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 Poolside Paradise

  • 3 BR/2 BA House (sleeps 10)
    $408 - $768/nt
    $5,376/wk
    per property, pets considered, Balcony, Air Conditioning, Internet, Satellite / Cable

Key West Luxury on Garrison Bight: 3 BR/3.5 BA Waterfront Home Sleeps 8

  • 3 BR/3 BA, 1 half bath House (sleeps 8)
    $595 - $795/nt
    per property, accept credit card, pets considered, Near The Ocean, Town, Waterfront, Private Pool, Balcony, Internet, Satellite / Cable, Television

Key West The Cristol Condo - Classic Key West Oceanfront Charm

  • 4 BR/4 BA Condo (sleeps 8)
    $849/nt
    per property, pets considered, Waterfront, Communal Pool, Balcony, Air Conditioning, Internet, Satellite / Cable, Television

Key West KEY WEST HOT SPOT! 'ALMOST SOUTHERNMOST' CLOSE TO SOUTHERNMOST POINT - SLEEP

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

Key West Egret Cottage: 1 BR / 1.0 BA house in Key West, Sleeps 4

  • 1 BR/1 BA House (sleeps 4)
    $190 - $384/nt
    $1,050 - $2,320/wk
    per property, Communal Pool, Air Conditioning, Internet, Television, DVD Player

Key West Tropical Dreaming: 2 BR / 2.5 BA house in Key West, Sleeps 6

  • 2 BR/2 BA, 1 half bath House (sleeps 6)
    $340 - $681/nt
    $2,100 - $4,350/wk
    per property, pets considered, Private Pool, Air Conditioning, Internet, Television, DVD Player, Parking

Key West Leeward Isle Key West Retreat

  • 2 BR/2 BA Condo (sleeps 4)
    $265 - $471/nt
    $1,575 - $2,900/wk
    per property, Communal Pool, Air Conditioning, Internet, Television, Parking

Key West Linger Longer: 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, DVD Player, Parking

Key West Key West Casa: 3 BR / 2.0 BA condo in Key West, Sleeps 6

  • 3 BR/2 BA Condo (sleeps 6)
    $2,000 - $5,075/wk
    per property, Communal Pool, Air Conditioning, Internet, Television, DVD Player, Parking

Key West Coral Suite: 2 BR / 3.0 BA condo in Key West, Sleeps 6

  • 2 BR/3 BA Condo (sleeps 6)
    $150 - $337/nt
    $900 - $2,093/wk
    per property, pets considered, Communal Pool, Air Conditioning, Television, Parking

Key West Key West Found: 2 BR / 2.5 BA condo in KEY WEST, Sleeps 6

  • 2 BR/2 BA, 1 half bath Condo (sleeps 6)
    $1,650 - $3,552/wk
    per property, Communal Pool, Air Conditioning, Internet, Television, DVD Player, Parking

Key West Coral Garden: 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, Communal Pool, Air Conditioning, Internet, Television, DVD Player, Parking

Key West Lavender Jungle: 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, DVD Player, Parking

Key West Luxurious Garden Home Paradise with Pool in Midtown Key West

  • 2 BR/1 BA House (sleeps 6)
    $127 - $173/nt
    $3,547 - $4,853/month
    per property, accept credit card, pets considered, Beach, Near The Ocean, Private Pool, Lawn / Garden, Air Conditioning, Internet, Satellite / Cable

Key West WATERFRONT Penthouse, Key West between MM 10 just 5 min to KW

  • 2 BR/1 BA Condo (sleeps 4)
    $150/nt
    $850/wk
    $3,294/month
    per property, accept credit card, Near The Ocean, Waterfront, terrace, Balcony, Air Conditioning, Internet, Satellite / Cable, Television

Key West Casa Bonita - Beautiful 2/2.5 Condo w/ Pool on Duval Street! Sleeps up to 7!

  • 2 BR/2 BA, 1 half bath Condo (sleeps 7)
    $258 - $458/nt
    $3,206/wk
    per property, pets considered, Communal Pool, Balcony, Air Conditioning, Internet, Satellite / Cable

Key West Luxury Waterfront at the Galleon Resort in Old Town

  • 2 BR/2 BA Condo (sleeps 8)
    $450 - $625/nt
    $2,750 - $3,750/wk
    per property, accept credit card, Hot Tub, limited accessibility, Resort, Waterfront, Communal Pool, Sauna, Balcony, Fitness Room / Equipment

Key West Providence Suite - Monthly Rental

  • 1 BR/1 BA Townhome (sleeps 6)
    $2,333 - $4,433/month
    per property, pets considered, Communal Pool, Air Conditioning, Internet, Satellite / Cable, DVD Player

Key West Atlantic Ocean View

  • 2 BR/2 BA Condo (sleeps 6)
    $288 - $438/nt
    $3,066/wk
    per property, Hot Tub, Beach, Communal Pool, Balcony, Air Conditioning, Internet, Satellite / Cable, DVD Player

Key West Almost Southernmost Too

  • 3 BR/2 BA, 1 half bath House (sleeps 8)
    $378 - $668/nt
    $4,676/wk
    per property, pets considered, Private Pool, Balcony, Air Conditioning, Internet, DVD Player

Key West Almost Southernmost Retreat - Sleeps up to 16!

  • 5 BR/3 BA, 1 half bath House (sleeps 16)
    $638 - $1,248/nt
    $8,736/wk
    per property, pets considered, Hot Tub, Private Pool, Balcony, Air Conditioning, Internet, Satellite / Cable, DVD Player

Key West Verde Suite

  • 1 BR/1 BA Condo (sleeps 4)
    $178 - $318/nt
    $2,226/wk
    per property, pets considered, Communal Pool, Air Conditioning, Internet, Satellite / Cable

Key West Tres Flores - Sleeps up to 10!

  • 3 BR/3 BA Condo (sleeps 10)
    $378 - $768/nt
    $5,376/wk
    per property, Balcony, Air Conditioning, Internet, Satellite / Cable, DVD Player

Key West Starr's Suite

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

Key West Spa on Duval Gorgeous 2-Br 2.5-Ba Condo w/ Pvt Hot Tub! Located on Duval Stre

  • 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 Osprey’s Nest

  • 1 BR/1 BA Condo (sleeps 4)
    $178 - $328/nt
    $1,386 - $2,296/wk
    per property, pets considered, Hot Tub, Communal Pool, Balcony, Air Conditioning, Internet, Satellite / Cable

Key West A KEY WEST HOT SPOT! 'McCartney's Manor' PRIVATE HOT TUB!

  • Studio/1 BA Cottage (sleeps 2)
    $198 - $348/nt
    $2,436/wk
    per property, pets considered, Hot Tub, Communal Pool, Balcony, Air Conditioning, Internet, Satellite / Cable, DVD Player

Key West Lennon's Lodge

  • 2 BR/1 BA Cottage (sleeps 6)
    $298 - $518/nt
    $3,626/wk
    per property, pets considered, Hot Tub, Communal Pool, Air Conditioning, Internet, Satellite / Cable, DVD Player

Key West Little Havana Suite

  • 1 BR/1 BA, 1 half bath Townhome (sleeps 4)
    $188 - $328/nt
    $2,296/wk
    per property, pets considered, Communal Pool, Air Conditioning, Internet, Satellite / Cable

Key West Lazy Lane - Weekly or Monthly (Truman Annex)

  • 2 BR/1 BA Condo (sleeps 4)
    $1,300 - $2,400/wk
    $3,750 - $6,500/month
    per property, pets considered, Communal Pool, Balcony, Air Conditioning, Internet, Satellite / Cable

Key West LUXURY & LOCATION! A GREAT GETAWAY SPOT FOR TWO :) 'JASMINE SUITE'

  • 1 BR/1 BA Condo (sleeps 4)
    $148 - $278/nt
    $1,946/wk
    per property, Balcony, Air Conditioning, Internet, Satellite / Cable

Key West Duval Square Penthouse

  • 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 Casa Caribe

  • 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 'A KEY ESCAPE' - LOCATION & LUXURY - 1 BLOCK FROM DUVAL - SLEEPS UP TO 8

  • 3 BR/2 BA, 1 half bath House (sleeps 8)
    $408 - $768/nt
    $5,376/wk
    per property, pets considered, Private Pool, Balcony, Air Conditioning, Internet, Satellite / Cable, DVD Player

Key West Carpe Diem- a tropical Conch Cottage in old town Key West -

  • 2 BR/2 BA Cottage (sleeps 6)
    $2,707 - $6,067/month
    per property, accept credit card, pets considered, Beach, Near The Ocean, Town, Lawn / Garden, terrace, Balcony, Air Conditioning, Internet

Key West Tropical Retreat

  • 3 BR/3 BA, 1 half bath House (sleeps 8)
    $408 - $768/nt
    $5,376/wk
    per property, pets considered, Air Conditioning, Internet, Satellite / Cable

Key West Coral Hammock - Beautiful Poolside Home (28)

  • 3 BR/3 BA House (sleeps 6)
    $275 - $350/nt
    $1,500 - $2,000/wk
    $5,500 - $7,000/month
    per property, accept credit card, Communal Pool, Balcony, Fitness Room / Equipment, Air Conditioning, Internet, Satellite / Cable, DVD Player

Key West Special April 2014 Monthly Rate - Key West Ocean Side Luxury On Smather's Beach

  • 2 BR/2 BA Condo (sleeps 6)
    $3,547 - $6,300/month
    per property, pets considered, wheelchair accessible, Beach, Near The Ocean, Communal Pool, Sauna, Tennis Court, Lawn / Garden, Balcony

Key West Luxury Spacious Townhouse overlooking Pool w/ water view & 2 Bikes

  • 1 BR/1 BA Townhome (sleeps 4)
    $185 - $270/nt
    $1,166 - $1,345/wk
    per property, accept credit card, Hot Tub, Resort, Communal Pool, Air Conditioning, Internet, Satellite / Cable, Television

Key West Truman Annex: Southern Palm Self Catering Spacious town home with large deck

  • 2 BR/2 BA, 1 half bath Townhome (sleeps 6)
    $257 - $471/nt
    $1,800 - $3,300/wk
    $5,400/month
    per property, Near The Ocean, Communal Pool, Lawn / Garden, terrace, Balcony, Air Conditioning, Internet, Satellite / Cable

Key West Sunset Lake@Key West Golf Club 3BR/3FullBA ~ 2 Master Suites ~ CREDIT CARDS ACCP

  • 3 BR/3 BA Townhome (sleeps 6)
    $3,200/month
    per property, accept credit card, pets considered, Beach, Lake, Near The Ocean, Resort, Communal Pool, Balcony, Fitness Room / Equipment, Air Conditioning, Internet

Key West Simonton Studio, an Old Town get-away for 2. New Pricing

  • 1 BA Studio (sleeps 2)
    $120 - $250/nt
    $780 - $1,600/wk
    per property, accept credit card, Near The Ocean, Air Conditioning, Internet, Satellite / Cable, Television, DVD Player

Key West Old Town location close to beach, shops & more

  • 2 BR/1 BA Condo (sleeps 4)
    $1,125 - $2,100/wk
    $7,500/month
    per property, accept credit card, Downtown, Near The Ocean, Communal Pool, Air Conditioning, Internet, Satellite / Cable, Television, DVD Player

Key West 4 Palms: 2 BR / 2.0 BA condo in Key West, Sleeps 6

  • 2 BR/2 BA Condo (sleeps 6)
    $220 - $381/nt
    $1,250 - $2,406/wk
    per property, Hot Tub, Near The Ocean, Communal Pool, Air Conditioning, Internet, Television, DVD Player, Parking

Key West Caribbean Suite

  • 1 BR/1 BA, 1 half bath Townhome (sleeps 4)
    $198 - $338/nt
    $2,366/wk
    per property, pets considered, Communal Pool, Air Conditioning, Internet, Satellite / Cable, DVD Player

Key West Islands In the Stream - Papa`s Hideaway Historic Inn - Studio (First Floor)

  • Studio/1 BA House (sleeps 4)
    $139 - $249/nt
    $1,743/wk
    per property, Communal Pool, Balcony, Air Conditioning, Internet, Satellite / Cable

Key West Torrents of Spring - Papa`s Hideaway Historic Inn - Deluxe Studio (2nd Floor)

  • Studio/1 BA House (sleeps 4)
    $149 - $259/nt
    $1,813/wk
    per property, Communal Pool, Balcony, Air Conditioning, Internet, Satellite / Cable

Key West Abbey Road - Great for Big Parties! 4 Units w/ 4 PVT Hot Tubs Key West Favori

  • 5 BR/4 BA Cottage (sleeps 12)
    $778 - $1,328/nt
    $9,296/wk
    per property, pets considered, Hot Tub, Communal Pool, Balcony, Air Conditioning, Internet, Satellite / Cable, DVD Player

Key West Spring & Summer Big Discounts, Great Reviews, Perfect Key West Condo

  • 2 BR/2 BA, 1 half bath Condo (sleeps 5)
    $1,750 - $2,751/wk
    $6,750 - $9,450/month
    per property, accept credit card, Beach, Downtown, Near The Ocean, Town, Communal Pool, Lawn / Garden, Balcony, Air Conditioning, Internet, Satellite / Cable
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