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Southernmost Point Vacation Packages

Southernmost Point Flight + Hotel Packages

Price found within the past 48 hours. Click for updated prices.
DoubleTree Resort by Hilton Grand Key - Key West

DoubleTree Resort by Hilton Grand Key - Key West

4 out of 5
Price was $1,053, price is now $834 per person
$834
per person
Jun 24 - Jun 30
found 12 hours ago
Roundtrip non-stop flight included
New Orleans (MSY) to Key West (EYW)
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 and the clean rooms in our reviews. Popular attractions Duval Street and Smathers Beach are located nearby.
The Key West Hotel

The Key West Hotel

3 out of 5
Save 100% on your flight
Price was $2,018, price is now $1,479 per person
$1,479
per person
Jun 13 - Jun 17
found 1 day ago
Roundtrip non-stop flight included
New Orleans (MSY) 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.
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 $2,768, price is now $2,121 per person
$2,121
per person
Jun 25 - Jun 30
found 14 hours ago
Roundtrip non-stop flight included
Philadelphia (PHL) 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.
Hyatt Vacation Club at Windward Pointe, Key West

Hyatt Vacation Club at Windward Pointe, Key West

3.5 out of 5
Price was $1,854, price is now $1,425 per person
$1,425
per person
Jun 3 - Jun 7
found 1 day ago
Roundtrip non-stop flight included
New Orleans (MSY) to Key West (EYW)
Stay at this hotel in Key West. Enjoy free WiFi, free parking, and a snack bar/deli. Our guests praise the pool and the helpful staff in our reviews. Popular attractions Duval Street and Smathers Beach are located nearby.
Hyatt Vacation Club at Sunset Harbor, Key West

Hyatt Vacation Club at Sunset Harbor, Key West

3.5 out of 5
Price was $1,805, price is now $1,409 per person
$1,409
per person
Jun 17 - Jun 21
found 1 day ago
Roundtrip flight included
Chicago (ORD) to Key West (EYW)
Stay at this hotel in Key West. Enjoy free WiFi, parking (surcharge), and concierge services. Popular attractions Duval Street and Mallory Square are located nearby.
The Perry Hotel & Marina Key West

The Perry Hotel & Marina Key West

4 out of 5
Price was $1,433, price is now $1,169 per person
$1,169
per person
Jun 3 - Jun 7
found 1 day ago
Roundtrip non-stop flight included
New Orleans (MSY) 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.
Duval Dream Loft by Brightwild Right on Duval

Duval Dream Loft by Brightwild Right on Duval

2 out of 5
Save 100% on your flight
Price was $4,141, price is now $3,380 per person
$3,380
per person
Jun 15 - Jun 22
found 10 hours ago
Roundtrip flight included
Chicago (ORD) to Key West (EYW)
Stay at this apartment in Key West. Popular attractions Duval Street and Ernest Hemingway Home and Museum are located nearby.
Tropical Dreaming by Avantstay 4 Blks to Beach! Private Pool!

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

3 out of 5
Save 100% on your flight
Price was $2,949, price is now $2,418 per person
$2,418
per person
Jun 13 - Jun 17
found 1 day ago
Roundtrip non-stop flight included
New Orleans (MSY) to Key West (EYW)
Stay at this cottage in Key West. Enjoy a beach locale, patios, and an in-room coffeemaker. Popular attractions Duval Street and Ernest Hemingway Home and Museum are located nearby.
Amelia Home by Avantstay In Historic Old Town w/ Pool

Amelia Home by Avantstay In Historic Old Town w/ Pool

3 out of 5
Save 100% on your flight
Price was $2,553, price is now $2,108 per person
$2,108
per person
Jun 13 - Jun 17
found 1 day ago
Roundtrip non-stop flight included
New Orleans (MSY) to Key West (EYW)
Stay at this cottage in Key West. Enjoy a beach locale, patios, and an in-room coffeemaker. Popular attractions Duval Street and Ernest Hemingway Home and Museum are located nearby.
The Cabana Inn Key West - Adults Only

The Cabana Inn Key West - Adults Only

3 out of 5
Price was $1,211, price is now $1,001 per person
$1,001
per person
Jun 24 - Jun 30
found 12 hours ago
Roundtrip non-stop flight included
New Orleans (MSY) to Key West (EYW)
Stay at this guesthouse in Key West. Enjoy free breakfast, parking (surcharge), and daily housekeeping. Our guests praise the breakfast and the pool in our reviews. Popular attractions Duval Street and Ernest Hemingway Home and Museum are located nearby.
Duval Breeze by Avantstay Great Location Close to Beach & Nightlife Shared Pool! Week Long Stays

Duval Breeze by Avantstay Great Location Close to Beach & Nightlife Shared Pool! Week Long Stays

3 out of 5
Price was $2,558, price is now $2,116 per person
$2,116
per person
Jun 18 - Jun 22
found 1 day ago
Roundtrip non-stop flight included
Philadelphia (PHL) to Key West (EYW)
Stay at this cottage in Key West. Enjoy free parking, balconies, and in-room washers/dryers. Popular attractions Duval Street and Ernest Hemingway Home and Museum are located nearby.
The Gardens Hotel

The Gardens Hotel

4 out of 5
Price was $1,720, price is now $1,424 per person
$1,424
per person
Jun 3 - Jun 7
found 1 day ago
Roundtrip non-stop flight included
New Orleans (MSY) 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.

3-4 Night Vacations in Southernmost Point

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
Price was $1,433, price is now $1,169 per person
$1,169
per person
Jun 3 - Jun 7
found 1 day ago
Roundtrip non-stop flight included
New Orleans (MSY) 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 $2,018, price is now $1,479 per person
$1,479
per person
Jun 13 - Jun 17
found 1 day ago
Roundtrip non-stop flight included
New Orleans (MSY) to Key West (EYW)
Hyatt Vacation Club at Windward Pointe, Key West

Hyatt Vacation Club at Windward Pointe, Key West

3.5 out of 5
Price was $1,854, price is now $1,425 per person
$1,425
per person
Jun 3 - Jun 7
found 1 day ago
Roundtrip non-stop flight included
New Orleans (MSY) to Key West (EYW)
Hyatt Vacation Club at Sunset Harbor, Key West

Hyatt Vacation Club at Sunset Harbor, Key West

3.5 out of 5
Old Town Key West
Price was $1,805, price is now $1,409 per person
$1,409
per person
Jun 17 - Jun 21
found 1 day ago
Roundtrip flight included
Chicago (ORD) to Key West (EYW)

5-7 Night Vacations in Southernmost Point

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

Hyatt Vacation Club at Windward Pointe, Key West

3.5 out of 5
Save 100% on your flight
Price was $2,192, price is now $1,327 per person
$1,327
per person
Jun 24 - Jun 30
found 12 hours ago
Roundtrip non-stop flight included
New Orleans (MSY) to Key West (EYW)
Southernmost House - Adult Exclusive

Southernmost House - Adult Exclusive

4 out of 5
Old Town Key West
Save 100% on your flight
Price was $2,640, price is now $1,464 per person
$1,464
per person
Jun 24 - Jun 30
found 12 hours ago
Roundtrip non-stop flight included
New Orleans (MSY) 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 $2,668, price is now $1,669 per person
$1,669
per person
Jun 24 - Jun 30
found 12 hours ago
Roundtrip non-stop flight included
New Orleans (MSY) 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 $2,219, price is now $1,422 per person
$1,422
per person
Jun 24 - Jun 30
found 12 hours ago
Roundtrip non-stop flight included
New Orleans (MSY) 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 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 ...
Southernmost Beach Resort and Guesthouses
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 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
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
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
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
Santa Maria Suites

Santa Maria Suites

4 out of 5
1401 Simonton St Key West FL
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 ...
Santa Maria Suites
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 breakfast, free WiFi, and parking (surcharge). Our guests praise the helpful staff and the property condition ...
Southernmost House - Adult Exclusive
See all 2,672 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.