town Key West
Save 100% on your flight
Price was $2,529, price is now $1,859 per person
$1,859
per person
Oct 29 - Nov 2
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Key West (EYW)
This hotel features an outdoor pool and a hot tub. Enjoy the free self-serve breakfast each morning. Self parking, a terrace, and a garden are also offered.
Casita de Catherine by Avantstay 1 Block to Duval St w/ Hot Tub!

Casita de Catherine by Avantstay 1 Block to Duval St w/ Hot Tub!

3 out of 5
Old Town Key West
Price was $2,333, price is now $1,724 per person
$1,724
per person
Nov 16 - Nov 20
found 20 hours ago
Roundtrip non-stop flight included
Detroit (DTW) to Key West (EYW)
Free WiFi in public areas is available at this cottage.
Brisa Del Mar by Avantstay Communal Pool Gated Community Ocean Front

Brisa Del Mar by Avantstay Communal Pool Gated Community Ocean Front

3 out of 5
Save 100% on your flight
Price was $3,500, price is now $2,615 per person
$2,615
per person
Nov 24 - Dec 1
found 1 day ago
Roundtrip flight included
Boston (BOS) to Key West (EYW)
An outdoor pool is featured at this cottage, along with free WiFi in public areas.

Top Old Town Key West hotels deals

Southernmost Beach Resort and Guesthouses

Southernmost Beach Resort and Guesthouses

4 out of 5
1319 Duval Street Key West FL
$225 nightly
The price is $253 total per night
$253 total
Sep 28 - Sep 29
Total with taxes and fees
A full-service spa, 3 outdoor pools, and a restaurant are all featured at this hotel. Traveling on business? Take advantage of the 2 conference rooms, along with dry cleaning/laundry services. 2 poolside bars and 2 bars/lounges are featured at this hotel, along with a gym.
Pool
Spa
Casa Marina Key West, Curio Collection by Hilton

Casa Marina Key West, Curio Collection by Hilton

4 out of 5
1500 Reynolds Street Key West FL
Free Cancellation
Reserve now, pay when you stay
$280 nightly
The price is $315 total per night
$315 total
Sep 27 - Sep 28
Total with taxes and fees
A private beach, a full-service spa, and 2 outdoor pools are all featured at this smoke-free resort. Relax with sun loungers and beach umbrellas, and cool off with a drink at the beachside bar. Enjoy the gym and perks like free WiFi.
On private beach
Pool
Southwinds Motel

Southwinds Motel

2 out of 5
1321 Simonton Street Key West FL
$155 nightly
The price is $174 total per night
$174 total
Sep 21 - Sep 22
Total with taxes and fees
This hotel features 2 outdoor pools and a bar/lounge. Enjoy the free continental breakfast each morning. Self parking, a picnic area, and luggage storage are also offered.
Pool
Breakfast included
Winslow's Bungalows - Key West Historic Inns

Winslow's Bungalows - Key West Historic Inns

4 out of 5
725 Truman Avenue Key West FL
$207 nightly
The price is $233 total per night
$233 total
Sep 23 - Sep 24
Total with taxes and fees
This smoke-free hotel features 3 outdoor pools, a bar/lounge, and a poolside bar. WiFi in public areas is free. Self parking, a garden, and luggage storage are also offered.
Pool
Pet friendly
The Reach Key West, Curio Collection by Hilton

The Reach Key West, Curio Collection by Hilton

4 out of 5
1435 Simonton Street Key West FL
Free Cancellation
Reserve now, pay when you stay
$238 nightly
The price is $267 total per night
$267 total
Sep 29 - Sep 30
Total with taxes and fees
This resort features a private beach, a full-service spa, and a restaurant. Traveling on business? Take advantage of the express check-out, laundry service, and valet parking. Enjoy the outdoor pool and unwind at the bar/lounge and poolside bar.
On private beach
Pool
Opal Key Resort & Marina, Key West

Opal Key Resort & Marina, Key West

4 out of 5
245 Front Street Key West FL
$294 nightly
The price is $331 total per night
$331 total
Sep 21 - Sep 22
Total with taxes and fees
A marina, a 24-hour gym, and a restaurant are all featured at this smoke-free hotel. Enjoy the outdoor pool and visit the 3 bars/lounges and poolside bar for drinks.
Pool
Hot Tub
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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.

Stay near popular Old Town Key West attractions

A colorful monument with text indicating it is the Southernmost Point of the Continental U.S.A. in Key West, Florida.

Southernmost Point

8.8/10 (17,214 reviews)
Snap a memorable photograph from the edge of North America at this monumental landmark.
See properties

Frequently asked questions

How much are vacation packages to Old Town Key West?
With vacation packages available from as low as $1,647, it's not necessary to blow out the credit card for your visit to Old Town Key West. Travelocity can help. Bundle hotels, flights and experiences into a package and land excellent discounts. The more you book, the more you save.
Where can I get the best vacation package deals for Old Town Key West?
With around 400 air carriers and 1,000,000 hotels across the world, it's hard to top Travelocity. Take advantage of our impressive range and pick up the best package deal to Old Town Key West. Isn't it great when trip planning is that easy?
Why should I purchase my Old Town Key West vacation package with Travelocity?
By booking your hotel, flights, activities and car rental altogether, you'll save big bucks as well as precious time. We offer round-the-clock customer support, and you'll know that you'll always be getting the best deal possible with our Price Match Guarantee. So, what's stopping you? Book your dream getaway today and get packing!
Can I save money on my Old Town Key West car rental if I combine it with my hotel or flight?
Combining your bookings into an Old Town Key West vacation package will save you a tidy sum. Combine a car and flight; a flight, car and hotel; or a hotel and car. There's no better way to explore the greater Old Town Key West region than with your own rental car. You can also add experiences and activities to your Travelocity package.
What is there to do in Old Town Key West?
While wandering about Old Town Key West, be sure to drop by South Beach and Simonton Beach. This neighborhood will keep you on your toes.

Photos of local treasures

Browse Old Town Key West vacation photos for more inspiration

A white building with shutters, palm trees, and a lawn.
A beach with palm trees, beach chairs, umbrellas, and people.
A room with wooden floors, arched windows, a chandelier, and a red rope barrier.
A sunny beach with palm trees, lounge chairs, and a building with a blue roof.
A newspaper headline 'Big Three' Proclaim V-E Day.

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