South Beach Flight + Hotel Packages

Price found within the past 48 hours. Click for updated prices.

24 North Hotel Key West - Newly Renovated

per person

Feb 21 - Feb 25

found 1 day ago

Roundtrip flight included

Boston (BOS) to Key West (EYW)

Stay at this 4-star eco-certified hotel in Key West. Enjoy free WiFi, 2 restaurants, and 2 bars/lounges. Our guests praise the pool and the helpful staff in our reviews. Popular attractions Smathers Beach and Duval Street are located nearby.

Oceans Edge Key West Resort, Hotel & Marina

Save 100% on your flight

per person

Feb 21 - Feb 25

found 1 day ago

Roundtrip flight included

Boston (BOS) to Key West (EYW)

Stay at this 4-star golf 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 Smathers Beach and Southernmost Point are located nearby.

Ella's Cottages - Key West Historic Inns

Save 100% on your flight

per person

Feb 21 - Feb 25

found 1 day ago

Roundtrip flight included

Boston (BOS) 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 helpful staff in our reviews. Popular attractions Duval Street and Ernest Hemingway Home and Museum are located nearby.

Paradise Inn Key West - Adults Only

Save 100% on your flight

per person

Feb 21 - Feb 25

found 1 day ago

Roundtrip flight included

Boston (BOS) to Key West (EYW)

Stay at this 3.5-star hotel in Key West. Enjoy parking (surcharge), daily housekeeping, and a garden. Our guests praise the breakfast and the pool in our reviews. Popular attractions Ernest Hemingway Home and Museum and Duval Street are located nearby.

Ibis Bay Beach Resort

per person

Feb 21 - Feb 25

found 1 day ago

Roundtrip flight included

Boston (BOS) 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 Smathers Beach and Duval Street are located nearby.

The Gates Hotel Key West Newly Renovated

per person

Feb 21 - Feb 25

found 1 day ago

Roundtrip flight included

Boston (BOS) to Key West (EYW)

Stay at this 4-star eco-certified hotel in Key West. Enjoy free WiFi, 2 restaurants, and breakfast (surcharge). Our guests praise the pool and the helpful staff in our reviews. Popular attractions Smathers Beach and Duval Street are located nearby.

Douglas House

Save 100% on your flight

per person

Mar 17 - Mar 21

found 1 day ago

Roundtrip flight included

Boston (BOS) to Key West (EYW)

Stay at this 3-star guesthouse in Key West. Enjoy free WiFi, free parking, and daily housekeeping. Popular attractions Ernest Hemingway Home and Museum and Southernmost Point are located nearby.

The Southernmost Inn - Adults Only

Save 100% on your flight

per person

Feb 21 - Feb 25

found 1 day ago

Roundtrip flight included

Boston (BOS) to Key West (EYW)

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. Popular attractions Southernmost Point and Ernest Hemingway Home and Museum are located nearby.

Margaritaville Beach House Key West

Save 100% on your flight

per person

Feb 21 - Feb 25

found 1 day ago

Roundtrip flight included

Boston (BOS) to Key West (EYW)

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 in our reviews. Popular attractions Smathers Beach and Southernmost Point are located nearby.

Havana Cabana at Key West - Adults Only

Save 100% on your flight

per person

Feb 24 - Mar 4

found 1 day ago

Roundtrip flight included

Boston (BOS) 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 Smathers Beach and Duval Street are located nearby.

Fairfield Inn and Suites by Marriott Key West

per person

Feb 21 - Feb 25

found 1 day ago

Roundtrip flight included

Boston (BOS) to Key West (EYW)

Stay at this hotel in Key West. Enjoy free breakfast, free WiFi, and a 24-hour fitness center. Our guests praise the breakfast and the pool in our reviews. Popular attractions Smathers Beach and Duval Street are located nearby.

Eden House

per person

Feb 21 - Feb 25

found 1 day ago

Roundtrip flight included

Boston (BOS) to Key West (EYW)

Stay at this 3.5-star hotel in Key West. Enjoy free WiFi, in-room massages, and a 24-hour front desk. Our guests praise the pool and the helpful staff in our reviews. Popular attractions Duval Street and Ernest Hemingway Home and Museum are located nearby.

3-4 Night Vacations in South Beach

Price found within the past 48 hours. Click for updated prices.