Uptown - Upper Duval Vacation Packages 2026 from $764

Uptown - Upper Duval flight + hotel vacation packages

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

Winslow's Bungalows - Key West Historic Inns

Old Town Key West

$764

per person

Nov 9 - Nov 12

found 1 day ago

Roundtrip non-stop flight included

Baltimore (BWI) to Key West (EYW)

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.

Coconut Beach Resort

Old Town Key West

Save 100% on your flight

$1,552

per person

Sep 26 - Oct 3

found 1 day ago

Roundtrip non-stop flight included

Baltimore (BWI) 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.

The Key West Hotel

Key West Historic District

Save 100% on your flight

$2,394

per person

Nov 6 - Nov 10

found 1 day ago

Roundtrip non-stop flight included

Baltimore (BWI) 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.

Kona Kai Oasis

Old Town Key West

Save 100% on your flight

$1,490

per person

Oct 24 - Oct 31

found 1 day ago

Roundtrip flight included

Dallas (DFW) to Key West (EYW)

An outdoor pool, free self parking, and concierge services are featured at this guesthouse. WiFi in public areas is free. A garden, a picnic area, and luggage storage are also on offer.

The Perry Hotel & Marina Key West

Save 100% on your flight

$1,129

per person

Nov 6 - Nov 10

found 1 day ago

Roundtrip non-stop flight included

Baltimore (BWI) 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.

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

$203 nightly

$228 total

Sep 1 - Sep 2

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.

The Reach Key West, Curio Collection by Hilton

1435 Simonton Street Key West FL

Free Cancellation

Reserve now, pay when you stay

$216 nightly

$243 total

Sep 3 - Sep 4

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

1321 Simonton Street Key West FL

$155 nightly

$175 total

Aug 30 - Aug 31

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.

Douglas House - Adults Only

419 Amelia St Key West FL

$118 nightly

$133 total

Aug 26 - Aug 27

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

The Southernmost Inn - Adults Only

525 United Street Key West FL

Free Cancellation

Reserve now, pay when you stay

$138 nightly

$155 total

Aug 19 - Aug 20

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.

Santa Maria Suites

1401 Simonton St Key West FL

$339 nightly

$381 total

Aug 23 - Aug 24

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.

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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 $764, hotel and flight packages are an excellent way to make your travel budget stretch further. Get ready Uptown - Upper Duval — here you come!

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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.