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Key West, Florida Vacations & Travel Packages

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Classic Harbor Line Key West, Florida Sailing & Yacht Charters

Classic Harbor Line

Key West, Florida Sailing & Yacht Charters

Classic Harbor Line proudly runs Schooner America 2.0, the premier sailing vessel in Key West, featuring two-hour sunset and day sails. Complimentary drinks and hors d'oeuvres provided.

From USD $
55
per Trip
Key West Bed and Breakfast Key West, Florida Bed & Breakfasts

Key West Bed and Breakfast

Key West, Florida Bed & Breakfasts

Classic Caribbean Casual

From USD $
110
per Night
Curry House Key West, Florida Bed & Breakfasts

Curry House

Key West, Florida Bed & Breakfasts

The Curry House is one of the old, historic homes of a bygone era. Immaculately kept in a quiet, centrally located part of Old Town. After a day, (or night), of fun and excitement on the town or on the water, escape to your own tropical hideaway.

From USD $
99
per Night
Rose Lane Villas Key West, Florida Vacation Rentals

Rose Lane Villas

Key West, Florida Vacation Rentals

Bedrooms: 1  Sleeps: 4  Bathrooms: 1  
Rose Lane Villas is located in the heart of Old Town Key West, only half a block from Duval Street. These 1, 2 and 3 bedroom villas feature fully equipped kitchens, living rooms, complimentary parking...

From USD $
249
per Night
Old Town Manor Key West, Florida Bed & Breakfasts

Old Town Manor

Key West, Florida Bed & Breakfasts

Old Town Manor, formerly Eaton Lodge, is ideally located just steps off of Duval Street in the heart of Old Town Key West near Mallory Square, Sloppy Joe’s, and Margaritaville. Built in 1886, our classic setting and location can't be beat.

From USD $
135
per Night
Old Town Manor Weddings Key West, Florida Destination Weddings & Coordinators

Old Town Manor Weddings

Key West, Florida Destination Weddings & Coordinators

Create an exclusive experience for your wedding guests by booking this 14 room guest house as your wedding "headquarters." Our lush gardens can accommodate up to 75 guests! We proudly support and offer our services to LGBTQ weddings.

From USD $
2,500
per Trip
Old Customs House Inn &  the Smallest Bar Key West, Florida Bed & Breakfasts

Old Customs House Inn & the Smallest Bar

Key West, Florida Bed & Breakfasts

Old Customs House Inn & the Smallest Bar is a cozy Inn located in historic downtown "Old Town Key West", right in the middle of nearly everything Key West has to offer yet offers a semi-tropical getaway 130 miles from the mainland of Florida.

From USD $
99
per Night
Clothing Optional Gay B and B Key West, Florida Bed & Breakfasts

Clothing Optional Gay B and B

Key West, Florida Bed & Breakfasts

The New Orleans House is the only gay all male guest house on Duval St. Located in the heart of Old Town Key West just steps from everything Key West offers. From shopping and fine art gallery's to the exciting nightlife and variety of entertainment

Contact For Rates & Specials!
Florida Keys Women's Adventure Key West, Florida Kayaking & Canoeing

Florida Keys Women's Adventure

Key West, Florida Kayaking & Canoeing

This fun-loving adventure gives you a taste of the Florida Keys—from Miami all the way down to Key West! Enjoy kayaking, wine tasting, snorkeling, eco tours, island food and more, all in the company of new friends and guided by knowledgeable locals

From USD $
350
per Night
Truman Annex Key West Key West, Florida Vacation Rentals

Truman Annex Key West

Key West, Florida Vacation Rentals

Your blender is waiting at the beautiful Truman Annex “MARGARITA VILLAS”

From USD $
1,000
per Week




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Key West, Florida Vacations & Travel Packages

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