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.
Paradise Inn Key West - Adults Only

Paradise Inn Key West - Adults Only

3.5 out of 5
Old Town Key West
Price was $1,484, price is now $1,050 per person
$1,050
per person
Jan 19 - Jan 22
found 1 day ago
Roundtrip non-stop flight included
Detroit (DTW) 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.
The Key West Hotel

The Key West Hotel

3 out of 5
Key West Historic District
Price was $2,191, price is now $1,461 per person
$1,461
per person
Jan 18 - Jan 21
found 1 day ago
Roundtrip non-stop flight included
Detroit (DTW) 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.
Orchid Key Inn - Adults Only

Orchid Key Inn - Adults Only

3.5 out of 5
Old Town Key West
Price was $2,564, price is now $1,827 per person
$1,827
per person
Dec 24 - Dec 28
found 1 day ago
Roundtrip non-stop flight included
Detroit (DTW) to Key West (EYW)
This hotel features a bar/lounge, a poolside bar, and an outdoor pool. Enjoy the hot tub and free continental breakfast each morning. Self parking, a garden, and dry cleaning are also offered.
Tropical Dreaming by Avantstay 4 Blks to Beach! Private Pool!

Tropical Dreaming by Avantstay 4 Blks to Beach! Private Pool!

3 out of 5
Old Town Key West
Price was $6,287, price is now $4,522 per person
$4,522
per person
Jan 10 - Jan 17
found 13 hours ago
Roundtrip non-stop flight included
Detroit (DTW) to Key West (EYW)
An outdoor pool is featured at this cottage, along with free WiFi in public areas.
Seascape Tropical Inn - Adult Exclusive

Seascape Tropical Inn - Adult Exclusive

3 out of 5
Old Town Key West
Price was $1,574, price is now $1,133 per person
$1,133
per person
Jan 19 - Jan 22
found 1 day ago
Roundtrip non-stop flight included
Detroit (DTW) to Key West (EYW)
Free WiFi in public areas, a terrace, and a garden are available at this bed & breakfast. Enjoy the free continental breakfast each morning. Luggage storage and concierge services are also provided.

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
$264 nightly
The price is $297 total per night
$297 total
Nov 15 - Nov 16
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, free WiFi in public areas, and laundry service. 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
$270 nightly
The price is $304 total per night
$304 total
Nov 23 - Nov 24
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
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
$229 nightly
The price is $258 total per night
$258 total
Dec 1 - Dec 2
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.
Pool
Hot Tub
Winslow's Bungalows - Key West Historic Inns

Winslow's Bungalows - Key West Historic Inns

4 out of 5
725 Truman Avenue Key West FL
$245 nightly
The price is $276 total per night
$276 total
Nov 30 - Dec 1
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
$280 nightly
The price is $315 total per night
$315 total
Nov 30 - Dec 1
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
Southwinds Motel

Southwinds Motel

2 out of 5
1321 Simonton Street Key West FL
$184 nightly
The price is $207 total per night
$207 total
Dec 1 - Dec 2
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
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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 $1,050, 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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