Key West Vacations & Travel Packages

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1 - 20 of 75 within 100 miles of Key West, Florida  
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Featured Listings

Trumpy Yacht Charters
Newport, Rhode Island Luxury Cruises - 6.6 mi away
Classic yacht cruising vacations in New England & Florida Book a private charters on the beautifully restored Trumpy motor yacht Lady Catherine, complete with Captain & cook. Luxurious staterooms, it...
From USD $10,000 per week
Sky Dive Key West
Key West, Florida Skydiving - 6.6 mi away
Contact For Rates & Specials!
Key West Oasis 2 block walk to Duval Street
Key West, Florida Vacation Rentals - 7.6 mi away
Bedrooms: 1  Sleeps: 4  Bathrooms: 1  
This Hidden Oasis is just a short 2 block walk to Duval street and all the action Key West has to offer. Fully equipped with everything you need to just RELAX. The Blender is waiting for your margar...
3 reviews
From USD $195 per night

The Gardens Hotel
Key West, Florida Hotels & Resorts - 7.8 mi away
Immerse yourself in the luxurious island lifestyle offered at The Gardens Hotel Key West. Our boutique hotel offers 20 uniquely decorated guestrooms, as well as impressive amenities such as a self-ser...
From USD $199 per night
Old Town Manor Weddings
Key West, Florida Destination Weddings & Coordinators - 7.9 mi away
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
Smallest Bar Inn &  the Smallest Bar
Key West, Florida Bed & Breakfasts - 8.0 mi away
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
Parmer's Resort
Little Torch Key, Florida Hotels & Resorts - 19.4 mi away
Come back to the Florida Keys of Yesteryear... Parmer's Resort, a unique collection of rooms, suites and cottages on the ocean. Escape from your busy life, lounge by the pool, nap in a hammock, bring ...
From USD $139 per night
Flats/Backcountry Fishing Guide Fly & Spin
Islamorada, Florida Fishing Trips - 34.9 mi away
I am a fully licensed & insured professional proven fishing guide for every angler, novice & seasoned, spin & fly, flats or backcountry in the upper Florida Keys & have a restored 18' poling skiff for...
From USD $500 per trip
Kings Kamp Rv Park, Motel & Marina
Key Largo, Florida Campgrounds & RV Parks - 88.8 mi away
Our Recreational Vehicle sites are right on the open water of Florida Bay and located adjacent to the Marina for easy access to your boat. The waterfront location provides spectacular views....
Contact For Rates & Specials!

Marco Island Waterfront Fun Anglers Cove Resort
Marco Island, Florida Vacation Rentals - 93.0 mi away
Bedrooms: 1  Sleeps: 6  Bathrooms: 1  
By Owner. No Agency Fees. Updated Marco River Waterfront Condos. Tennis Cts, Pools(Heated), Spas, Marina w/Boat Slips. Waterfront Dining & Tiki Bar. Very Tropical! Marco Beaches 5 min. Golf & Naples 5...
From USD $600 per week
Everglades Hostel & Tours
Florida City, Florida Youth Hostels - 95.9 mi away
Take a trip into the heart of the Everglades by canoe or just relax in our gardens. The hostel has many types of lodging plus Canoe rentals, Wilderness Waterway Shuttles, Guided Everglades Trips w/ Ca...
From USD $28 per night
I'm Your Trip
Miami, Florida Surfing - 124.9 mi away
We are an adventure travel agency specialized in adventure sports trips for solo travelers worldwide. We are located in Miami, Florida USA. We provide solo adventure sports trips in their 30s and 40s ...
Contact For Rates & Specials!
3 Room Art Deco Oceanfront Suite at Shelborne
Miami Beach, Florida Vacation Rentals - 128.0 mi away
Bedrooms: 3  Sleeps: 8  Bathrooms: 1  
We are happy to offer you accommodation in Shelborne with 'the best location' next to Lincoln Road and only a couple of blocks to Ocean Drive in South Beach Miami Art Deco district that can create nic...
From USD $1,390 per week
Everglades Private Airboat Tour
Pembroke Pines, Florida Eco Tours - 136.7 mi away
Relax and enjoy a beautiful trip thru the Heart of the Everglades. All tours guided by a multi-generation Gladesmen who knows all this World Heritage Site has to offer its guests. Our unique location ...
From USD $199 per trip
hot travel deals
Walk About Beach Resort
Hollywood, Florida, Florida Hotels & Resorts - 139.6 mi away
The Walkabout is known for its remarkable beachfront setting and legendary Hollywood Beach, Florida hotel location - on the Broadwalk. Named one of America's best beach Broadwalks by Travel + Leisure,...
From USD $199 per night

Additional Listings

Dolphin Encounter with Wild about Dolphins
Key West, Florida Eco Tours - 3.4 mi away
Experience wild dolphins, snorkel coral reefs & explore the backcountry islands in Key West, Florida....
Contact For Rates & Specials!
DoubleTree by Hilton Grand Key Resort
Key West, Florida Hotels & Resorts - 4.7 mi away
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
Swim with Dolphins at Dolphin World
Florida Keys, Florida Eco Tours - 5.5 mi away
Dolphin World - Your complete dolphin encounter and dolphin vacation place. Complete Dolphin packages available, Adventure, Romance, Engagement, and Spa, which includes activities, hotel and transport...
From USD $79 per trip
Classic Harbor Line
Key West, Florida Sailing & Yacht Charters - 6.6 mi away
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, Rental by Owner in Truman Annex
Key West, Florida Vacation Rentals - 6.7 mi away
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!


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