Key West: the End of the Road and the Beginning of Adventure!

The Southernmost City attracts those who love the year round warm Atlantic Ocean and all the exciting watersports – sailing, to sportfishing, snorkeling and SCUBA diving, kite surfing and stand up boarding, kayaking – as well as those who just love to relax on the beach or by the pool and save up their energy for the night’s Duval Crawl.

Key West nightlife and restaurants are just one more attraction to the Southernmost City. You don’t want to miss Key West best known watering hole, Sloppy Joe’s – famous for its toga parties, rocking music all day and night and its celebrated patron – Ernest “Papa” Hemingway. Hemingway cruised here from Europe with his new wife, expecting to pick up a car that was late in delivery. While the recently, married couple waited for the new car to show up, Hemingway discovered the incredible ocean and the opportunities for deep sea fishing that would become a lifelong pursuit of the famous author.

"Papa called" Key West the “poor man’s St. Tropez,” but today, most of the island’s beautiful historic homes have been renovated and restored to their 19th Century glory. In fact, Key West’s architecture and history is the attraction for many tourists. Visitors can tour the Oldest House, built circa 1829, Hemingway’s House and Gardens, the Audubon House built by wrecking captain John Geiger, and Truman’s Little White House.

Save on restaurants, attractions, golf, tours, recreation and more with FREE Florida Keys/Key West discount coupons from SavingsOnArrival.com.

Come and live like a local in a variety of Key West rentals. See sights and sounds, by bike or by foot that you wouldn’t be privy to in a stuffy overpriced hotel. Find beach homes, cottages, condos and more that are just right for families, couples and friends.

Key West is the island where anything goes and everyone who comes to play wants to stay.

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Key West Vacation Rental Accommodations - Page 1 of 9

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SPECIAL OFFER! LAST MINUTE SPECIALS...SAVE HUNDREDS May 10 - August 29

Key West Oceanfront Condominium - Key West Oceanfront at the Coral Reef

  • 2 BR/2 BA Condo (sleeps 6)
    $250 - $485/nt
    $1,395 - $3,395/wk
    per property, accept credit card, wheelchair accessible, Beach, Near The Ocean, Resort, Waterfront, Private Pool, Jacuzzi, Sauna, Tennis Court, terrace

Key West Luxurious 4 bedroom/3 full bath home with private pool in Old Town Truman Annex

  • 4 BR/3 BA Townhome (sleeps 8)
    $414 - $786/nt
    $2,900 - $4,900/wk
    per property, accept credit card, Downtown, Near The Ocean, Private Pool, Lawn / Garden, Balcony, Air Conditioning, Internet, Satellite / Cable

Key West Sunset and Ocean View in Key West's Truman Annex with 2 Bikes and Pool Access

  • 2 BR/1 BA Condo (sleeps 4)
    $1,400 - $2,050/wk
    $4,800 - $7,000/month
    per property, accept credit card, Near The Ocean, Town, Communal Pool, Balcony, Air Conditioning, Internet, Satellite / Cable, Television

Key West Spacious Two Bedroom In Casa Marina Resort

  • 2 BR/2 BA Villa (sleeps 8)
    $400/nt
    $2,800/wk
    $11,000/month
    per property, Hot Tub, Communal Pool, Sauna, Internet, Satellite / Cable, Television, DVD Player, Parking

Key West Real World MTV House---Not Just a House Your Own Private Resort

  • 10 BR/5 BA, 1 half bath House (sleeps 20)
    $1,500 - $2,500/nt
    $10,000 - $12,500/wk
    $40,000 - $50,000/month
    per property, accept credit card, pets considered, Hot Tub, Resort, Waterfront, Jacuzzi, Tennis Court, Lawn / Garden, Balcony

Key West The Victoria House: 5 BR / 5.5 BA house in Key West, Sleeps 12

  • 5 BR/5 BA, 1 half bath House (sleeps 12)
    $865 - $1,776/nt
    $5,800 - $12,035/wk
    per property, Hot Tub, Private Pool, Air Conditioning, Internet, Television, DVD Player, Parking

Key West Southard Charm: 3 BR / 2.0 BA house in Key West, Sleeps 8

  • 3 BR/2 BA House (sleeps 8)
    $400 - $855/nt
    $2,650 - $5,872/wk
    per property, pets considered, Private Pool, Air Conditioning, Television, DVD Player

Key West A Place in Paradise: 2 BR / 2.5 BA condo in Key West, Sleeps 6

  • 2 BR/2 BA, 1 half bath Condo (sleeps 6)
    $1,550 - $3,443/wk
    per property, Communal Pool, Air Conditioning, Television, DVD Player, Parking

Key West Crowner's Jewel: 2 BR / 2.5 BA condo in KEY WEST, Sleeps 6

  • 2 BR/2 BA, 1 half bath Condo (sleeps 6)
    $1,550 - $3,081/wk
    per property, Communal Pool, Air Conditioning, Internet, DVD Player, Parking

Key West Bahama Dreaming: 3 BR / 2.0 BA house in Key West, Sleeps 8

  • 3 BR/2 BA House (sleeps 8)
    $465 - $906/nt
    $2,925 - $6,017/wk
    per property, pets considered, Private Pool, Air Conditioning, Internet, Television, DVD Player, Parking

Key West Bahamian Reed: 2 BR / 1.5 BA condo in Key West, Sleeps 5

  • 2 BR/1 BA, 1 half bath Condo (sleeps 5)
    $1,350 - $3,045/wk
    per property, Communal Pool, Air Conditioning, Internet, Television, DVD Player, Parking

Key West Coral Caribe: 2 BR / 2.5 BA condo in Key West, Sleeps 6

  • 2 BR/2 BA, 1 half bath Condo (sleeps 6)
    $150 - $337/nt
    $900 - $2,093/wk
    per property, pets considered, Hot Tub, Private Pool, Communal Pool, Air Conditioning, Internet, DVD Player, Parking

Key West Easy Livin': 3 BR / 4.0 BA house in Key West, Sleeps 8

  • 3 BR/4 BA House (sleeps 8)
    $4,000 - $9,200/wk
    per property, Private Pool, Air Conditioning, Television, DVD Player, Parking

Key West Conch Condo: 2 BR / 2.0 BA condo in Key West, Sleeps 4

  • 2 BR/2 BA Condo (sleeps 4)
    $1,350 - $2,972/wk
    per property, Communal Pool, Air Conditioning, Parking

Key West Parrot Perch: 2 BR / 2.0 BA condo in KEY WEST, Sleeps 5

  • 2 BR/2 BA Condo (sleeps 5)
    $1,175 - $2,718/wk
    per property, Communal Pool, Air Conditioning, Television, Parking

Key West The Hemingway: 2 BR / 2.0 BA condo in Key West, Sleeps 6

  • 2 BR/2 BA Condo (sleeps 6)
    $1,350 - $3,045/wk
    per property, Private Pool, Communal Pool, Air Conditioning

Key West Brisa del Mar: 2 BR / 2.0 BA condo in Key West, Sleeps 6

  • 2 BR/2 BA Condo (sleeps 6)
    $225 - $387/nt
    $1,300 - $2,381/wk
    per property, Hot Tub, Communal Pool, Air Conditioning, Internet, Television, Parking

Key West Luxury 2 Bedroom 2.5 Bath Condo On Duval Street. Great Location 'NEW LISTING'

  • 2 BR/2 BA, 1 half bath Condo (sleeps 4)
    $365 - $495/nt
    $2,236 - $3,150/wk
    $8,944 - $12,150/month
    per property, wheelchair accessible, Downtown, Communal Pool, Balcony, Air Conditioning, Internet, Satellite / Cable, Television

Key West 2 Bed / 2 Bath Luxury Condo on the Ocean - Sleeps 6 (next to Smather's Beach)

  • 2 BR/2 BA Condo (sleeps 6)
    $220 - $400/nt
    $1,540 - $2,520/wk
    $4,500 - $7,500/month
    per property, accept credit card, Hot Tub, wheelchair accessible, Beach, Near The Ocean, Resort, Communal Pool, Jacuzzi, Sauna, Tennis Court

Key West Bargain Rates in Truman Annex - Heart of Old Town, Key West

  • 2 BR/1 BA Condo (sleeps 6)
    $245 - $425/nt
    $1,395 - $2,400/wk
    per property, accept credit card, Beach, Near The Ocean, Communal Pool, Air Conditioning, Internet, Satellite / Cable, Television, DVD Player

Key West Key West vacation townhouse rental in the Truman Annex

  • 2 BR/2 BA, 1 half bath Townhome (sleeps 6)
    $1,400 - $3,300/wk
    $5,500 - $9,500/month
    per property, accept credit card, Downtown, Near The Ocean, Communal Pool, Balcony, Air Conditioning, Internet, Satellite / Cable, Television

Key West Key West ocean view 3 bedroom Truman Annex vacation condo

  • 3 BR/3 BA Condo (sleeps 6)
    $3,300 - $6,000/wk
    $11,000 - $17,000/month
    per property, accept credit card, wheelchair accessible, Downtown, Waterfront, Communal Pool, Balcony, Air Conditioning, Internet, Satellite / Cable

Key West KEY WEST LIVIN' Beautiful 50' Yacht 3 Bed, 2 Bath Sleeps 6 WIFI,Beach,Pool, Gym

  • 3 BR/2 BA Yacht (sleeps 8)
    $275 - $450/nt
    per property, pets considered, Resort, Communal Pool, Sauna, Fitness Room / Equipment, Air Conditioning, Internet, Satellite / Cable

Key West Attitude Key West At the Beach

  • 1 BR/1 BA Condo (sleeps 4)
    $165 - $357/nt
    $1,050 - $2,500/wk
    per property, accept credit card, Hot Tub, wheelchair accessible, Beach, Downtown, Near The Ocean, Resort, Town, Waterfront, Communal Pool, Sauna, Lawn / Garden, Balcony

Key West Dock, Htd 80' Pool, Deep Channel, 15 Min To Key West

  • 2 BR/2 BA Bungalow (sleeps 6)
    $995 - $1,600/wk
    per property, accept credit card, Hot Tub, Communal Pool, Air Conditioning, Internet, Satellite / Cable, Television, Parking

Key West Coral Hammock - Beautiful Home at the entrance to Key West (35)

  • 2 BR/2 BA, 1 half bath Townhome (sleeps 4)
    $225 - $275/nt
    $1,200 - $1,500/wk
    per property, accept credit card, Near The Ocean, Communal Pool, Balcony, Fitness Room / Equipment, Air Conditioning, Internet, Satellite / Cable

Key West Love Lane - private cottage on a quiet lane in Old Town

  • Studio House (sleeps 6)
    $5,600 - $11,200/month
    per property, Private Pool, Air Conditioning, Internet, Satellite / Cable, Television, DVD Player, Parking

Key West TREETOPS: Steps to DUVAL ST+3BR +2BA +POOL +WIFI+Private HOME+2 FREE Bikes+HDTVs

  • 3 BR/2 BA Cottage (sleeps 6)
    $3,547 - $5,600/month
    per property, Communal Pool, Balcony, Air Conditioning, Internet, Satellite / Cable, Television, Parking

Key West A little piece of Paradise in the Truman Annex

  • 2 BR/1 BA Condo (sleeps 6)
    $980 - $3,000/wk
    per property, Beach, Downtown, Near The Ocean, Communal Pool, Air Conditioning, Internet, Satellite / Cable, Television, DVD Player, Parking

Key West Namaste Key West - Tropical Retreat in a Key West Conch Cottage

  • 2 BR/1 BA Cottage (sleeps 4)
    $2,500 - $5,000/month
    per property, accept credit card, pets considered, Beach, Downtown, Lawn / Garden, Air Conditioning, Internet, Satellite / Cable, Television

Key West Tranquility: 1 BR / 1.5 BA house in Key West, Sleeps 3

  • 1 BR/1 BA, 1 half bath House (sleeps 3)
    $210 - $413/nt
    $1,175 - $2,465/wk
    per property, Communal Pool, Air Conditioning, Internet, Television, DVD Player

Key West Key West Ginger House

  • 2 BR/2 BA House (sleeps 6)
    $215 - $435/nt
    $1,300 - $2,718/wk
    per property, pets considered, Hot Tub, Air Conditioning, Internet, Television, DVD Player, Parking

Key West Finn Key: 2 BR / 1.0 BA condo in Key West, Sleeps 4

  • 2 BR/1 BA Condo (sleeps 4)
    $1,175 - $2,682/wk
    per property, Communal Pool, Air Conditioning, Internet, Television, Parking

Key West Artist Garden: 2 BR / 2.5 BA house in Key West, Sleeps 6

  • 2 BR/2 BA, 1 half bath House (sleeps 6)
    $1,800 - $3,697/wk
    per property, Communal Pool, Air Conditioning, Internet, DVD Player, Parking

Key West Duval Breeze: 2 BR / 2.5 BA condo in Key West, Sleeps 6

  • 2 BR/2 BA, 1 half bath Condo (sleeps 6)
    $225 - $456/nt
    $1,350 - $2,863/wk
    per property, Communal Pool, Air Conditioning, Television, DVD Player, Parking

Key West Duval Sea Turtle: 2 BR / 2.5 BA condo in Key West, Sleeps 6

  • 2 BR/2 BA, 1 half bath Condo (sleeps 6)
    $225 - $456/nt
    $1,350 - $2,863/wk
    per property, Communal Pool, Air Conditioning, Internet, DVD Player, Parking

Key West Garden Oasis Has A Large Tranquil Garden For Outside Enjoyment.

  • 2 BR/1 BA Condo (sleeps 4)
    $200 - $250/nt
    per property, Beach, Near The Ocean, Village, Communal Pool, Air Conditioning, Internet, Satellite / Cable, Television, DVD Player, Parking

Key West Enjoy More Privacy in a Truman Annex End Unit Townhome

  • 2 BR/1 BA, 1 half bath Townhome (sleeps 5)
    $200 - $425/nt
    $1,400 - $2,800/wk
    $4,200 - $7,800/month
    per property, Village, Communal Pool, Lawn / Garden, Balcony, Air Conditioning, Internet, Satellite / Cable, Television

Key West Charming Yacht Located in Exclusive, Beautiful Key West Harbour Yacht Club

  • 2 BR/1 BA Yacht (sleeps 4)
    $190 - $225/nt
    per property, accept credit card, Beach, Waterfront, Communal Pool, Sauna, Fitness Room / Equipment, Air Conditioning, Satellite / Cable, Television

Key West "Royal Oasis" - Beautiful 2/2 Monthly Rental W/ Heated Pool.

  • 2 BR/2 BA House (sleeps 4)
    $5,000 - $8,000/month
    per property, Private Pool, Air Conditioning, Internet

Key West Gorgeous 3 Bed 3 Bath w/ Brand New Pool.

  • 3 BR/3 BA House (sleeps 6)
    $5,133 - $7,700/month
    per property, pets considered, Private Pool, Air Conditioning, Internet, Satellite / Cable

Key West (New Addition) Luxurious 5 Bedroom Mansion w/ Private Beach!

  • 5 BR/5 BA House (sleeps 14)
    $18,667 - $25,667/month
    per property, pets considered, Hot Tub, Beach, Private Pool, Balcony, Air Conditioning, Internet, Satellite / Cable

Key West Windward Isle

  • 2 BR/1 BA House (sleeps 6)
    $258 - $448/nt
    $3,136/wk
    per property, pets considered, Hot Tub, Air Conditioning, Internet, Satellite / Cable

Key West Villa Azul - Monthly Rental

  • 3 BR/3 BA House (sleeps 6)
    $6,067 - $9,100/month
    per property, pets considered, Air Conditioning, Internet, Satellite / Cable, DVD Player

Key West AFFORDABLE NIGHTLY RENTAL 1 BLOCK FROM DUVAL ST! 'TRUMAN EFFICIENCY' WELL KEP

  • Studio/1 BA Condo (sleeps 2)
    $138 - $268/nt
    $1,876/wk
    per property, pets considered, Air Conditioning, Internet, Satellite / Cable

Key West Tradewinds Sleeps up to 12

  • 4 BR/2 BA House (sleeps 12)
    $468 - $828/nt
    $5,796/wk
    per property, pets considered, Hot Tub, Air Conditioning, Internet, Satellite / Cable

Key West Tobago

  • 3 BR/3 BA House (sleeps 6)
    $4,667 - $6,767/month
    per property, pets considered, Hot Tub, Communal Pool, Air Conditioning, Internet, Satellite / Cable

Key West Shipyard Perch - Weekly or Monthly (Truman Annex)

  • 2 BR/2 BA Condo (sleeps 4)
    $1,400 - $2,400/wk
    $3,750 - $5,500/month
    per property, Communal Pool, Balcony, Air Conditioning, Internet

Key West Shipyard - Weekly Or Monthly (Truman Annex)

  • 2 BR/1 BA Condo (sleeps 4)
    $1,300 - $2,100/wk
    $3,500 - $6,000/month
    per property, Communal Pool, Air Conditioning, Internet, Satellite / Cable, DVD Player

Key West Seabreeze - Luxurious 2/1 Condo in Old Town Key West. A Parrot Heads Paradise

  • 2 BR/1 BA Condo (sleeps 4)
    $208 - $348/nt
    $2,436/wk
    per property, pets considered, Balcony, Air Conditioning, Internet, Satellite / Cable
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