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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 $1,891, price is now $1,435 per person
$1,435
per person
Mar 23 - Mar 27
found 1 day ago
Roundtrip non-stop flight included
St. Louis (STL) to Key West (EYW)
Stay at this hotel in Key West. Enjoy free WiFi, free parking, 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.
The Key West Hotel

The Key West Hotel

2.5 out of 5
Save 100% on your flight
Price was $2,907, price is now $1,807 per person
$1,807
per person
Mar 16 - Mar 20
found 1 day ago
Roundtrip non-stop flight included
Hartford (BDL) 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.
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 $2,647, price is now $1,753 per person
$1,753
per person
Mar 9 - Mar 16
found 1 day ago
Roundtrip non-stop flight included
Hartford (BDL) 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.
Ibis Bay Beach Resort

Ibis Bay Beach Resort

2.5 out of 5
Save 100% on your flight
Price was $2,084, price is now $1,496 per person
$1,496
per person
Mar 9 - Mar 16
found 1 day ago
Roundtrip non-stop flight included
Hartford (BDL) 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.
Blue Flamingo Resort Key West

Blue Flamingo Resort Key West

4 out of 5
Save 100% on your flight
Price was $2,205, price is now $1,588 per person
$1,588
per person
Mar 9 - Mar 16
found 1 day ago
Roundtrip non-stop flight included
Hartford (BDL) 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.
Southernmost Beach Resort and Guesthouses

Southernmost Beach Resort and Guesthouses

4 out of 5
Save 100% on your flight
Price was $3,195, price is now $2,339 per person
$2,339
per person
Mar 9 - Mar 16
found 1 day ago
Roundtrip non-stop flight included
Hartford (BDL) 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 Southernmost Point are located nearby.
Pier House Resort & Spa

Pier House Resort & Spa

4 out of 5
Save 100% on your flight
Price was $3,689, price is now $2,717 per person
$2,717
per person
Mar 9 - Mar 16
found 1 day ago
Roundtrip non-stop flight included
Hartford (BDL) to Key West (EYW)
Book a stay at this beach resort in Key West. Enjoy a full-service spa, a private beach, and 2 bars/lounges. Our guests praise the pool and the helpful staff in our reviews. Popular attractions Duval Street and Mallory Square are located nearby.
Tranquility by Avantstay Close to Duval St w/ BBQ & Shared Pool

Tranquility by Avantstay Close to Duval St w/ BBQ & Shared Pool

3 out of 5
Save 100% on your flight
Price was $5,468, price is now $4,043 per person
$4,043
per person
Mar 6 - Mar 14
found 5 hours ago
Roundtrip flight included
Chicago (ORD) to Key West (EYW)
Stay at this cottage in Key West. Enjoy patios, in-room washers/dryers, and an in-room coffeemaker. Popular attractions Duval Street and Ernest Hemingway Home and Museum are located nearby.
The Perry Hotel & Marina Key West

The Perry Hotel & Marina Key West

4 out of 5
Save 100% on your flight
Price was $2,540, price is now $1,894 per person
$1,894
per person
Mar 9 - Mar 16
found 1 day ago
Roundtrip non-stop flight included
Hartford (BDL) 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.
Havana Cabana at Key West

Havana Cabana at Key West

4 out of 5
Save 100% on your flight
Price was $2,307, price is now $1,747 per person
$1,747
per person
Mar 9 - Mar 16
found 1 day ago
Roundtrip non-stop flight included
Hartford (BDL) to Key West (EYW)
Book a stay at this business-friendly hotel in Key West. Enjoy free WiFi, free parking, and breakfast (surcharge). 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 Windward Pointe, Key West

Hyatt Vacation Club at Windward Pointe, Key West

3.5 out of 5
Save 100% on your flight
Price was $2,614, price is now $1,983 per person
$1,983
per person
Mar 21 - Mar 28
found 3 hours ago
Roundtrip flight included
Hartford (BDL) 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.
The Reach Key West, Curio Collection by Hilton

The Reach Key West, Curio Collection by Hilton

4 out of 5
Save 100% on your flight
Price was $3,459, price is now $2,650 per person
$2,650
per person
Mar 9 - Mar 16
found 1 day ago
Roundtrip non-stop flight included
Hartford (BDL) to Key West (EYW)
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 property condition in our reviews. Popular attractions Duval Street and Southernmost Point are located nearby.

3-4 Night Vacations in Southernmost Point

Price found within the past 48 hours. Click for updated prices.
Paradise Place by Avantstay Key West Old Town Condo w/ Shared Pool

Paradise Place by Avantstay Key West Old Town Condo w/ Shared Pool

3 out of 5
Key West Historic District
Save 100% on your flight
Price was $1,623, price is now $1,329 per person
$1,329
per person
Mar 2 - Mar 6
found 1 day ago
Roundtrip non-stop flight included
Chicago (ORD) to Key West (EYW)
Coral Garden by Avantstay Great Location w/ Balcony & Shared Pool

Coral Garden by Avantstay Great Location w/ Balcony & Shared Pool

4 out of 5
Save 100% on your flight
Price was $2,345, price is now $1,871 per person
$1,871
per person
Mar 13 - Mar 16
found 24 hours ago
Roundtrip non-stop flight included
Philadelphia (PHL) to Key West (EYW)
Coral Palm by Avantstay Key West Walkable Gated Community & Shared Pool

Coral Palm by Avantstay Key West Walkable Gated Community & Shared Pool

3 out of 5
Save 100% on your flight
Price was $2,616, price is now $2,105 per person
$2,105
per person
Feb 27 - Mar 3
found 24 hours ago
Roundtrip non-stop flight included
Hartford (BDL) to Key West (EYW)
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
Old Town Key West
Save 100% on your flight
Price was $4,390, price is now $3,539 per person
$3,539
per person
Mar 13 - Mar 17
found 1 day ago
Roundtrip non-stop 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.
Ibis Bay Beach Resort

Ibis Bay Beach Resort

2.5 out of 5
Northside Resort
Save 100% on your flight
Price was $2,084, price is now $1,496 per person
$1,496
per person
Mar 9 - Mar 16
found 1 day ago
Roundtrip non-stop flight included
Hartford (BDL) to Key West (EYW)
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 $2,647, price is now $1,753 per person
$1,753
per person
Mar 9 - Mar 16
found 1 day ago
Roundtrip non-stop flight included
Hartford (BDL) to Key West (EYW)
The Key West Hotel

The Key West Hotel

2.5 out of 5
Key West Historic District
Save 100% on your flight
Price was $3,817, price is now $2,574 per person
$2,574
per person
Mar 12 - Mar 17
found 1 day ago
Roundtrip non-stop flight included
Hartford (BDL) to Key West (EYW)
Blue Flamingo Resort Key West

Blue Flamingo Resort Key West

4 out of 5
New Town
Save 100% on your flight
Price was $2,205, price is now $1,588 per person
$1,588
per person
Mar 9 - Mar 16
found 1 day ago
Roundtrip non-stop flight included
Hartford (BDL) 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
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
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
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
Southernmost House

Southernmost House

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 room service. Our guests praise the helpful staff and the property condition ...
Southernmost House
Douglas House

Douglas House

3 out of 5
419 Amelia St Key West FL
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 ...
Douglas House
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 breakfast, free WiFi, and 3 outdoor pools. Our guests praise the breakfast and the pool in our reviews. Popular attractions ...
Winslow's Bungalows - Key West Historic Inns
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 Southernmost ...
Casa Marina Key West, Curio Collection by Hilton
See all 2,745 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.