Key West Florida Vacation Rentals

Search 26 Key West rental beach homes & vacation condos.

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Key West Vacation Rentals

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GOT BEACH? Beach + Ocean View from Kingbed WOW!! IN
This Listing Qualifies for the Trusted Seal - All Information is up to date and the Owner in good standing.

Key West Florida

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  • Studio,
  • 0 Bedrooms,
  • Capacity 2,
  • $100 to $250 Per Night
View GOT BEACH Beach  Ocean View

You Found The Best Stay In Key West! For the best stay in Key West ever! You Got IT! Not a budget stay unless off season- Units overlook the Atlantic 24/7! See you soon in paradise here as you can look at the Atlantic ALL THE TIME! Ocean Ocean Ocean! We are hard to find at times even though our site keywestbeachfrontrental.com is front a...
Southern Comforts

Key West Florida

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  • Home,
  • 4 Bedrooms,
  • Capacity 8,
  • Over $250 Per Night
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4 bedroom, 2 baths ocean front home with a dock and an in-ground heated pool. Central air, all kitchen and bath amenities, to include washer and dryer. Located only 15 miles from Key West and all a...
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Dos Casas in Old Town Key West

Key West Florida

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  • Home,
  • 4 Bedrooms,
  • Capacity 8,
  • Over $250 Per Night
View Dos Casas in Old Town Key West

Why rent one when you can have two great houses? Dos Casas is a unique 4-bedroom property in the heart of the most beautiful part of Old Town. This lovely 2 house compound is just a few blocks from...
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Margaritavillas

Key West Florida

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  • Condo,
  • 3 Bedrooms,
  • Capacity 8,
  • $99 or Less Per Night
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1, 2, 3, 4, 5, 6 & 7 BR Luxury Villas in Historic Old Town Key West with Heated Pool, Full Kitchens, Parking and adjacent to the best beach in Key West. Quiet and peaceful, yet just 3 blocks from D...
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Paradise Island Villas

Key West Florida

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  • Home,
  • 3 Bedrooms,
  • Capacity 8,
  • $100 to $250 Per Night
View Paradise Island Villas

These Luxury Oceanfront Villas are among the absolute finest properties available anywhere in the Florida Keys, yet are moderately priced. Convenient location just 5 minutes from all activities by car...
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Poolside Beach Cottage in Old Town

Key West Florida

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  • Condo,
  • 2 Bedrooms,
  • Capacity 4,
  • $100 to $250 Per Night
View Poolside Beach Cottage in Old

2 BR, 1 BA Poolside Cottage at Fort Zachary Taylor State Park & Beach in Old Town Key West....
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The Hangover House

Key West Florida

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  • Home,
  • 3 Bedrooms,
  • Capacity 8,
  • Over $250 Per Night
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3 BR, 2 BA Private Home shares the pool with the 2 BR, 2 BA Hangover Cottage (rents separately).  Located just 4 blocks off Duval Street and close to Mallory Square and Fort Zachary Taylor Beach....
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The Hangover Cottage

Key West Florida

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  • Home,
  • 2 Bedrooms,
  • Capacity 6,
  • Over $250 Per Night
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2 BR, 2 BA Private Home shares the pool with the 3 BR, 2 BA Hangover House (rents separately). Located just 4 blocks off Duval Street and close to Mallory Square and Fort Zachary Taylor Beach....
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Poolside Villa 2 BR

Key West Florida

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  • Home,
  • 2 Bedrooms,
  • Capacity 6,
  • Over $250 Per Night
View Poolside Villa 2 BR

Deluxe 2 BR, 2 BA Home with Shared Pool and Jacuzzi. Located just 1/2 block off Duval street yet Quiet as there are no bars or restaurants next door. Located 1 block from Jimmy Buffett's Margaritav...
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One Lofty Villa

Key West Florida

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  • Home,
  • 1 Bedrooms,
  • Capacity 4,
  • Over $250 Per Night
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1 BR, 1 BA Private Cottage in the front of a small compound of cottages that share a Pool and Jacuzzi. Separate from the other units with it's own Covered Front Porch for People Watching! Located just...
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Waterfront 2/2 Penthouse Loft at the Galleon Resort

Key West Florida

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  • Resort,
  • 2 Bedrooms,
  • Capacity 8,
  • Over $250 Per Night
View Waterfront 22 Penthouse Loft

This 2 bedroom, 2 bath Penthouse Loft is located on the 5th floor overlooking the marina & harbor. On the first floor is a full size, fully equipped kitchen, breakfast nook, dining room, living roo...
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Galleon Resort at Budget Rates

Key West Florida

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  • Home,
  • 0 Bedrooms,
  • Capacity 2,
  • $100 to $250 Per Night
View Galleon Resort at Budget Rates

This Vacation Hideaway is located on the 5th floor of the Galleon Resort and Marina. Only one of two efficiencies at this resort with both a king size bed and a balcony (resort view). Features incl...
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Key West Retreat

Key West Florida

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  • Home,
  • 3 Bedrooms,
  • Capacity 6,
  • Over $250 Per Night
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This delightful Truman Annex home has mature palms and plants, surrounding a refreshing and roomy pool. Very conveniently located near Ft. Zachery Taylor, Mallory Sunset Pier and Duval Street restaur...
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Shipyard 2BR2BA Condo in Old Town Key West Truman Annex

Key West Florida

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  • Condo,
  • 2 Bedrooms,
  • Capacity 6,
  • $100 to $250 Per Night
View Shipyard 2BR2BA Condo in Old

Truman Annex is located in the heart of Key West's Old Town. Walking or biking distance from all the shops, restaurants, bars & attractions, you don't even need a car. Fly in and take a taxi from t...
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Emma House - 2b/2.5b ------ Add cottage to get 3b/3.5b

Key West Florida

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  • Home,
  • 3 Bedrooms,
  • Capacity 6,
  • Over $250 Per Night
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Location ! ! Location ! ! Location ! ! Emma House with Pvt Pool is located in Truman Annex Community which is one of the Best locations in Key West. You can walk...
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Tee by the Sea

Key West Florida

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  • Condo,
  • 2 Bedrooms,
  • Capacity 6,
  • $100 to $250 Per Night
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"TEE BY THE SEA" vacation rental (we include 6 bikes free for our guests!!!) If you love...GOLF, SPORT FISHING/BOATING, ART/THEATER AND FANTASTIC LIVE ENTERTAINMENT...than you'll love "Tee by the S...
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www.coconutpalmsofkeywest.com

Key West Florida

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  • Condo,
  • 2 Bedrooms,
  • Capacity 6,
  • Over $250 Per Night
View wwwcoconutpalmsofkeywestcom

Beautifully remodeled, 1374 sq. ft., 2 bedroom (King Beds) 2 Bathroom condo- Beautifully landscaped & LOCATED ON THE OCEAN-SLEEPS 6.    (RIGHT NEXT TO SMATHERS BEACH!) VISIT:    http://www.coconutp...
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Island Wind Tropical Townhome

Key West Florida

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  • Home,
  • 2 Bedrooms,
  • Capacity 4,
  • $100 to $250 Per Night
View Island Wind Tropical Townhome

Island Wind welcomes you to a tropical sun drenched oasis in the heart of Old Town. This charming Bahamian style townhome with tin roof and white spindled decks reminiscent of old Key West is located ...
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A Touch of Bermuda in Key West

Key West Florida

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  • Townhouse,
  • 2 Bedrooms,
  • Capacity 6,
  • Over $250 Per Night
View A Touch of Bermuda in Key West

Our Bermuda-style cottage is located in the Truman Annex which is quiet yet a short walking distance to the beach and pool and the excitement of Old Town. Lazy overhead fans turn in every room deco...
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Paradise in KEY WEST 2 Block walk to Duval ST

Key West Florida

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  • Condo,
  • 1 Bedrooms,
  • Capacity 4,
  • Over $250 Per Night
View Paradise in KEY WEST 2 Block

The Heron is one of several of the Colony Suites in historic Key West, Florida. A conch style cottage nestled in the heart of Historic Old Town Key West, just two blocks from the world famous Duval...
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Currently displaying listings 1 through 20 of 26 listings.

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