Uptown - Upper Duval Vacation Packages for 2026

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Uptown - Upper Duval Flight + Hotel packages

Price found within the past 48 hours. Click for updated prices.
The Perry Hotel & Marina Key West

The Perry Hotel & Marina Key West

4 out of 5
Save 100% on your flight
Price was $1,476, price is now $1,118 per person
$1,118
per person
Mar 1 - Mar 5
found 15 hours ago
Roundtrip non-stop flight included
Providence (PVD) to Key West (EYW)
Book a stay at this business-friendly hotel in Key West. Enjoy free WiFi, 2 outdoor pools, and 2 restaurants. Our guests praise the pool and the helpful staff in our reviews. Popular attractions Duval Street and Smathers Beach are located nearby.

Oceans Edge Key West Resort, Hotel & Marina

Oceans Edge Key West Resort, Hotel & Marina

4 out of 5
Save 100% on your flight
Price was $1,729, price is now $1,148 per person
$1,148
per person
Mar 1 - Mar 5
found 15 hours ago
Roundtrip non-stop flight included
Providence (PVD) to Key West (EYW)
Book a stay at this 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 attractions Duval Street and Smathers Beach are located nearby.

The Key West Hotel

The Key West Hotel

2.5 out of 5
Key West Historic District
Save 100% on your flight
Price was $5,003, price is now $3,325 per person
$3,325
per person
Feb 14 - Feb 20
found 1 day ago
Roundtrip non-stop flight included
Cleveland (CLE) to Key West (EYW)
Stay at this guesthouse in Key West. Enjoy free WiFi, room service, and daily housekeeping. Popular attractions Duval Street and Mallory Square are located nearby.

Blue Flamingo Resort Key West

Blue Flamingo Resort Key West

4 out of 5
New Town
Save 100% on your flight
Price was $2,514, price is now $1,883 per person
$1,883
per person
Feb 14 - Feb 20
found 1 day ago
Roundtrip non-stop flight included
Cleveland (CLE) to Key West (EYW)
Book a stay at this family-friendly hotel in Key West. Enjoy free WiFi, 2 outdoor pools, and 2 restaurants. Our guests praise the pool and the helpful staff in our reviews. Popular attractions Duval Street and Smathers Beach are located nearby.

Ibis Bay Beach Resort

Ibis Bay Beach Resort

2.5 out of 5
Northside Resort
Save 100% on your flight
Price was $2,013, price is now $1,523 per person
$1,523
per person
Feb 14 - Feb 20
found 1 day ago
Roundtrip non-stop flight included
Cleveland (CLE) to Key West (EYW)
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. Popular attractions Duval Street and Smathers Beach are located nearby.

Winslow's Bungalows - Key West Historic Inns

Winslow's Bungalows - Key West Historic Inns

4 out of 5
Old Town Key West
Save 100% on your flight
Price was $2,788, price is now $2,130 per person
$2,130
per person
Feb 14 - Feb 20
found 1 day ago
Roundtrip non-stop flight included
Cleveland (CLE) to Key West (EYW)
Stay at this hotel in Key West. Enjoy free breakfast, free WiFi, and 3 outdoor pools. Our guests praise the breakfast and the pool in our reviews. Popular attractions Duval Street and Ernest Hemingway Home and Museum are located nearby.

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Top Hotel Deals

Southernmost Beach Resort and Guesthouses

Southernmost Beach Resort and Guesthouses

4 out of 5
1319 Duval Street Key West FL
0.08 km from Uptown - Upper Duval
Book a stay at this beach hotel in Key West. Enjoy free WiFi, 3 outdoor pools, and a full-service spa. Our guests praise the pool and the helpful staff in our ...
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
Book a stay at this 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 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 parking (surcharge). 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
0.2 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 ...
Southernmost House

Southernmost House

4 out of 5
1400 Duval Street Key West FL
0.22 km from Uptown - Upper Duval
Book a stay at this beach hotel in Key West. Enjoy free breakfast, free WiFi, and room service. Our guests praise the helpful staff and the property condition ...
Orchid Key Inn - Adults Only

Orchid Key Inn - Adults Only

3.5 out of 5
1004 Duval St Key West FL
0.33 km from Uptown - Upper Duval
Stay at this hotel in Key West. Enjoy free breakfast, parking (surcharge), and a 24-hour front desk. 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 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. Popular ...
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 guesthouse in Key West. Enjoy free WiFi, free parking, and a garden. Our guests praise the helpful staff in our reviews. Popular attractions Duval ...
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
Book a stay at this business-friendly hotel in Key West. Enjoy free WiFi, a rooftop terrace, and a fitness center. Our guests praise the pool and the helpful ...
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
Book a stay at this 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. ...
Blue Flamingo Resort Key West

Blue Flamingo Resort Key West

4 out of 5
3820 North Roosevelt Boulevard Key West FL
4.92 km from Uptown - Upper Duval
Book a stay at this family-friendly hotel in Key West. Enjoy free WiFi, 2 outdoor pools, and 2 restaurants. Our guests praise the pool and the helpful staff ...
Oceans Edge Key West Resort, Hotel & Marina

Oceans Edge Key West Resort, Hotel & Marina

4 out of 5
5950 Peninsular Avenue Key West FL
7.05 km from Uptown - Upper Duval
Book a stay at this 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
Book a stay at this beach hotel in Key West. Enjoy breakfast (surcharge), room service, and a 24-hour fitness center. Our guests praise the pool and the restaurant ...
DoubleTree Resort by Hilton Grand Key - Key West

DoubleTree Resort by Hilton Grand Key - Key West

4 out of 5
3990 S Roosevelt Blvd Key West FL
4.86 km from Uptown - Upper Duval
Book a stay at this business-friendly resort in Key West. Enjoy free WiFi, breakfast (surcharge), and a free airport shuttle. Our guests praise 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.

Breeze Airways
Thu, Jan 29 - Mon, Feb 2
TPA
Tampa Intl.
EYW
Key West Intl.
$110 Roundtrip, found 9 hours ago
$110
Roundtrip
found 9 hours ago
Select Breeze Airways flight, departing Thu, Jan 29 from Tampa Intl. to Key West Intl., returning Mon, Feb 2, priced at $110 found 9 hours ago
Delta
Mon, Jan 26 - Fri, Jan 30
BOS
Logan Intl.
EYW
Key West Intl.
$227 Roundtrip, found 3 days ago
$227
Roundtrip
found 3 days ago
Select Delta flight, departing Mon, Jan 26 from Logan Intl. to Key West Intl., returning Fri, Jan 30, priced at $227 found 3 days ago
JetBlue Airways
Mon, Mar 2 - Thu, Mar 19
PHL
Philadelphia Intl.
EYW
Key West Intl.
$284 Roundtrip, found 3 days ago
$284
Roundtrip
found 3 days ago
Select JetBlue Airways flight, departing Mon, Mar 2 from Philadelphia Intl. to Key West Intl., returning Thu, Mar 19, priced at $284 found 3 days ago
United
Sat, Jan 24 - Fri, Jan 30
BOS
Logan Intl.
EYW
Key West Intl.
$297 Roundtrip, found 3 days ago
$297
Roundtrip
found 3 days ago
Select United flight, departing Sat, Jan 24 from Logan Intl. to Key West Intl., returning Fri, Jan 30, priced at $297 found 3 days ago
American Airlines
Wed, Mar 11 - Tue, Mar 17
BOS
Logan Intl.
EYW
Key West Intl.
$319 Roundtrip, found 2 days ago
$319
Roundtrip
found 2 days ago
Select American Airlines flight, departing Wed, Mar 11 from Logan Intl. to Key West Intl., returning Tue, Mar 17, priced at $319 found 2 days ago