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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 $1,826, price is now $1,021 per person
$1,021
per person
Feb 1 - Feb 6
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) 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.
Southernmost House

Southernmost House

4 out of 5
Price was $3,053, price is now $2,049 per person
$2,049
per person
Jan 22 - Jan 27
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Key West (EYW)
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 in our reviews. Popular attractions Duval Street and Southernmost Point are located nearby.
The Key West Hotel

The Key West Hotel

2.5 out of 5
Price was $3,392, price is now $2,288 per person
$2,288
per person
Jan 22 - Jan 27
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) 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.
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 $2,830, price is now $2,020 per person
$2,020
per person
Jan 28 - Feb 3
found 1 day ago
Roundtrip flight included
Washington (DCA) to Key West (EYW)
Stay at this cottage in Key West. Enjoy balconies, in-room washers/dryers, and an in-room coffeemaker. 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 $1,591, price is now $1,138 per person
$1,138
per person
Feb 5 - Feb 9
found 1 hour ago
Roundtrip flight included
Washington (WAS) 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.
Winslow's Bungalows - Key West Historic Inns

Winslow's Bungalows - Key West Historic Inns

4 out of 5
Price was $1,990, price is now $1,427 per person
$1,427
per person
Jan 22 - Jan 27
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) 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.
Lighthouse Hotel - Key West Historic Inns

Lighthouse Hotel - Key West Historic Inns

3.5 out of 5
Price was $1,952, price is now $1,402 per person
$1,402
per person
Jan 22 - Jan 27
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Key West (EYW)
Stay at this hotel in Key West. Enjoy free breakfast, free WiFi, and daily housekeeping. Our guests praise the helpful staff in our reviews. 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 $2,184, price is now $1,598 per person
$1,598
per person
Feb 4 - Feb 10
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) 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.
New Waterfront Home - Dreamside House

New Waterfront Home - Dreamside House

2 out of 5
Save 100% on your flight
Price was $13,778, price is now $10,482 per person
$10,482
per person
Jan 24 - Jan 31
found 1 day ago
Roundtrip flight included
Boston (BOS) to Key West (EYW)
Stay at this vacation home in Key West. Enjoy free parking and a garden. 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 $1,654, price is now $1,258 per person
$1,258
per person
Feb 3 - Feb 7
found 1 day ago
Roundtrip flight included
Washington (DCA) 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
Price was $1,667, price is now $1,271 per person
$1,271
per person
Jan 22 - Jan 27
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) 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.
Oceans Edge Key West Resort, Hotel & Marina

Oceans Edge Key West Resort, Hotel & Marina

4 out of 5
Price was $1,628, price is now $1,245 per person
$1,245
per person
Jan 22 - Jan 27
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) 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.

3-4 Night Vacations in South Beach

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 $935, price is now $513 per person
$513
per person
Jan 19 - Jan 22
found 1 day ago
Roundtrip flight included
Boston (BOS) 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 $1,889, price is now $1,023 per person
$1,023
per person
Jan 19 - Jan 22
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) 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 $952, price is now $522 per person
$522
per person
Jan 19 - Jan 22
found 1 day ago
Roundtrip flight included
Boston (BOS) to Key West (EYW)
Ella's Cottages - Key West Historic Inns

Ella's Cottages - Key West Historic Inns

3.5 out of 5
Old Town Key West
Save 100% on your flight
Price was $1,255, price is now $724 per person
$724
per person
Jan 19 - Jan 22
found 1 day ago
Roundtrip flight included
Boston (BOS) to Key West (EYW)

5-7 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 $1,826, price is now $1,021 per person
$1,021
per person
Feb 1 - Feb 6
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Key West (EYW)
Southernmost House

Southernmost House

4 out of 5
Old Town Key West
Price was $3,053, price is now $2,049 per person
$2,049
per person
Jan 22 - Jan 27
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Key West (EYW)
The Key West Hotel

The Key West Hotel

2.5 out of 5
Key West Historic District
Price was $3,392, price is now $2,288 per person
$2,288
per person
Jan 22 - Jan 27
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) 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 $2,830, price is now $2,020 per person
$2,020
per person
Jan 28 - Feb 3
found 1 day ago
Roundtrip flight included
Washington (DCA) 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
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
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
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
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
Kona Kai Oasis

Kona Kai Oasis

3 out of 5
630 South Street Key West FL
Stay at this guesthouse in Key West. Enjoy free WiFi, free parking, and a garden. Our guests praise the helpful staff in our reviews. Popular attractions Duval ...
Kona Kai Oasis
See all 2,752 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.