Uptown - Upper Duval Vacation Packages for 2025

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Top Hotel Deals

Southernmost Beach Resort

Southernmost Beach Resort

4 out of 5
1319 Duval Street, Key West, FL
0.14 km from Uptown - Upper Duval
Stay at this 4-star beach hotel in Key West. Enjoy free WiFi, 3 outdoor pools, and a full-service spa. Our guests praise the pool and the bar in our reviews. ...
The Reach Key West, Curio Collection by Hilton

The Reach Key West, Curio Collection by Hilton

4 out of 5
1435 Simonton Street, Key West, FL
0.28 km from Uptown - Upper Duval
Stay at this 4-star beach resort in Key West. Enjoy a full-service spa, a private beach, and breakfast (surcharge). Our guests praise the helpful staff and the ...
The Southernmost Inn - Adults Only

The Southernmost Inn - Adults Only

3 out of 5
525 United Street, Key West, FL
0.04 km from Uptown - Upper Duval
Stay at this 3-star hotel in Key West. Enjoy free breakfast, 2 outdoor pools, and parking (surcharge). Our guests praise the breakfast and the pool in our reviews. ...
Southwinds Motel

Southwinds Motel

2 out of 5
1321 Simonton Street, Key West, FL
0.15 km from Uptown - Upper Duval
Stay at this hotel in Key West. Enjoy free breakfast, 2 outdoor pools, and a 24-hour front desk. Our guests praise the breakfast and the pool in our reviews. ...
Douglas House

Douglas House

3 out of 5
419 Amelia St, Key West, FL
0.19 km from Uptown - Upper Duval
Stay at this 3-star guesthouse in Key West. Enjoy free WiFi, free parking, and daily housekeeping. Popular attractions Duval Street and Ernest Hemingway Home ...
The Mansion on the Sea - Southernmost House in the USA

The Mansion on the Sea - Southernmost House in the USA

3 out of 5
1400 Duval Street, Key West, FL
0.22 km from Uptown - Upper Duval
Stay at this 3-star beach hotel in Key West. Enjoy free breakfast, room service, and parking (surcharge). Our guests praise the helpful staff and the property ...
Orchid Key Inn - Adults Only

Orchid Key Inn - Adults Only

3.5 out of 5
1004 Duval St, Key West, FL
0.34 km from Uptown - Upper Duval
Stay at this 3.5-star hotel in Key West. Enjoy free breakfast, free WiFi, and parking (surcharge). Our guests praise the breakfast and the pool in our reviews. ...
Santa Maria Suites

Santa Maria Suites

4 out of 5
1401 Simonton St, Key West, FL
0.23 km from Uptown - Upper Duval
Stay at this 4-star resort in Key West. Enjoy free WiFi, 2 outdoor pools, and a fitness center. Our guests praise the pool and the helpful staff in our reviews. ...
H2O Suites - Adults Only

H2O Suites - Adults Only

3.5 out of 5
1212 Simonton Street, Key West, FL
0.06 km from Uptown - Upper Duval
Stay at this 3.5-star business-friendly hotel in Key West. Enjoy free WiFi, a rooftop terrace, and a fitness center. Our guests praise the pool and the helpful ...
Kona Kai Oasis

Kona Kai Oasis

3 out of 5
630 South Street, Key West, FL
0.27 km from Uptown - Upper Duval
Stay at this 3-star guesthouse in Key West. Enjoy free WiFi, free parking, and a garden. Our guests praise the helpful staff in our reviews. Popular attractions ...
Oceans Edge Key West Resort, Hotel & Marina

Oceans Edge Key West Resort, Hotel & Marina

4 out of 5
5950 Peninsular Avenue, Key West, FL
7.08 km from Uptown - Upper Duval
Stay at this 4-star luxury hotel in Key West. Enjoy free WiFi, 6 outdoor pools, and a marina. Our guests praise the pool and the restaurant in our reviews. Popular ...
Margaritaville Beach House Key West

Margaritaville Beach House Key West

4 out of 5
2001 South Roosevelt Boulevard, Key West, FL
2.51 km from Uptown - Upper Duval
Stay at this 4-star beach hotel in Key West. Enjoy breakfast (surcharge), room service, and a 24-hour fitness center. Our guests praise the pool and the restaurant ...
Beachside Resort & Residences

Beachside Resort & Residences

3.5 out of 5
3841 N Roosevelt Blvd, Key West, FL
5.07 km from Uptown - Upper Duval
Stay at this 3.5-star beach hotel in Key West. Enjoy free WiFi, 2 restaurants, and a private beach. Our guests praise the pool and the helpful staff in our reviews. ...
Ibis Bay Beach Resort

Ibis Bay Beach Resort

2.5 out of 5
3101 N. Roosevelt Blvd, Key West, FL
3.51 km from Uptown - Upper Duval
Book a stay at this beach hotel in Key West. Enjoy free breakfast, free WiFi, and a private beach. Our guests praise the breakfast and the pool in our reviews. ...
The Perry Hotel & Marina Key West

The Perry Hotel & Marina Key West

4 out of 5
7001 Shrimp Road, Key West, FL
6.09 km from Uptown - Upper Duval
Stay at this 4-star business-friendly hotel in Key West. Enjoy free WiFi, 2 outdoor pools, and 2 restaurants. Our guests praise the pool and the helpful staff ...
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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.

Top Flight Deals

These prices were available within the past 7 days. Prices quoted are per person, round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

Silver Airways
Mon, May 12 - Mon, May 12
TPA
Tampa Intl.
EYW
Key West Intl.
$229 Roundtrip, found 2 days ago
$229
Roundtrip
found 2 days ago
Select Silver Airways flight, departing Mon, May 12 from Tampa Intl. to Key West Intl., returning Mon, May 12, priced at $229 found 2 days ago
Delta
Sat, Jun 7 - Wed, Jun 11
ORD
O'Hare Intl.
EYW
Key West Intl.
$323 Roundtrip, found 2 days ago
$323
Roundtrip
found 2 days ago
Select Delta flight, departing Sat, Jun 7 from O'Hare Intl. to Key West Intl., returning Wed, Jun 11, priced at $323 found 2 days ago
American Airlines
Wed, Oct 8 - Wed, Oct 15
JFK
John F. Kennedy Intl.
EYW
Key West Intl.
$329 Roundtrip, found 5 days ago
$329
Roundtrip
found 5 days ago
Select American Airlines flight, departing Wed, Oct 8 from John F. Kennedy Intl. to Key West Intl., returning Wed, Oct 15, priced at $329 found 5 days ago
Delta
Wed, Jun 25 - Tue, Jul 1
ATL
Hartsfield-Jackson Atlanta Intl.
EYW
Key West Intl.
$339 Roundtrip, found 4 days ago
$339
Roundtrip
found 4 days ago
Select Delta flight, departing Wed, Jun 25 from Hartsfield-Jackson Atlanta Intl. to Key West Intl., returning Tue, Jul 1, priced at $339 found 4 days ago