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
SPECIAL OFFER! Spring Promotion May 28 - June 20

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 Galleon Resort Efficiency Historic District

  • 1 BR/1 BA Condo (sleeps 2)
    $219 - $299/nt
    $1,573 - $2,093/wk
    $6,730 - $7,770/month
    per property, accept credit card, Hot Tub, Near The Ocean, Waterfront, Communal Pool, Balcony, Air Conditioning, Internet, Satellite / Cable

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 'SOUTHERN STAR @ THE SEAPORT'' Renovated Historic 3BR/3BA Home with Pool...

  • 3 BR/3 BA House (sleeps 6)
    $7,187 - $16,800/month
    per property, Downtown, Near The Ocean, Village, Waterfront, Private Pool, Lawn / Garden, Balcony, Air Conditioning, Internet, Satellite / Cable, Television

Key West 'CASA FELIZ @ THE SEAPORT': Lushly Furnished 3BR/3.5BA Private Home + Pool...

  • 3 BR/3 BA House (sleeps 8)
    $6,160 - $14,933/month
    per property, accept credit card, Downtown, Near The Ocean, Village, Private Pool, Jacuzzi, Lawn / Garden, terrace, Air Conditioning, Internet

Key West Pelican Landing Dominica Retreat

  • 2 BR/2 BA Condo (sleeps 8)
    $300 - $450/nt
    $2,100 - $3,150/wk
    $9,000/month
    per property, pets considered, Communal Pool, Balcony, Air Conditioning, Internet, Satellite / Cable, DVD Player

Key West Pelican Landing Bonaire Retreat

  • 2 BR/2 BA Condo (sleeps 8)
    $300 - $450/nt
    $2,100 - $3,150/wk
    $9,000/month
    per property, pets considered, Communal Pool, Balcony, Air Conditioning, Internet, Satellite / Cable, DVD Player

Key West Pelican Landing Abaco Retreat

  • 2 BR/2 BA Condo (sleeps 8)
    $300 - $450/nt
    $2,100 - $3,150/wk
    $9,000/month
    per property, pets considered, Communal Pool, Balcony, Air Conditioning, Internet, Satellite / Cable

Key West Tiki Beach Too, Charming Townhome, OldTown, Pool Access, Budget, Hideaway Porch!

  • 2 BR/1 BA Townhome (sleeps 6)
    $1,346 - $1,946/wk
    $2,995 - $4,865/month
    per property, pets considered, wheelchair accessible, Beach, Downtown, Near The Ocean, Communal Pool, Lawn / Garden, Air Conditioning, Internet, Satellite / Cable

Key West Pelican Landing Florida Retreat

  • 2 BR/2 BA Condo (sleeps 8)
    $300 - $450/nt
    $2,100 - $3,150/wk
    $9,000/month
    per property, pets considered, Communal Pool, Balcony, Air Conditioning, Internet, Satellite / Cable

Key West Coral Hammock - Tropical Paradise Home (15)

  • 3 BR/3 BA Townhome (sleeps 6)
    $275 - $350/nt
    $1,500 - $2,000/wk
    $5,500 - $7,000/month
    per property, Beach, Near The Ocean, Communal Pool, Balcony, Fitness Room / Equipment, Air Conditioning, Internet, Satellite / Cable, Television

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 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 'CONCH CASA GRANDE @ THE ANNEX': Enormous 7BR/7BA in Truman Annex...

  • 7 BR/7 BA House (sleeps 12)
    $9,500 - $13,500/wk
    $30,000 - $49,000/month
    per property, accept credit card, pets considered, Downtown, Near The Ocean, Village, Private Pool, Balcony, Air Conditioning, Internet, Satellite / Cable

Key West 'PROMENADE TO PARADISE @ THE ANNEX': Spacious 2BR/2BA Waterfront Condo...

  • 2 BR/2 BA Condo (sleeps 6)
    $2,650 - $4,800/wk
    $8,900 - $16,500/month
    per property, accept credit card, pets considered, Communal Pool, Balcony, Air Conditioning, Internet, Satellite / Cable, Television

Key West 'CASA, SUITE CASA @ CASA MARINA': Lavish New Home W/ 4 Suites + Pool...

  • 4 BR/5 BA House (sleeps 10)
    $8,400 - $18,667/month
    per property, accept credit card, Hot Tub, Beach, Downtown, Near The Ocean, Town, Private Pool, Lawn / Garden, Balcony, Air Conditioning, Internet

Key West 'PORTSIDE MANSION @ THE SEAPORT': Magnificent 3-Building Compound + Large Pool..

  • 6 BR/6 BA, 1 half bath Estate (sleeps 12)
    $17,733 - $27,067/month
    per property, accept credit card, pets considered, Downtown, Near The Ocean, Village, Private Pool, Jacuzzi, Lawn / Garden, terrace, Balcony

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 "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 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 (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 (New) Gorgeous 2 Bedroom Two Bathroom In Old Town Key West. Newly Renovated!

  • 2 BR/3 BA House (sleeps 4)
    $4,200 - $7,000/month
    per property, 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 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 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 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 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 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 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 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 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 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 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 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 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 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 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 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 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 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 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 LUXURY & LOCATION! A GREAT GETAWAY SPOT FOR TWO :) 'ORCHID SUITE'

  • 1 BR/1 BA Condo (sleeps 4)
    $148 - $278/nt
    $1,946/wk
    per property, 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 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
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