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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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 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 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 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 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 Seashore At The 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, Balcony, 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

Key West Secret Garden - 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 Romantic Retreat

  • 1 BR/1 BA Cottage (sleeps 2)
    $178 - $318/nt
    $2,226/wk
    per property, pets considered, Hot Tub, Communal Pool, Air Conditioning, Internet, Satellite / Cable, DVD Player

Key West Playa Royale - Monthly Rental

  • 2 BR/2 BA Condo (sleeps 4)
    $3,267 - $5,367/month
    per property, Hot Tub, Beach, Communal Pool, Sauna, Balcony, Air Conditioning, Internet, Satellite / Cable

Key West Pinder House - Monthly Rental

  • 2 BR/2 BA House (sleeps 4)
    $6,533 - $6,767/month
    per property, pets considered, Hot Tub, Balcony, Air Conditioning, Satellite / Cable

Key West Paradise Suite - Monthly Rental

  • 1 BR/1 BA, 1 half bath Townhome (sleeps 4)
    $2,333 - $4,433/month
    per property, pets considered, Communal Pool, Air Conditioning, Internet, Satellite / Cable

Key West Passover Cottage

  • 2 BR/2 BA House (sleeps 6)
    $378 - $708/nt
    $4,956/wk
    per property, pets considered, Air Conditioning, Internet, Satellite / Cable

Key West Paradise Palms - Monthly Rental

  • 2 BR/2 BA House (sleeps 6)
    $3,733 - $5,833/month
    per property, Balcony, Air Conditioning, Internet, Satellite / Cable

Key West Palm Isle

  • 1 BR/1 BA Condo (sleeps 4)
    $178 - $328/nt
    $2,296/wk
    per property, pets considered

Key West Palm Gardens - Great for Groups!

  • 4 BR/4 BA Condo (sleeps 16)
    $528 - $888/nt
    $6,216/wk
    per property, pets considered, Hot Tub, Balcony, Air Conditioning, Internet, Satellite / Cable

Key West Old Town Garden Villas - Sleeps up to 20!

  • 5 BR/7 BA Townhome (sleeps 20)
    $878 - $1,448/nt
    $10,136/wk
    per property, pets considered, Communal Pool, Balcony, Air Conditioning, Internet, Satellite / Cable

Key West Monroe Efficiency

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

Key West AFFORDABLE NIGHTLY RENTAL 1 BLOCK FROM DUVAL ST! 'MALLORY EFFICIENCY' WELL KE

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

Key West Leeward Isle - Half a block from Duval!

  • 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 Island Rendezvous - Monthly Rental

  • 2 BR/1 BA House (sleeps 4)
    $4,200 - $7,700/month
    per property, Air Conditioning, Internet, Satellite / Cable

Key West Howe Street Hideaway - Monthly Rental

  • 2 BR/2 BA House (sleeps 6)
    $2,333 - $4,900/month
    per property, Air Conditioning, Internet, Satellite / Cable

Key West Havana Hideaway

  • 2 BR/2 BA, 1 half bath Condo (sleeps 6)
    $268 - $468/nt
    $3,276/wk
    per property, pets considered, Hot Tub, Communal Pool, Balcony, Air Conditioning, Internet, Satellite / Cable

Key West Fleming O House - 2Br 1Bath House by Duval Street! A Favorite! Sleeps up to 6

  • 2 BR/1 BA House (sleeps 6)
    $228 - $438/nt
    $3,066/wk
    per property, pets considered, Balcony, Air Conditioning, Internet, Satellite / Cable

Key West Fishtail Hideaway - Monthly Rental

  • 1 BR/2 BA House (sleeps 4)
    $2,333 - $4,433/month
    per property, Private Pool, Balcony, Air Conditioning, Internet, Satellite / Cable
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