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South Beach Vacation Packages

South Beach 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
Save 100% on your flight
Price was $958, price is now $615 per person
$615
per person
Oct 26 - Oct 30
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 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 Perry Hotel & Marina Key West

The Perry Hotel & Marina Key West

4 out of 5
Save 100% on your flight
Price was $1,053, price is now $712 per person
$712
per person
Oct 29 - Nov 2
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, 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.
Oceans Edge Key West Resort, Hotel & Marina

Oceans Edge Key West Resort, Hotel & Marina

4 out of 5
Price was $926, price is now $656 per person
$656
per person
Oct 29 - Nov 2
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.
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 $5,138, price is now $3,722 per person
$3,722
per person
Nov 3 - Nov 8
found 1 day ago
Roundtrip flight included
Boston (BOS) to Key West (EYW)
Stay at this 3-star cottage in Key West. Enjoy patios, an in-room coffeemaker, and air conditioning. Popular attractions Duval Street and Ernest Hemingway Home and Museum are located nearby.
Pier House Resort & Spa

Pier House Resort & Spa

4 out of 5
Save 100% on your flight
Price was $1,505, price is now $1,100 per person
$1,100
per person
Oct 29 - Nov 2
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Key West (EYW)
Stay at this 4-star beach resort in Key West. Enjoy a full-service spa, a private beach, and 2 bars/lounges. Our guests praise the pool and the bar in our reviews. Popular attractions Duval Street and Mallory Square are located nearby.
Duval Sea Turtle by Avantstay Great Location Close to Shops Shared Pool!

Duval Sea Turtle by Avantstay Great Location Close to Shops Shared Pool!

3.5 out of 5
Save 100% on your flight
Price was $3,683, price is now $2,701 per person
$2,701
per person
Nov 3 - Nov 8
found 1 day ago
Roundtrip flight included
Boston (BOS) to Key West (EYW)
Stay at this 3.5-star cottage in Key West. Enjoy free parking, concierge services, and premium TV channels. Popular attractions Duval Street and Ernest Hemingway Home and Museum are located nearby.
Ibis Bay Beach Resort

Ibis Bay Beach Resort

2.5 out of 5
Price was $912, price is now $683 per person
$683
per person
Oct 29 - Nov 2
found 1 day ago
Roundtrip flight included
Atlanta (ATL) 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.
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 $2,351, price is now $1,762 per person
$1,762
per person
Nov 3 - Nov 8
found 1 day ago
Roundtrip flight included
Boston (BOS) to Key West (EYW)
Stay at this 3-star 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.
Southernmost Beach Resort and Guesthouses

Southernmost Beach Resort and Guesthouses

4 out of 5
Price was $1,003, price is now $754 per person
$754
per person
Oct 29 - Nov 2
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.
Lighthouse Hotel - Key West Historic Inns

Lighthouse Hotel - Key West Historic Inns

3.5 out of 5
Save 100% on your flight
Price was $1,222, price is now $921 per person
$921
per person
Oct 29 - Nov 2
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 daily housekeeping. Our guests praise the helpful staff and the property condition in our reviews. Popular attractions Duval Street and Ernest Hemingway Home and Museum are located nearby.
The Grand Guesthouse

The Grand Guesthouse

2.5 out of 5
Price was $1,571, price is now $1,191 per person
$1,191
per person
Oct 30 - Nov 3
found 18 hours ago
Roundtrip flight included
Atlanta (ATL) to Key West (EYW)
Stay at this guesthouse in Key West. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff in our reviews. Popular attractions Duval Street and South 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 $1,047, price is now $806 per person
$806
per person
Oct 28 - Nov 1
found 15 hours ago
Roundtrip flight included
Atlanta (ATL) 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.

3-4 Night Vacations in South Beach

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
Save 100% on your flight
Price was $752, price is now $446 per person
$446
per person
Nov 14 - Nov 17
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 $764, price is now $460 per person
$460
per person
Nov 14 - Nov 17
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Key West (EYW)
The Perry Hotel & Marina Key West

The Perry Hotel & Marina Key West

4 out of 5
Save 100% on your flight
Price was $1,053, price is now $712 per person
$712
per person
Oct 29 - Nov 2
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Key West (EYW)
Oceans Edge Key West Resort, Hotel & Marina

Oceans Edge Key West Resort, Hotel & Marina

4 out of 5
Price was $926, price is now $656 per person
$656
per person
Oct 29 - Nov 2
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.
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 $1,499, price is now $907 per person
$907
per person
Oct 31 - Nov 7
found 1 day ago
Roundtrip flight included
Boston (BOS) to Key West (EYW)
The Perry Hotel & Marina Key West

The Perry Hotel & Marina Key West

4 out of 5
Save 100% on your flight
Price was $1,732, price is now $1,114 per person
$1,114
per person
Oct 31 - Nov 7
found 1 day ago
Roundtrip flight included
Boston (BOS) to Key West (EYW)
Ridley House - Key West Historic Inns

Ridley House - Key West Historic Inns

3.5 out of 5
Key West Historic District
Save 100% on your flight
Price was $3,783, price is now $2,461 per person
$2,461
per person
Oct 22 - Oct 28
found 23 hours ago
Roundtrip flight included
Boston (BOS) 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 $1,607, price is now $1,051 per person
$1,051
per person
Nov 9 - Nov 15
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) 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
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 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
Margaritaville Beach House Key West

Margaritaville Beach House Key West

4 out of 5
2001 South Roosevelt Boulevard, Key West, FL
Stay at this 4-star beach hotel in Key West. Enjoy breakfast (surcharge), room service, and a 24-hour fitness center. Our guests praise the pool and the restaurant ...
Margaritaville Beach House Key West
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
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
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
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 2,706 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.