Vacations Close To South Beach

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South Beach Flight + Hotel packages

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

The Grand Guesthouse

2.5 out of 5
Old Town Key West
Price was $1,664, price is now $1,415 per person
$1,415
per person
Nov 11 - Nov 15
found 8 hours ago
Roundtrip non-stop flight included
Boston (BOS) to Key West (EYW)

The Key West Hotel

The Key West Hotel

3 out of 5
Key West Historic District
Save 100% on your flight
Price was $4,067, price is now $2,974 per person
$2,974
per person
Nov 11 - Nov 15
found 8 hours ago
Roundtrip non-stop flight included
Boston (BOS) to Key West (EYW)
Great place to stay - highly recommend.

Reviewed on Aug 20, 2026

The Marker Key West Harbor Resort

The Marker Key West Harbor Resort

4 out of 5
Key West Historic District
Price was $2,842, price is now $2,170 per person
$2,170
per person
Nov 11 - Nov 15
found 8 hours ago
Roundtrip non-stop flight included
Boston (BOS) to Key West (EYW)
Room at arrival was clean, but after not being washing

Reviewed on Sep 19, 2026

Southernmost Beach Resort and Guesthouses

Southernmost Beach Resort and Guesthouses

4 out of 5
Old Town Key West
Price was $2,667, price is now $2,095 per person
$2,095
per person
Nov 11 - Nov 15
found 8 hours ago
Roundtrip non-stop flight included
Boston (BOS) to Key West (EYW)

Southernmost House - Adult Exclusive

Southernmost House - Adult Exclusive

4 out of 5
Old Town Key West
Price was $3,276, price is now $2,706 per person
$2,706
per person
Nov 11 - Nov 15
found 8 hours ago
Roundtrip non-stop flight included
Boston (BOS) to Key West (EYW)

The Perry Hotel & Marina Key West

The Perry Hotel & Marina Key West

4 out of 5
Price was $1,863, price is now $1,551 per person
$1,551
per person
Nov 11 - Nov 15
found 8 hours ago
Roundtrip non-stop flight included
Boston (BOS) to Key West (EYW)

Suncoast House by Brightwild Pool Boat Dock

Suncoast House by Brightwild Pool Boat Dock

2 out of 5
Save 100% on your flight
Price was $6,749, price is now $5,623 per person
$5,623
per person
Nov 11 - Nov 15
found 8 hours ago
Roundtrip non-stop flight included
Boston (BOS) to Key West (EYW)

Amsterdam's Curry Mansion Inn

Amsterdam's Curry Mansion Inn

3 out of 5
Key West Historic District
Price was $1,854, price is now $1,579 per person
$1,579
per person
Nov 11 - Nov 15
found 8 hours ago
Roundtrip non-stop flight included
Boston (BOS) to Key West (EYW)
The Curry is so convenient to everyiwe want to do while in Key West.

Reviewed on Sep 20, 2026

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Best Lodging Options Near South Beach

Southernmost Beach Resort and Guesthouses

Southernmost Beach Resort and Guesthouses

4 out of 5
1319 Duval Street Key West FL
0.17 km from South Beach
Book a stay at this spa 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 ...
Southwinds Motel

Southwinds Motel

2 out of 5
1321 Simonton Street Key West FL
0.16 km from South Beach
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. ...
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
0.53 km from South Beach
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 South Beach ...
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
0.14 km from South Beach
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 Southernmost Inn - Adults Only

The Southernmost Inn - Adults Only

3 out of 5
525 United Street Key West FL
0.23 km from South Beach
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. ...
Douglas House - Adults Only

Douglas House - Adults Only

3 out of 5
419 Amelia St Key West FL
0.43 km from South Beach
Stay at this guesthouse in Key West. Enjoy free WiFi, daily housekeeping, and a garden. Popular attractions Duval Street and Ernest Hemingway Home and Museum ...
Southernmost House - Adult Exclusive

Southernmost House - Adult Exclusive

4 out of 5
1400 Duval Street Key West FL
0.1 km from South Beach
Book a stay at this beach hotel in Key West. Enjoy free WiFi, parking (surcharge), and daily housekeeping. Our guests praise the helpful staff and the property ...
Santa Maria Suites

Santa Maria Suites

4 out of 5
1401 Simonton St Key West FL
0.11 km from South Beach
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 ...
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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.