Uptown - Upper Duval Vacation Packages 2026 from $1,198

Uptown - Upper Duval flight + hotel vacation packages

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

The Perry Hotel & Marina Key West

$1,198

per person

Aug 21 - Aug 28

found 1 day ago

Roundtrip non-stop flight included

Dallas (DAL) 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

Northside Resort

$1,231

per person

Aug 21 - Aug 28

found 1 day ago

Roundtrip non-stop flight included

Dallas (DAL) 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

Key West Historic District

Save 100% on your flight

$2,156

per person

Aug 21 - Aug 28

found 1 day ago

Roundtrip non-stop flight included

Dallas (DAL) 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 Breeze by Avantstay Great Location Close to Beach & Nightlife Shared Pool! Week Long Stays

Old Town Key West

Save 100% on your flight

$1,604

per person

Sep 14 - Sep 19

found 18 hours ago

Roundtrip non-stop flight included

Newark Liberty Intl. Airport (EWR) 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.

Beachfront 2bdr Condo, Pool & Hot Tub w/ Ocean Views Papaya Place by Avantstay

Beachside

Save 100% on your flight

$1,451

per person

Sep 8 - Sep 15

found 1 day ago

Roundtrip non-stop flight included

Indianapolis (IND) 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

$247 nightly

$278 total

Jul 6 - Jul 7

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

The Reach Key West, Curio Collection by Hilton

1435 Simonton Street Key West FL

Free Cancellation

Reserve now, pay when you stay

$228 nightly

$257 total

Jul 14 - Jul 15

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

$175 nightly

$196 total

Jul 1 - Jul 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

The Southernmost Inn - Adults Only

525 United Street Key West FL

Free Cancellation

Reserve now, pay when you stay

$152 nightly

$171 total

Jul 6 - Jul 7

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

Douglas House - Adults Only

419 Amelia St Key West FL

$105 nightly

$118 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

Santa Maria Suites

1401 Simonton St Key West FL

$399 nightly

$449 total

Jul 6 - Jul 7

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.

Popular places to visit

Southernmost Point

4.5/5(3,246 reviews)

Snap a memorable photograph from the edge of North America at this monumental landmark.

A beach with people sunbathing, palm trees, and a multi-story building in the background.

South Beach

4/5(999 reviews)

Head to the southernmost beach of the continental United States to relax and swim in the waters where famous writer Tennessee Williams once took his daily swim.

A plate with food and several butterflies.

Key West Butterfly and Nature Conservatory

4.5/5(770 reviews)

With about 60 species of butterfly, an indoor waterfall and a tropical rainforest, this nature conservatory is one of the most popular attractions in Key West.

Frequently asked questions

How much are vacation packages to Uptown - Upper Duval?

Starting from as little as $1,198, 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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With fantastic service, 24/7 customer support and some of the most perfect getaways money can buy, you'll never wander alone. And if you happen to find a lower price, we'll match it. That's our Price Match Guarantee.

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.