Uptown - Upper Duval Vacation Packages 2026 from $842

Uptown - Upper Duval flight + hotel vacation packages

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

Lighthouse Hotel - Key West Historic Inns

Old Town Key West

Save 100% on your flight

$842

per person

Jul 10 - Jul 14

found 1 day ago

Roundtrip non-stop flight included

Boston (BOS) to Key West (EYW)

This hotel features an outdoor pool and a poolside bar. Guests will appreciate free perks like continental breakfast and WiFi in public areas. A terrace, a garden, and a picnic area are also on offer.

Southernmost House - Adult Exclusive

Old Town Key West

$1,708

per person

May 25 - May 31

found 1 day ago

Roundtrip non-stop flight included

Boston (BOS) to Key West (EYW)

This hotel features a restaurant, an outdoor pool, and a bar/lounge. Guests will appreciate free perks like continental breakfast and WiFi in public areas. Self parking, a terrace, and a picnic area are also offered.

The Key West Hotel

Key West Historic District

Save 100% on your flight

$1,186

per person

Jul 10 - Jul 14

found 1 day ago

Roundtrip non-stop flight included

Boston (BOS) 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.

Hyatt Vacation Club at Windward Pointe, Key West

Save 100% on your flight

$1,006

per person

Jul 10 - Jul 14

found 1 day ago

Roundtrip non-stop flight included

Boston (BOS) to Key West (EYW)

This hotel features an outdoor pool, a hot tub, and a restaurant. Guests will appreciate free perks like free self parking and WiFi in public areas. A snack bar/deli, concierge services, and barbecue grills are also on offer.

Hyatt Vacation Club at Beach House, Key West

Save 100% on your flight

$1,006

per person

Jul 10 - Jul 14

found 1 day ago

Roundtrip non-stop flight included

Boston (BOS) to Key West (EYW)

This hotel features an outdoor pool and a hot tub. Relax with a drink at the bar/lounge and enjoy perks like free WiFi. Self parking, concierge services, and barbecue grills are also on offer.

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

$330 nightly

$372 total

May 19 - May 20

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.

The Southernmost Inn - Adults Only

525 United Street Key West FL

Free Cancellation

Reserve now, pay when you stay

$264 nightly

$297 total

May 10 - May 11

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.

The Reach Key West, Curio Collection by Hilton

1435 Simonton Street Key West FL

Free Cancellation

Reserve now, pay when you stay

$326 nightly

$367 total

May 11 - May 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

1321 Simonton Street Key West FL

$252 nightly

$284 total

May 10 - May 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.

Douglas House - Adults Only

419 Amelia St Key West FL

$217 nightly

$244 total

Apr 28 - Apr 29

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.

Santa Maria Suites

1401 Simonton St Key West FL

$499 nightly

$561 total

May 10 - May 11

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.

Popular places to visit

Southernmost Point

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

South Beach

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.

Key West Butterfly and Nature Conservatory

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 $842, 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?

It's simple — look no further than Travelocity. With 400 airlines and 1,000,000 worldwide properties, it's a breeze to put together an Uptown - Upper Duval package deal that fits your budget.

Why should I purchase my Uptown - Upper Duval vacation bundle via Travelocity?

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.