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South Beach Vacation Packages

South Beach Flight + Hotel Packages

Price found within the past 48 hours. Click for updated prices.
Oceans Edge Key West Resort, Hotel & Marina

Oceans Edge Key West Resort, Hotel & Marina

4 out of 5
Price was $806, price is now $632 per person
$632
per person
Sep 29 - Oct 3
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Key West (EYW)
Stay at this 4-star 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 Beach House, Key West

Hyatt Vacation Club at Beach House, Key West

3.5 out of 5
Price was $1,490, price is now $1,165 per person
$1,165
per person
Oct 18 - Oct 22
found 2 hours ago
Roundtrip non-stop flight included
Philadelphia (PHL) to Key West (EYW)
Stay at this 3.5-star eco-certified 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.
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 $3,328, price is now $2,475 per person
$2,475
per person
Sep 30 - Oct 7
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Key West (EYW)
Stay at this 3-star 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.
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 $1,248, price is now $952 per person
$952
per person
Oct 20 - Oct 24
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Key West (EYW)
Stay at this 3.5-star eco-certified 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.
Southernmost Beach Resort and Guesthouses

Southernmost Beach Resort and Guesthouses

4 out of 5
Price was $939, price is now $720 per person
$720
per person
Sep 29 - Oct 3
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Key West (EYW)
Stay at this 4-star beach hotel in Key West. Enjoy free WiFi, 3 outdoor pools, and a full-service spa. Our guests praise the pool and the bar in our reviews. Popular attractions Duval Street and South Beach are located nearby.
Conch Adventure by Avantstay Great Location w/ Patio, Outdoor Dining and Shared Pool! Week Long Stays

Conch Adventure by Avantstay Great Location w/ Patio, Outdoor Dining and Shared Pool! Week Long Stays

3 out of 5
Save 100% on your flight
Price was $1,919, price is now $1,491 per person
$1,491
per person
Sep 30 - Oct 7
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Key West (EYW)
Stay at this 3-star cottage in Key West. Enjoy a beach locale, patios, and in-room washers/dryers. Popular attractions Duval Street and Ernest Hemingway Home and Museum are located nearby.
Almond Tree Inn Hotel - Adults Only

Almond Tree Inn Hotel - Adults Only

3.5 out of 5
Price was $1,257, price is now $976 per person
$976
per person
Sep 29 - Oct 3
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Key West (EYW)
Stay at this 3.5-star 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.
Orchid Key Inn - Adults Only

Orchid Key Inn - Adults Only

3.5 out of 5
Price was $1,254, price is now $976 per person
$976
per person
Sep 29 - Oct 3
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Key West (EYW)
Stay at this 3.5-star 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.
Always Your Paradise by Avantstay Shared Pool Near Zachary Beach! Week Long Stays Only

Always Your Paradise by Avantstay Shared Pool Near Zachary Beach! Week Long Stays Only

3 out of 5
Save 100% on your flight
Price was $1,822, price is now $1,432 per person
$1,432
per person
Sep 30 - Oct 7
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Key West (EYW)
Stay at this 3-star cottage in Key West. Enjoy free parking, concierge services, and patios. Popular attractions Duval Street and Ernest Hemingway Home and Museum are located nearby.
Bahamian Reed by Avantstay Walk to Everything! w/ Community Pool Week Long Stays Only

Bahamian Reed by Avantstay Walk to Everything! w/ Community Pool Week Long Stays Only

3 out of 5
Save 100% on your flight
Price was $2,012, price is now $1,581 per person
$1,581
per person
Sep 30 - Oct 7
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Key West (EYW)
Stay at this 3-star cottage in Key West. Enjoy balconies, in-room washers/dryers, and an in-room coffeemaker. Popular attractions Duval Street and Ernest Hemingway Home and Museum are located nearby.
Havana Cabana at Key West

Havana Cabana at Key West

4 out of 5
Price was $933, price is now $734 per person
$734
per person
Oct 6 - Oct 10
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Key West (EYW)
Stay at this 4-star business-friendly hotel in Key West. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the pool and the bar in our reviews. Popular attractions Duval Street and Smathers Beach are located nearby.
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 $2,214, price is now $1,760 per person
$1,760
per person
Oct 2 - Oct 10
just found
Roundtrip non-stop flight included
Boston (BOS) to Key West (EYW)
Stay at this 4-star villa in Key West. Enjoy free parking, a beach locale, and a garden. Popular attractions Duval Street and Smathers Beach are located nearby.

3-4 Night Vacations in South Beach

Price found within the past 48 hours. Click for updated prices.
Southernmost Beach Resort and Guesthouses

Southernmost Beach Resort and Guesthouses

4 out of 5
Old Town Key West
Price was $939, price is now $720 per person
$720
per person
Sep 29 - Oct 3
found 1 day ago
Roundtrip flight included
Atlanta (ATL) 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
Price was $1,263, price is now $930 per person
$930
per person
Oct 19 - Oct 22
found 1 day ago
Roundtrip flight included
Philadelphia (PHL) 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
Save 100% on your flight
Price was $1,248, price is now $952 per person
$952
per person
Oct 20 - Oct 24
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Key West (EYW)
Almond Tree Inn Hotel - Adults Only

Almond Tree Inn Hotel - Adults Only

3.5 out of 5
Old Town Key West
Price was $1,257, price is now $976 per person
$976
per person
Sep 29 - Oct 3
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Key West (EYW)

5-7 Night Vacations in South Beach

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 $796, price is now $545 per person
$545
per person
Sep 29 - Oct 4
found 1 day ago
Roundtrip flight included
Atlanta (ATL) 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
Save 100% on your flight
Price was $1,516, price is now $912 per person
$912
per person
Oct 18 - Oct 23
found 12 hours ago
Roundtrip non-stop flight included
Boston (BOS) to Key West (EYW)
Oceans Edge Key West Resort, Hotel & Marina

Oceans Edge Key West Resort, Hotel & Marina

4 out of 5
Price was $819, price is now $567 per person
$567
per person
Sep 29 - Oct 4
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Key West (EYW)
Pier House Resort & Spa

Pier House Resort & Spa

4 out of 5
Key West Historic District
Save 100% on your flight
Price was $1,392, price is now $969 per person
$969
per person
Sep 29 - Oct 4
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Key West (EYW)

South Beach Last Minute Hotel Deals

Southernmost Beach Resort and Guesthouses

Southernmost Beach Resort and Guesthouses

4 out of 5
1319 Duval Street, Key West, FL
Stay at this 4-star beach hotel in Key West. Enjoy free WiFi, 3 outdoor pools, and a full-service spa. Our guests praise the pool and the bar in our reviews. ...
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
Stay at this 4-star 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
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
Stay at this 4-star 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 3-star 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 a 24-hour front desk. Our guests praise the breakfast and the pool in our reviews. ...
Southwinds Motel
Santa Maria Suites

Santa Maria Suites

4 out of 5
1401 Simonton St, Key West, FL
Stay at this 4-star 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. ...
Santa Maria Suites
Southernmost House

Southernmost House

4 out of 5
1400 Duval Street, Key West, FL
Stay at this 4-star 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
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 4-star 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 ...
Winslow's Bungalows - Key West Historic Inns
See all 2,682 properties in South Beach
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.