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Budget to luxury Key West, Florida travel and vacations. Search all the best vacation options in Key West including accommodations, adventure travel, unique tours and much more.


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Featured Listings

1 - 20 of 48 within 100 miles of Key West, Florida
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 offe...
From USD $2,500 per trip

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
Lone Palm Old Town Key West Vacation Home Rental Key West, Florida Vacation Rentals

Lone Palm Old Town Key West Vacation Home Rental

Key West, Florida Vacation Rentals
Bedrooms: 2  Sleeps: 6  Bathrooms: 2  
Welcome to Paradise! Modern 2 bed 2 bath vacation home rental accommodations with a tropical flare. A block off Duval in Windward Park. 50 ft pool/BBQ/ hot tub. Walking distance to all the attraction...
From USD $2,500 per week
Key West Hideaways Key West, Florida Vacation Rentals

Key West Hideaways

Key West, Florida Vacation Rentals
Bedrooms: 2  Sleeps: 6  Bathrooms: 2  
Experience the uniqueness of Key West by staying at one of Key West Hideaway’s one-of-a-kind vacation rentals. When you’re ready to escape the hustle and bustle of the “real world” why not enj...
From USD $188 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 cl...
From USD $135 per night
Key West, Rental by Owner in Truman Annex Key West, Florida Vacation Rentals

Key West, Rental by Owner in Truman Annex

Key West, Florida Vacation Rentals
Bedrooms: 3  Sleeps: 6  Bathrooms: 3  
Emma House can be rented in 2 ways. Emma House by itself is a 3 bedroom & 2.5 bath unit or Emma House with the Cottage creates a 4 bedroom and 3.5 bath retreat. It is deluxe unit with Tropical Keys St...
Contact For Rates & Specials!
Key West Vacation Rental near Duval Street Key West, Florida Vacation Rentals

Key West Vacation Rental near Duval Street

Key West, Florida Vacation Rentals
Bedrooms: 1  Sleeps: 4  Bathrooms: 1  
A one bedroom, one bath home with pool only 2 blocks from Duval!...
From USD $188 per night
Orchid Key Inn Key West, Florida Bed & Breakfasts

Orchid Key Inn

Key West, Florida Bed & Breakfasts
Location, Location, Location... Four Star service and amenities... Off-street parking.... Complimentary breakfast and Happy hour... Luxurious guest rooms... Full service " Orchid Bar......
Contact For Rates & Specials!
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
Ocean Breeze Inn Key West, Florida Bed & Breakfasts

Ocean Breeze Inn

Key West, Florida Bed & Breakfasts
Located in Old Town Key West, just steps away from beaches, restaurants, nightlife and all major attractions.This charming inn has 15 rooms, all located on the ground floor with a private entrance....
Contact For Rates & Specials!
Smallest Bar Inn &  the Smallest Bar Key West, Florida Bed & Breakfasts

Smallest Bar Inn & the Smallest Bar

Key West, Florida Bed & Breakfasts
Smallest Bar 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 1...
From USD $99 per night
DoubleTree by Hilton Grand Key Resort Key West, Florida Hotels & Resorts

DoubleTree by Hilton Grand Key Resort

Key West, Florida Hotels & Resorts
DoubleTree by Hilton Hotel Grand Key Resort, where a friendly staff welcomes you with our famous token of hospitality " a freshly baked chocolate chip cookie. Our newly renovated full service resort...
From USD $199 per night

Dolphin Encounter with Wild about Dolphins Key West, Florida Eco Tours

Dolphin Encounter with Wild about Dolphins

Key West, Florida Eco Tours
Experience wild dolphins, snorkel coral reefs & explore the backcountry islands in Key West, Florida....
Contact For Rates & Specials!
Pilot House Guest House Key West, Florida Bed & Breakfasts

Pilot House Guest House

Key West, Florida Bed & Breakfasts
A tropical oasis in Old Town Key West. From our grand two-story Victorian Mansion built circa 1900 to our modern pool-front Cabana Building, the Pilot House has everything you need....
Contact For Rates & Specials!
Truman Annex Key West Key West, Florida Vacation Rentals

Truman Annex Key West

Key West, Florida Vacation Rentals
Bedrooms: 2  Sleeps: 4  Bathrooms: 1  
Your blender is waiting at the beautiful Truman Annex “MARGARITA VILLAS”...
From USD $1,000 per week
Island Wind Key West Vacation Home Rentals Key West, Florida Vacation Rentals

Island Wind Key West Vacation Home Rentals

Key West, Florida Vacation Rentals
Bedrooms: 2  Sleeps: 5  Bathrooms: 2  
Key West vacation home rentals in the heart of Old Town. 2 bed 2 bath conch home a block off Duval in Windward Park a gated community of 13 homes clustered around a 50 foot pool. Within walking dist...
From USD $175 per night
Nature:Boat,Fishing,Photo,Sunset,Birding,EcoTours Chokoloskee, Florida Fishing Trips

Nature:Boat,Fishing,Photo,Sunset,Birding,EcoTours

Chokoloskee, Florida Fishing Trips - 87.1 miles away
We cater to the smaller, more personal, group Eco Tours. Max passangers is 3. Boat Assisted Photo Tours,Birding Tours,Sunset Tours,Out Island Beach Walks and Fishing. Prices very depending on type ...
Contact For Rates & Specials!
Everglades fishing charters at no free lunch chart Chokoloskee, Florida Fishing Trips

Everglades fishing charters at no free lunch chart

Chokoloskee, Florida Fishing Trips - 87.0 miles away
Light tackle and fly fishing charters in the coastal waters of everglades national park. Birding and photography tours....
From USD $375 per trip
Village at Hawks Cay Villas by KeysCaribbean Duck Key, Florida Vacation Rentals

Village at Hawks Cay Villas by KeysCaribbean

Duck Key, Florida Vacation Rentals - 49.8 miles away
Bedrooms: 2  Sleeps: 6  Bathrooms: 2  
Stay at Hawks Cay with Huge Savings in the heart of the Florida Keys, the Village at Hawks Cay Villas offers an authentic island vacation, for romantic getaways, family reunions, destination weddings,...
From USD $199 per night


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