Uptown - Upper Duval Vacation Packages 2026 from $785

Uptown - Upper Duval flight + hotel vacation packages

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

Southernmost Beach Resort and Guesthouses

Old Town Key West

Save 100% on your flight

$785

per person

Apr 20 - Apr 23

found 2 days ago

Roundtrip flight included

Boston (BOS) to Key West (EYW)

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 Key West Hotel

Key West Historic District

Save 100% on your flight

$1,570

per person

May 21 - May 25

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

$1,511

per person

May 4 - May 10

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.

Waterfront Luxury Home - Tidelands House

Save 100% on your flight

$9,594

per person

May 24 - May 29

found 1 day ago

Roundtrip non-stop flight included

Boston (BOS) to Key West (EYW)

This vacation home doesn't skimp on freebies - guests receive free WiFi and free self parking. A garden and barbecue grills are also provided.

Oceans Edge Key West Resort, Hotel & Marina

Save 100% on your flight

$797

per person

Apr 20 - Apr 23

found 2 days ago

Roundtrip flight included

Boston (BOS) to Key West (EYW)

A marina, 6 outdoor pools, and a 24-hour gym are all featured at this smoke-free hotel. Business travelers can take advantage of the free WiFi in public areas. The restaurant provides options for dining, while the bar/lounge and poolside bar are great spots to unwind.

Top Uptown - Upper Duval hotels deals

Southernmost Beach Resort and Guesthouses

1319 Duval Street Key West FL

Free Cancellation

$577 nightly

$649 total

Mar 24 - Mar 25

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

$581 nightly

$654 total

Mar 22 - Mar 23

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

The Southernmost Inn - Adults Only

525 United Street Key West FL

Free Cancellation

Reserve now, pay when you stay

$439 nightly

$494 total

Mar 29 - Mar 30

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

Southwinds Motel

1321 Simonton Street Key West FL

$346 nightly

$390 total

Mar 29 - Mar 30

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

Douglas House

419 Amelia St Key West FL

$445 nightly

$500 total

Mar 10 - Mar 11

Total with taxes and fees

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

Pool

Free WiFi

Orchid Key Inn - Adults Only

1004 Duval St Key West FL

$583 nightly

$656 total

Mar 25 - Mar 26

Total with taxes and fees

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.

Pool

Hot Tub

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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 $785, 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.