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Southernmost Point Vacation Packages

Southernmost Point Flight + Hotel Packages

Price found within the past 48 hours. Click for updated prices.
Winslow's Bungalows - Key West Historic Inns

Winslow's Bungalows - Key West Historic Inns

4 out of 5
Save 100% on your flight
Price was $2,032, price is now $1,358 per person
$1,358
per person
Jun 13 - Jun 20
found 1 day ago
Roundtrip non-stop flight included
Detroit (DTW) 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.
Southernmost House - Adult Exclusive

Southernmost House - Adult Exclusive

4 out of 5
Save 100% on your flight
Price was $3,201, price is now $2,053 per person
$2,053
per person
Jun 7 - Jun 14
found 1 day ago
Roundtrip non-stop flight included
Detroit (DTW) to Key West (EYW)
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 in our reviews. Popular attractions Duval Street and South Beach are located nearby.
The Key West Hotel

The Key West Hotel

3 out of 5
Save 100% on your flight
Price was $3,340, price is now $2,192 per person
$2,192
per person
Jun 13 - Jun 20
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.
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 $5,091, price is now $3,660 per person
$3,660
per person
Jun 15 - Jun 22
found 6 hours ago
Roundtrip flight included
Chicago (ORD) 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 $4,495, price is now $3,254 per person
$3,254
per person
Jun 15 - Jun 22
found 6 hours ago
Roundtrip flight included
Chicago (ORD) 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.
Southernmost Beach Resort and Guesthouses

Southernmost Beach Resort and Guesthouses

4 out of 5
Save 100% on your flight
Price was $2,059, price is now $1,495 per person
$1,495
per person
Jun 13 - Jun 20
found 1 day 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, 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.
The Marker Key West Harbor Resort

The Marker Key West Harbor Resort

4 out of 5
Save 100% on your flight
Price was $2,344, price is now $1,708 per person
$1,708
per person
Jun 13 - Jun 20
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.
Hyatt Vacation Club at Sunset Harbor, Key West

Hyatt Vacation Club at Sunset Harbor, Key West

3.5 out of 5
Save 100% on your flight
Price was $2,326, price is now $1,697 per person
$1,697
per person
Jun 25 - Jun 29
found 1 day ago
Roundtrip non-stop flight included
Detroit (DTW) 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.
Almond Tree Inn Hotel - Adults Only

Almond Tree Inn Hotel - Adults Only

3.5 out of 5
Save 100% on your flight
Price was $2,371, price is now $1,736 per person
$1,736
per person
Jun 13 - Jun 20
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 breakfast, free WiFi, and parking (surcharge). Our guests praise the breakfast and the pool in our reviews. Popular attractions Duval Street and Ernest Hemingway Home and Museum 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
Save 100% on your flight
Price was $3,415, price is now $2,525 per person
$2,525
per person
Jun 13 - Jun 20
found 1 day ago
Roundtrip non-stop flight included
Detroit (DTW) 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.
Oceans Edge Key West Resort, Hotel & Marina

Oceans Edge Key West Resort, Hotel & Marina

4 out of 5
Price was $2,052, price is now $1,546 per person
$1,546
per person
Jun 13 - Jun 20
found 1 day ago
Roundtrip non-stop flight included
Detroit (DTW) 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.
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 $2,726, price is now $2,059 per person
$2,059
per person
Jun 7 - Jun 14
found 1 day ago
Roundtrip non-stop flight included
Detroit (DTW) 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.

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 $1,458, price is now $1,119 per person
$1,119
per person
Jun 28 - Jul 2
found 1 day ago
Roundtrip non-stop flight included
Detroit (DTW) 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
Save 100% on your flight
Price was $2,326, price is now $1,697 per person
$1,697
per person
Jun 25 - Jun 29
found 1 day ago
Roundtrip non-stop flight included
Detroit (DTW) 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 $1,828, price is now $1,358 per person
$1,358
per person
Jun 25 - Jun 29
found 1 day ago
Roundtrip non-stop flight included
Detroit (DTW) 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 $2,172, price is now $1,616 per person
$1,616
per person
Jun 25 - Jun 29
found 1 day ago
Roundtrip non-stop flight included
Detroit (DTW) to Key West (EYW)

5-7 Night Vacations in Southernmost Point

Price found within the past 48 hours. Click for updated prices.
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 $2,032, price is now $1,358 per person
$1,358
per person
Jun 13 - Jun 20
found 1 day ago
Roundtrip non-stop flight included
Detroit (DTW) 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 $3,201, price is now $2,053 per person
$2,053
per person
Jun 7 - Jun 14
found 1 day ago
Roundtrip non-stop flight included
Detroit (DTW) 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 $3,340, price is now $2,192 per person
$2,192
per person
Jun 13 - Jun 20
found 1 day ago
Roundtrip non-stop flight included
Detroit (DTW) 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
Save 100% on your flight
Price was $2,460, price is now $1,632 per person
$1,632
per person
Jun 7 - Jun 13
found 21 hours ago
Roundtrip flight included
Philadelphia (PHL) 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.