Vacations Close To Key West Historic Seaport

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Key West Historic Seaport Flight + Hotel packages

Price found within the past 48 hours. Click for updated prices.
The Pelican Key Largo Cottages

The Pelican Key Largo Cottages

2 out of 5
Price was $1,010, price is now $767 per person
$767
per person
Dec 23 - Dec 27
found 1 day ago
Roundtrip flight included
Cleveland (CLE) to Miami (MIA)
Great time

Reviewed on Nov 10, 2026

Orchid Key Inn - Adults Only

Orchid Key Inn - Adults Only

3.5 out of 5
Old Town Key West
Price was $2,125, price is now $1,388 per person
$1,388
per person
Dec 23 - Dec 27
found 1 day ago
Roundtrip flight included
Cleveland (CLE) to Key West (EYW)
Always enjoy our stay here. The drink selection at the bar are fantastic and the drinks themselves are delicious. Very clean property. A lot of attention to detail here

Reviewed on Nov 12, 2026

The Marker Key West Harbor Resort

The Marker Key West Harbor Resort

4 out of 5
Key West Historic District
Price was $1,852, price is now $1,247 per person
$1,247
per person
Dec 23 - Dec 27
found 1 day ago
Roundtrip flight included
Cleveland (CLE) to Key West (EYW)

The Perry Hotel & Marina Key West

The Perry Hotel & Marina Key West

4 out of 5
Price was $1,350, price is now $911 per person
$911
per person
Dec 23 - Dec 27
found 1 day ago
Roundtrip flight included
Cleveland (CLE) to Key West (EYW)

Southernmost House - Adult Exclusive

Southernmost House - Adult Exclusive

4 out of 5
Old Town Key West
Price was $2,073, price is now $1,495 per person
$1,495
per person
Dec 23 - Dec 27
found 1 day ago
Roundtrip flight included
Cleveland (CLE) to Key West (EYW)
Stunning, I dont have to say anymore

Reviewed on Nov 10, 2026

Seascape Resort & Marina

Seascape Resort & Marina

3 out of 5
Price was $1,416, price is now $1,029 per person
$1,029
per person
Dec 23 - Dec 27
found 1 day ago
Roundtrip flight included
Cleveland (CLE) to Miami (MIA)
Nice relaxing grounds! Our room was newly renovated, very clean and comfy bed. Friendly staff. We would definitely stay here again.

Reviewed on Nov 4, 2026

Blue Flamingo Resort Key West

Blue Flamingo Resort Key West

4 out of 5
New Town
Price was $1,295, price is now $957 per person
$957
per person
Dec 23 - Dec 27
found 1 day ago
Roundtrip flight included
Cleveland (CLE) to Key West (EYW)

Southernmost Beach Resort and Guesthouses

Southernmost Beach Resort and Guesthouses

4 out of 5
Old Town Key West
Price was $1,677, price is now $1,243 per person
$1,243
per person
Dec 23 - Dec 27
found 1 day ago
Roundtrip flight included
Cleveland (CLE) to Key West (EYW)
Great stay, friendly staff, lots of fun! We will Be back

Reviewed on Nov 12, 2026

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Best Lodging Options Near Key West Historic Seaport

The Marker Key West Harbor Resort

The Marker Key West Harbor Resort

4 out of 5
200 William Street Key West FL
0.03 km from Key West Historic Seaport
Book a stay at this business-friendly hotel in Key West. Enjoy free WiFi, 3 outdoor pools, and breakfast (surcharge). Our guests praise the pool and the helpful ...
La Concha Key West, Autograph Collection

La Concha Key West, Autograph Collection

4 out of 5
430 Duval St Key West FL
0.57 km from Key West Historic Seaport
Book a stay at this business-friendly hotel in Key West. Enjoy free WiFi, 3 restaurants, and 2 bars/lounges. Our guests praise the helpful staff and the clean ...
Pier House Resort & Spa

Pier House Resort & Spa

4 out of 5
1 Duval St Key West FL
0.52 km from Key West Historic Seaport
Book a stay at this beach resort in Key West. Enjoy a full-service spa, a private beach, and 2 bars/lounges. Our guests praise the pool and the helpful staff ...
Hyatt Centric Key West Resort and Spa

Hyatt Centric Key West Resort and Spa

4 out of 5
601 Front St Key West FL
0.3 km from Key West Historic Seaport
Book a stay at this beach resort in Key West. Enjoy free WiFi, a full-service spa, and a marina. Our guests praise the pool and the helpful staff in our reviews. ...
Opal Key Resort & Marina, Key West

Opal Key Resort & Marina, Key West

4 out of 5
245 Front Street Key West FL
0.62 km from Key West Historic Seaport
Stay at this hotel in Key West. Enjoy a marina, 3 bars/lounges, and breakfast (surcharge). Our guests praise the helpful staff and the clean rooms in our reviews. ...
Amsterdam's Curry Mansion Inn

Amsterdam's Curry Mansion Inn

3 out of 5
511 Caroline St Key West FL
0.4 km from Key West Historic Seaport
Book a stay at this historic guesthouse in Key West. Enjoy free WiFi, beach cabanas (surcharge), and a business center. Our guests praise the pool and the clean ...
Westwinds Inn

Westwinds Inn

3.5 out of 5
914 Eaton St Key West FL
0.33 km from Key West Historic Seaport
Stay at this hotel in Key West. Enjoy free breakfast, free WiFi, and 2 outdoor pools. Our guests praise the breakfast and the pool in our reviews. Popular attractions ...
Ocean Key Resort - A Noble House Resort

Ocean Key Resort - A Noble House Resort

4 out of 5
Zero Duval St. Key West FL
0.59 km from Key West Historic Seaport
Book a stay at this spa resort in Key West. Enjoy free WiFi, a full-service spa, and 2 restaurants. Our guests praise 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.