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Southernmost Point Vacation Packages

Southernmost Point Flight + Hotel Packages

Price found within the past 48 hours. Click for updated prices.
Hyatt Vacation Club at Beach House, Key West

Hyatt Vacation Club at Beach House, Key West

3.5 out of 5
Price was $1,306, price is now $1,027 per person
$1,027
per person
Nov 14 - Nov 18
found 1 day ago
Roundtrip non-stop flight included
Greensboro (GSO) to Key West (EYW)
Stay at this hotel in Key West. Enjoy free WiFi, parking (surcharge), and concierge services. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Duval Street and Smathers Beach are located nearby.
Casita de Catherine by Avantstay 1 Block to Duval St w/ Hot Tub!

Casita de Catherine by Avantstay 1 Block to Duval St w/ Hot Tub!

3 out of 5
Save 100% on your flight
Price was $2,814, price is now $2,035 per person
$2,035
per person
Nov 15 - Nov 22
found 13 hours ago
Roundtrip flight included
Chicago (ORD) to Key West (EYW)
Stay at this cottage in Key West. Enjoy a beach locale, patios, and in-room washers/dryers. Popular attractions Duval Street and Southernmost Point are located nearby.
Brisa Del Mar by Avantstay Communal Pool Gated Community Ocean Front

Brisa Del Mar by Avantstay Communal Pool Gated Community Ocean Front

3 out of 5
Save 100% on your flight
Price was $2,868, price is now $2,082 per person
$2,082
per person
Nov 15 - Nov 22
found 13 hours ago
Roundtrip flight included
Chicago (ORD) to Key West (EYW)
Book a stay at this beach cottage in Key West. Enjoy a beach locale, balconies, and in-room washers/dryers. Popular attractions Duval Street and Smathers Beach are located nearby.
The Key West Hotel

The Key West Hotel

3 out of 5
Price was $2,742, price is now $2,004 per person
$2,004
per person
Nov 9 - Nov 13
found 1 day ago
Roundtrip non-stop flight included
Detroit (DTW) 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.
Southernmost House - Adult Exclusive

Southernmost House - Adult Exclusive

4 out of 5
Save 100% on your flight
Price was $2,033, price is now $1,589 per person
$1,589
per person
Nov 7 - Nov 11
found 6 hours ago
Roundtrip non-stop flight included
Detroit (DTW) to Key West (EYW)
Book a stay at this beach hotel in Key West. Enjoy free WiFi, parking (surcharge), and daily housekeeping. Our guests praise the helpful staff and the property condition in our reviews. Popular attractions Duval Street and Southernmost Point are located nearby.
The Gardens Hotel

The Gardens Hotel

4 out of 5
Price was $2,301, price is now $1,821 per person
$1,821
per person
Nov 21 - Nov 25
found 1 day ago
Roundtrip flight included
Chicago (ORD) to Key West (EYW)
Book a stay at this business-friendly B&B in Key West. Enjoy free breakfast, free WiFi, and 2 outdoor pools. Our guests praise the pool and the helpful staff in our reviews. Popular attractions Duval Street and Ernest Hemingway Home and Museum are located nearby.
The Marker Key West Harbor Resort

The Marker Key West Harbor Resort

4 out of 5
Price was $2,291, price is now $1,884 per person
$1,884
per person
Nov 9 - Nov 13
found 1 day ago
Roundtrip non-stop flight included
Detroit (DTW) to Key West (EYW)
Book a stay at this business-friendly hotel in Key West. Enjoy free WiFi, 3 outdoor pools, and breakfast (surcharge). Our guests praise the pool and the helpful staff in our reviews. Popular attractions Duval Street and Mallory Square are located nearby.
Coral Villa by Avantstay Close 2 DT Key West Shared Pool & Patio!

Coral Villa by Avantstay Close 2 DT Key West Shared Pool & Patio!

3 out of 5
Price was $2,063, price is now $1,717 per person
$1,717
per person
Nov 19 - Nov 23
found 1 day ago
Roundtrip non-stop flight included
Chicago (ORD) to Key West (EYW)
Stay at this cottage in Key West. Enjoy a beach locale, balconies, and in-room washers/dryers. Popular attractions Duval Street and Smathers Beach are located nearby.
Coconut Mallory Resort And Marina By Kees Vacations

Coconut Mallory Resort And Marina By Kees Vacations

3 out of 5
Price was $1,853, price is now $1,543 per person
$1,543
per person
Nov 7 - Nov 12
found 1 day ago
Roundtrip flight included
Chicago (ORD) to Key West (EYW)
Stay at this condo in Key West. Enjoy free WiFi, free parking, and 2 outdoor pools. Our guests praise the helpful staff in our reviews. Popular attractions Duval Street and Smathers Beach are located nearby.
Amsterdam's Curry Mansion Inn

Amsterdam's Curry Mansion Inn

3 out of 5
Price was $1,651, price is now $1,376 per person
$1,376
per person
Nov 9 - Nov 13
found 1 day ago
Roundtrip non-stop flight included
Detroit (DTW) to Key West (EYW)
Book a stay at this historic guesthouse in Key West. Enjoy free WiFi, beach cabanas (surcharge), and a business center. Our guests praise the pool and the clean rooms in our reviews. Popular attractions Duval Street and Mallory Square are located nearby.
Southernmost Beach Resort and Guesthouses

Southernmost Beach Resort and Guesthouses

4 out of 5
Price was $2,029, price is now $1,691 per person
$1,691
per person
Nov 9 - Nov 13
found 1 day ago
Roundtrip non-stop flight included
Detroit (DTW) to Key West (EYW)
Book a stay at this spa 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 reviews. Popular attractions Duval Street and South Beach are located nearby.
Grand Maloney Hotel

Grand Maloney Hotel

2 out of 5
Price was $1,467, price is now $1,225 per person
$1,225
per person
Nov 7 - Nov 11
found 6 hours ago
Roundtrip non-stop flight included
Detroit (DTW) to Key West (EYW)
Stay at this hotel in Key West. Enjoy free WiFi, laundry facilities, and premium bedding. Popular attractions Duval Street and Mallory Square are located nearby.

3-4 Night Vacations in Southernmost Point

Price found within the past 48 hours. Click for updated prices.
Hyatt Vacation Club at Beach House, Key West

Hyatt Vacation Club at Beach House, Key West

3.5 out of 5
Price was $1,306, price is now $1,027 per person
$1,027
per person
Nov 14 - Nov 18
found 1 day ago
Roundtrip non-stop flight included
Greensboro (GSO) to Key West (EYW)
The Key West Hotel

The Key West Hotel

3 out of 5
Key West Historic District
Price was $2,742, price is now $2,004 per person
$2,004
per person
Nov 9 - Nov 13
found 1 day ago
Roundtrip non-stop flight included
Detroit (DTW) to Key West (EYW)
The Gardens Hotel

The Gardens Hotel

4 out of 5
Old Town Key West
Price was $2,019, price is now $1,604 per person
$1,604
per person
Nov 12 - Nov 15
found 16 hours ago
Roundtrip non-stop flight included
Greensboro (GSO) to Key West (EYW)
Sky Suites Retreat by Brightwild 2 Stunning Condos

Sky Suites Retreat by Brightwild 2 Stunning Condos

2 out of 5
Old Town Key West
Price was $6,311, price is now $5,102 per person
$5,102
per person
Nov 12 - Nov 15
found 16 hours ago
Roundtrip non-stop flight included
Greensboro (GSO) to Key West (EYW)

5-7 Night Vacations in Southernmost Point

Price found within the past 48 hours. Click for updated prices.
Amsterdam's Curry Mansion Inn

Amsterdam's Curry Mansion Inn

3 out of 5
Key West Historic District
Save 100% on your flight
Price was $1,226, price is now $875 per person
$875
per person
Nov 18 - Nov 23
found 1 day ago
Roundtrip flight included
Chicago (ORD) to Key West (EYW)
Hyatt Vacation Club at Beach House, Key West

Hyatt Vacation Club at Beach House, Key West

3.5 out of 5
Save 100% on your flight
Price was $1,568, price is now $1,090 per person
$1,090
per person
Nov 18 - Nov 23
found 1 day ago
Roundtrip flight included
Chicago (MDW) to Key West (EYW)
Eden House

Eden House

4 out of 5
Key West Historic District
Save 100% on your flight
Price was $2,608, price is now $1,860 per person
$1,860
per person
Nov 15 - Nov 22
found 13 hours ago
Roundtrip flight included
Chicago (ORD) to Key West (EYW)
The Key West Hotel

The Key West Hotel

3 out of 5
Key West Historic District
Save 100% on your flight
Price was $6,273, price is now $4,478 per person
$4,478
per person
Nov 1 - Nov 8
found 1 day ago
Roundtrip non-stop flight included
Omaha (OMA) to Key West (EYW)

Southernmost Point Last Minute Hotel Deals

Southernmost Beach Resort and Guesthouses

Southernmost Beach Resort and Guesthouses

4 out of 5
1319 Duval Street Key West FL
Book a stay at this spa 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 ...
Southernmost Beach Resort and Guesthouses
Southwinds Motel

Southwinds Motel

2 out of 5
1321 Simonton Street Key West FL
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
Casa Marina Key West, Curio Collection by Hilton

Casa Marina Key West, Curio Collection by Hilton

4 out of 5
1500 Reynolds Street Key West FL
Book a stay at this beach resort in Key West. Enjoy 2 outdoor pools, a full-service spa, and a private beach. Popular attractions Duval Street and South Beach ...
Casa Marina Key West, Curio Collection by Hilton
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
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 Reach Key West, Curio Collection by Hilton
Douglas House - Adults Only

Douglas House - Adults Only

3 out of 5
419 Amelia St Key West FL
Stay at this guesthouse in Key West. Enjoy free WiFi, daily housekeeping, and a garden. Popular attractions Duval Street and Ernest Hemingway Home and Museum ...
Douglas House - Adults Only
The Southernmost Inn - Adults Only

The Southernmost Inn - Adults Only

3 out of 5
525 United Street Key West FL
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. ...
The Southernmost Inn - Adults Only
Southernmost House - Adult Exclusive

Southernmost House - Adult Exclusive

4 out of 5
1400 Duval Street Key West FL
Book a stay at this beach hotel in Key West. Enjoy free WiFi, parking (surcharge), and daily housekeeping. Our guests praise the helpful staff and the property ...
Southernmost House - Adult Exclusive
Winslow's Bungalows - Key West Historic Inns

Winslow's Bungalows - Key West Historic Inns

4 out of 5
725 Truman Avenue Key West FL
Stay at this hotel in Key West. Enjoy free WiFi, 3 outdoor pools, and breakfast (surcharge). Our guests praise the breakfast and the pool in our reviews. Popular ...
Winslow's Bungalows - Key West Historic Inns
See all 2,598 properties in Southernmost Point
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.

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