Uptown - Upper Duval Vacation Packages 2026 from $2,500

Uptown - Upper Duval flight + hotel vacation packages

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

Hyatt Vacation Club at Sunset Harbor, Key West

Old Town Key West

$2,500

per person

Dec 21 - Dec 27

found 1 day ago

Roundtrip flight included

Boston (BOS) to Key West (EYW)

An outdoor pool, self parking, and concierge services are featured at this hotel. WiFi in public areas is free.

The Key West Hotel

Key West Historic District

$2,990

per person

Nov 5 - Nov 10

found 1 day ago

Roundtrip 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.

Amelia Home by Avantstay In Historic Old Town w/ Pool

Old Town Key West

Save 100% on your flight

$2,561

per person

Nov 19 - Nov 24

found 1 day ago

Roundtrip non-stop flight included

Boston (BOS) to Key West (EYW)

An outdoor pool is featured at this cottage, along with free WiFi in public areas and barbecue grills.

The Gardens Hotel

Old Town Key West

$3,298

per person

Dec 17 - Dec 23

found 1 day ago

Roundtrip flight included

Boston (BOS) to Key West (EYW)

2 outdoor pools, 2 bars/lounges, and a restaurant are among this bed & breakfast's featured amenities. Business travelers can take advantage of the free WiFi in public areas. Relax with a drink at the poolside bar and enjoy the free cooked-to-order breakfast each morning.

New Crestwood House by Brightwild Huge Pool

Save 100% on your flight

$15,094

per person

Dec 27 - Jan 1

found 1 day ago

Roundtrip flight included

Newark Liberty Intl. Airport (EWR) to Key West (EYW)

A gym, free self parking, and barbecue grills are featured at this vacation home. WiFi in public areas is free. A garden 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

$243 nightly

$274 total

Oct 11 - Oct 12

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, free WiFi in public areas, and laundry service. 2 poolside bars and 2 bars/lounges are featured at this hotel, along with a gym.

Pool

Spa

Southwinds Motel

1321 Simonton Street Key West FL

$169 nightly

$190 total

Oct 5 - Oct 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

The Reach Key West, Curio Collection by Hilton

1435 Simonton Street Key West FL

Free Cancellation

Reserve now, pay when you stay

$276 nightly

$310 total

Oct 14 - Oct 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

Douglas House - Adults Only

419 Amelia St Key West FL

$169 nightly

$190 total

Oct 5 - Oct 6

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

$141 nightly

$159 total

Oct 5 - Oct 6

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.

H2O Suites - Adults Only

1212 Simonton Street Key West FL

$369 nightly

$415 total

Oct 4 - Oct 5

Total with taxes and fees

This hotel features a bar/lounge, a poolside bar, and an outdoor pool. Business travelers can take advantage of the laundry service. There's a gym on site, and a 24-hour front desk and a rooftop terrace 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 $2,500, 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?

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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.