Uptown - Upper Duval Vacation Packages 2026 from $865

Uptown - Upper Duval flight + hotel vacation packages

Price found within the past 48 hours. Click for updated prices.

Grand Maloney Hotel

Key West Historic District

$865

per person

Dec 18 - Dec 23

found 1 day ago

Roundtrip flight included

Columbus (CMH) to Key West (EYW)

An outdoor pool is featured at this hotel, along with free WiFi in public areas and a terrace. Laundry facilities and wedding services are also provided.

The Key West Hotel

Key West Historic District

$3,897

per person

Dec 28 - Jan 2

found 1 day ago

Roundtrip non-stop flight included

Columbus (CMH) 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.

The Gardens Hotel

Old Town Key West

$1,829

per person

Jan 1 - Jan 5

found 1 day ago

Roundtrip non-stop flight included

Columbus (CMH) to Key West (EYW)

2 outdoor pools, 2 bars/lounges, and a restaurant are among this bed & breakfast's featured amenities. Business travelers can take advantage of the free WiFi in public areas. Relax with a drink at the poolside bar and enjoy the free cooked-to-order breakfast each morning.

The Perry Hotel & Marina Key West

$2,923

per person

Dec 28 - Jan 2

found 1 day ago

Roundtrip non-stop flight included

Columbus (CMH) 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.

Duval Breeze by Avantstay Great Location Close to Beach & Nightlife Shared Pool! Week Long Stays

Old Town Key West

Save 100% on your flight

$3,484

per person

Dec 31 - Jan 4

found 1 day ago

Roundtrip flight included

Chicago (ORD) to Key West (EYW)

This cottage doesn't skimp on freebies - guests receive free WiFi and free self parking. An outdoor pool is also provided.

Top Uptown - Upper Duval hotels deals

Southernmost Beach Resort and Guesthouses

1319 Duval Street Key West FL

Free Cancellation

Reserve now, pay when you stay

$279 nightly

$314 total

Nov 30 - Dec 1

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

The Southernmost Inn - Adults Only

525 United Street Key West FL

Free Cancellation

Reserve now, pay when you stay

$219 nightly

$246 total

Nov 30 - Dec 1

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

The Reach Key West, Curio Collection by Hilton

1435 Simonton Street Key West FL

Free Cancellation

Reserve now, pay when you stay

$289 nightly

$325 total

Dec 13 - Dec 14

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

Douglas House - Adults Only

419 Amelia St Key West FL

$277 nightly

$312 total

Nov 17 - Nov 18

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

Pet friendly

Southwinds Motel

1321 Simonton Street Key West FL

$184 nightly

$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

Santa Maria Suites

1401 Simonton St Key West FL

$422 nightly

$474 total

Dec 15 - Dec 16

Total with taxes and fees

This smoke-free resort features 2 outdoor pools, a gym, and a restaurant. Relax with a drink at the bar/lounge and enjoy perks like free WiFi. There's a poolside bar on site, and a 24-hour front desk and laundry facilities are also provided.

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 Uptown - Upper Duval attractions

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 Uptown - Upper Duval?

Starting from as little as $865, hotel and flight packages are an excellent way to make your travel budget stretch further. Get ready Uptown - Upper Duval — here you come!

Where can I get the best vacation package deals for Uptown - Upper Duval?

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Will I save money on my Uptown - Upper Duval car rental if I bundle it with a hotel or flight?

Combining your bookings into an Uptown - Upper Duval vacation package will save you a handsome sum. You can book a car and flight; a hotel, flight and car; or a car and hotel. You won't find a better way to explore the greater Uptown - Upper Duval area than with your own set of wheels. You can also add activities and experiences to your Travelocity package.