Uptown - Upper Duval Vacation Packages 2026 from $729

Uptown - Upper Duval flight + hotel vacation packages

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

Hyatt Vacation Club at Windward Pointe, Key West

Save 100% on your flight

$729

per person

Feb 27 - Mar 2

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.

The Key West Hotel

Key West Historic District

$2,628

per person

Feb 6 - Feb 13

found 2 days 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.

Oceans Edge Key West Resort, Hotel & Marina

Save 100% on your flight

$1,739

per person

Feb 11 - Feb 18

found 1 day ago

Roundtrip non-stop 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.

Hyatt Vacation Club at Beach House, Key West

Save 100% on your flight

$947

per person

Feb 26 - Mar 2

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 self parking and free WiFi. A safe deposit box and concierge services are also provided.

Southernmost Beach Resort and Guesthouses

Old Town Key West

Save 100% on your flight

$1,861

per person

Feb 6 - Feb 13

found 2 days ago

Roundtrip non-stop 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 for business? Take advantage of the 24-hour business center, laundry service, and conference space.

Top Uptown - Upper Duval hotels deals

Southernmost Beach Resort and Guesthouses

1319 Duval Street Key West FL

Free Cancellation

$402 nightly

$452 total

Jan 14 - Jan 15

Total with taxes and fees

Pool

Spa

The Reach Key West, Curio Collection by Hilton

1435 Simonton Street Key West FL

Free Cancellation

Reserve now, pay when you stay

$381 nightly

$428 total

Jan 13 - Jan 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

The Southernmost Inn - Adults Only

525 United Street Key West FL

Free Cancellation

Reserve now, pay when you stay

$309 nightly

$348 total

Jan 6 - Jan 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

Southwinds Motel

1321 Simonton Street Key West FL

$281 nightly

$316 total

Jan 5 - Jan 6

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

$306 nightly

$344 total

Jan 13 - Jan 14

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

Southernmost House

1400 Duval Street Key West FL

$450 nightly

$506 total

Jan 14 - Jan 15

Total with taxes and fees

This hotel features a restaurant, an outdoor pool, and a bar/lounge. Unwind with a drink at the poolside bar and enjoy perks like free continental breakfast and free WiFi. Self parking, a terrace, and a garden are also offered.

Pool

Breakfast included

Don't see what you're looking for?

See all available properties in Uptown - Upper Duval

View all properties

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(3,182 reviews)

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

South Beach

4/5(980 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.

Key West Butterfly and Nature Conservatory

4.5/5(760 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 $729, 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.