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 Perry Hotel & Marina Key West

The Perry Hotel & Marina Key West

4 out of 5
Save 100% on your flight
Price was $1,131, price is now $761 per person
$761
per person
Sep 19 - Sep 26
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Key West (EYW)
A marina, 2 restaurants, and 2 outdoor pools are all featured at this smoke-free hotel. Traveling for business? Take advantage of the free WiFi in public areas, laundry service, and conference space. 2 poolside bars and 2 bars/lounges are featured at this hotel, along with a 24-hour gym.
Ibis Bay Beach Resort

Ibis Bay Beach Resort

2.5 out of 5
Northside Resort
Save 100% on your flight
Price was $1,370, price is now $846 per person
$846
per person
Sep 19 - Sep 26
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Key West (EYW)
This Art Deco hotel features a private beach, a marina, and a restaurant. Enjoy a day at the beach kayaking, or relax with sun loungers. Enjoy the outdoor pool and free perks like continental breakfast and WiFi in public areas.
The Key West Hotel

The Key West Hotel

3 out of 5
Key West Historic District
Save 100% on your flight
Price was $2,762, price is now $1,756 per person
$1,756
per person
Sep 19 - Sep 26
found 1 day ago
Roundtrip flight included
Atlanta (ATL) 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.
Coconut Beach Resort

Coconut Beach Resort

2.5 out of 5
Old Town Key West
Save 100% on your flight
Price was $2,292, price is now $1,588 per person
$1,588
per person
Sep 19 - Sep 26
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Key West (EYW)
A private beach and an outdoor pool are featured at this smoke-free resort. Enjoy the hot tub and perks like free self parking and free WiFi. A computer station, dry cleaning, and luggage storage are also on offer.
Southernmost House - Adult Exclusive

Southernmost House - Adult Exclusive

4 out of 5
Old Town Key West
Price was $2,555, price is now $1,799 per person
$1,799
per person
Aug 13 - Aug 16
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Key West (EYW)
This hotel features a restaurant, an outdoor pool, and a bar/lounge. Guests will appreciate free perks like cooked-to-order breakfast and WiFi in public areas. Self parking, a terrace, and a picnic area are also offered.

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
Free Cancellation
Reserve now, pay when you stay
$218 nightly
The price is $245 total per night
$245 total
Aug 11 - Aug 12
Total with taxes and fees
This hotel features a full-service spa, 3 outdoor pools, and a restaurant. Enjoy beachfront dining and relax with sun loungers and beach umbrellas. Traveling on business? Take advantage of the 2 conference rooms, along with dry cleaning/laundry services.
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
$259 nightly
The price is $291 total per night
$291 total
Jul 16 - Jul 17
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.
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
$252 nightly
The price is $283 total per night
$283 total
Aug 11 - Aug 12
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.
Southwinds Motel

Southwinds Motel

2 out of 5
1321 Simonton Street Key West FL
$145 nightly
The price is $164 total per night
$164 total
Aug 10 - Aug 11
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
The Southernmost Inn - Adults Only

The Southernmost Inn - Adults Only

3 out of 5
525 United Street Key West FL
Free Cancellation
Reserve now, pay when you stay
$162 nightly
The price is $182 total per night
$182 total
Jul 16 - Jul 17
Total with taxes and fees
This hotel's 2 outdoor pools and hot tub are among the featured amenities. Enjoy the free continental breakfast each morning. Self parking, a coffee shop, and a terrace are also offered.
Douglas House - Adults Only

Douglas House - Adults Only

3 out of 5
419 Amelia St Key West FL
$148 nightly
The price is $166 total per night
$166 total
Jul 20 - Jul 21
Total with taxes and fees
An outdoor pool is featured at this guesthouse, along with free WiFi in public areas and a terrace. A garden, a picnic area, and luggage storage are also on offer.
Pool
Free WiFi
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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 $761, 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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