Uptown - Upper Duval Vacation Packages 2026 from $921

Uptown - Upper Duval flight + hotel vacation packages

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

Hyatt Vacation Club at Beach House, Key West

$921

per person

Nov 16 - Nov 20

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.

The Key West Hotel

Key West Historic District

Save 100% on your flight

$2,017

per person

Dec 3 - Dec 6

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.

The Gardens Hotel

Old Town Key West

Save 100% on your flight

$2,127

per person

Nov 24 - Nov 30

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.

Amsterdam's Curry Mansion Inn

Key West Historic District

$1,440

per person

Nov 24 - Nov 30

found 1 day ago

Roundtrip flight included

Boston (BOS) to Key West (EYW)

This guesthouse features an outdoor pool and a bar/lounge. WiFi in public areas is free. You'll appreciate the area shuttle, business center, and coffee shop/cafe.

Tropical Dreaming by Avantstay 4 Blks to Beach! Private Pool!

Old Town Key West

Save 100% on your flight

$2,722

per person

Nov 10 - Nov 14

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.

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

$254 nightly

$286 total

Oct 6 - Oct 7

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

$159 nightly

$179 total

Oct 1 - Oct 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 Reach Key West, Curio Collection by Hilton

1435 Simonton Street Key West FL

Free Cancellation

Reserve now, pay when you stay

$259 nightly

$291 total

Oct 8 - Oct 9

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 1 - Oct 2

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

$133 nightly

$149 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.

Pool

Hot Tub

Orchid Key Inn - Adults Only

1004 Duval St Key West FL

$186 nightly

$209 total

Oct 5 - Oct 6

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.

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 $921, 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.