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 8

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SPECIAL OFFER! Summer Special - $1,000.00/Week July 1 - October 18

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
    $1,000 - $1,500/wk
    $3,500/month
    per property, Near The Ocean, Communal Pool, Balcony, Fitness Room / Equipment, Air Conditioning, Internet, Satellite / Cable, Television
SPECIAL OFFER! June 2013 - Month at 20% SAVINGS June 3 - August 29

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

  • 2 BR/1 BA Cottage (sleeps 4)
    $3,000 - $5,000/month
    per property, accept credit card, Beach, Downtown, Lawn / Garden, pets considered, Air Conditioning, Internet, Satellite / Cable, Television

Key West Exquisite 3BR Home on Shark Key - Enjoy the Best Tropical Sunsets of Your Life!

  • 3 BR/3 BA, 1 half bath House (sleeps 8)
    $2,250/wk
    per property, Beach, Lawn / Garden, Balcony, Internet, Television

Key West LOOK! Vacation on a Yacht in First-Class Marina!

  • 2 BR/2 BA Boat (sleeps 4)
    $300 - $350/nt
    $2,000/wk
    per property, accept credit card, Communal Pool, Jacuzzi, Balcony, Fitness Room / Equipment, Air Conditioning, Internet, Television

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

  • 2 BR/1 BA, 1 half bath Townhome (sleeps 5) Village, Communal Pool, Lawn / Garden, Balcony, Air Conditioning, Internet, Satellite / Cable, Television

Key West 'SUZY'S PARROT PERCH @ SOUTHERNMOST': Cozy 2BR/1BA Suite Near Duval...

  • 2 BR/1 BA Apartment (sleeps 4)
    $230 - $425/nt
    $1,150 - $2,100/wk
    $3,900 - $8,000/month
    per property, accept credit card, Downtown, Near The Ocean, Balcony, pets considered, Air Conditioning, Internet, Satellite / Cable, Television

Key West 'SOUTHERNMOST COMFORT @ CASA EAST': Stunning 4BR/4.5BA Home w/ Cottage & Pool...

  • 4 BR/4 BA, 1 half bath House (sleeps 8)
    $9,000 - $17,000/month
    per property, accept credit card, Near The Ocean, Resort, Jacuzzi, Lawn / Garden, terrace, Balcony, Air Conditioning, Internet

Key West Attitude Key West At the Beach

  • 1 BR Condo (sleeps 4) accept credit card, wheelchair accessible, Beach, Downtown, Near The Ocean, Resort, Town, Waterfront, Communal Pool, Sauna, Lawn / Garden, Balcony, Air Conditioning

Key West Key West Condo in Truman Annex with Whirlpool Tub, 2 Bikes, & Access to Pool!

  • 2 BR Condo (sleeps 4) accept credit card, Beach, Downtown, Communal Pool, Balcony, Air Conditioning, Internet, Satellite / Cable, Television

Key West The Victoria House

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

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

Key West Coral Caribe

  • 2 BR/2 BA, 1 half bath Condo (sleeps 6)
    $150 - $306/nt
    $900 - $1,906/wk
    per property, Private Pool, Communal Pool, pets considered, Air Conditioning, Internet, DVD Player, Parking

Key West Key West Crown Jewel

  • 2 BR/2 BA Condo (sleeps 6)
    $345 - $531/nt
    $2,145 - $3,368/wk
    per property, Communal Pool, Air Conditioning, Internet, Television, DVD Player, Parking

Key West Ocean Perch , Dock 80'Heated Pool Deep Channel Tennis 15 min Key West

  • 2 BR/2 BA House (sleeps 6)
    $975 - $1,600/wk
    per property, accept credit card, Resort, Communal Pool, Tennis Court, Balcony, Air Conditioning, Internet, Satellite / Cable

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

  • 3 BR/3 BA Condo (sleeps 6)
    $2,500 - $5,000/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 vacation townhouse rental in the Truman Annex

  • 2 BR/2 BA, 1 half bath Townhome (sleeps 6)
    $1,400 - $2,750/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 The Cristol Condo - Classic Key West Oceanfront Charm

  • 4 BR/4 BA Condo (sleeps 8)
    $4,989/wk
    per property, Waterfront, Communal Pool, Balcony, pets considered, Air Conditioning, Internet, Satellite / Cable, Television

Key West Location, Location, Location! Ocean View, Lagoon Beach Front

  • 3 BR/2 BA House Boat (sleeps 10) accept credit card, Beach, Downtown, Near The Ocean, Resort, Waterfront, Communal Pool, Jacuzzi, Sauna, Balcony, Air Conditioning, Internet

Key West HGTV Featured Home - Boaters Paradise! Waterfront Key West Home

  • 3 BR/2 BA House (sleeps 6)
    $6,200/month
    per property, Near The Ocean, Waterfront, Jacuzzi, Lawn / Garden, terrace, Balcony, pets considered, Air Conditioning, Internet

Key West Villa Nomade, Elegant Truman Annex condo in Old Town

  • 2 BR/1 BA Condo (sleeps 4)
    $1,200 - $1,500/wk
    per property, accept credit card, Near The Ocean, Town, Communal Pool, Lawn / Garden, Air Conditioning, Satellite / Cable, Television, DVD Player
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Key West Quiet, elegant, Key West Condo close to the Ocean

  • 2 BR/2 BA Condo (sleeps 6)
    $175 - $225/nt
    $1,225 - $1,575/wk
    per property, accept credit card, wheelchair accessible, Beach, Near The Ocean, Communal Pool, Tennis Court, Balcony, pets considered, Fitness Room / Equipment

Key West Ocean Suite at the Galleon Resort

  • 2 BR/2 BA Condo (sleeps 8) accept credit card, Downtown, Waterfront, Communal Pool, Jacuzzi, Balcony, 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) accept credit card, Near The Ocean, Waterfront, terrace, Balcony, Air Conditioning, Internet, Satellite / Cable, Television

Key West Sunshine Luxury Suite with 2 Free Bikes & Garage

  • 2 BR/2 BA Condo (sleeps 6)
    $1,300/wk
    per property, accept credit card, Near The Ocean, Resort, Communal Pool, Jacuzzi, Tennis Court, Balcony, pets considered, Fitness Room / Equipment

Key West Charming, Romantic, Funky, Cozy, Unique, Beautiful, Island Charm, Beach, Ocean

  • 1 BR/1 BA Bungalow (sleeps 2) accept credit card, Tennis Court, Lawn / Garden, Balcony, Air Conditioning, Internet, Satellite / Cable, Television

Key West Coral Hammock - Tropical Paradise Home (15)

  • 3 BR/3 BA Townhome (sleeps 6) Beach, Near The Ocean, Communal Pool, Balcony, Fitness Room / Equipment, Air Conditioning, Internet, Satellite / Cable, Television

Key West Coral Hammock - Beautiful Poolside Home (28)

  • 3 BR/3 BA House (sleeps 6)
    $250 - $350/nt
    $1,400 - $2,000/wk
    $4,200 - $7,000/month
    per property, accept credit card, Communal Pool, Balcony, pets considered, Fitness Room / Equipment, Air Conditioning, Internet, Satellite / Cable

Key West My Condo by the Beach with Ocean View

  • 1 BR/1 BA Condo (sleeps 4)
    $975 - $1,550/wk
    per property, accept credit card, Beach, Town, Communal Pool, Balcony, Air Conditioning, Internet, Satellite / Cable, Television

Key West Beach house exclusive private resort island 500 yards from heart of Key West

  • 3 BR House (sleeps 6)
    $20,000 - $25,000/month
    per property, accept credit card, Beach, Resort, Private Pool, Tennis Court, Air Conditioning, Internet, Satellite / Cable, Television

Key West Osprey

  • 1 BR/1 BA Condo (sleeps 2)
    $130 - $321/nt
    $650 - $1,823/wk
    per property, Communal Pool, Air Conditioning, Internet, Television, DVD Player
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Key West Key West Ginger House

  • 2 BR/2 BA House (sleeps 6)
    $210 - $413/nt
    $1,200 - $2,465/wk
    per property, pets considered, Air Conditioning, Internet, Television, DVD Player, Parking

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)
    $495 - $695/nt
    per property, accept credit card, Near The Ocean, Town, Waterfront, Private Pool, Balcony, pets considered, Internet, Satellite / Cable, Television

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

  • 2 BR/2 BA Condo (sleeps 6)
    $265 - $495/nt
    $1,395 - $2,850/wk
    per property, accept credit card, wheelchair accessible, Beach, Near The Ocean, Resort, Waterfront, Private Pool, Jacuzzi, Sauna, Tennis Court, terrace

Key West 'VILLA BAHAMA @ THE FOUNDRY': Luxury 2BR/2.5BA Townhome in Truman Annex...

  • 2 BR/2 BA, 1 half bath Villa (sleeps 6)
    $1,950 - $3,500/wk
    $6,600 - $11,500/month
    per property, accept credit card, Downtown, Near The Ocean, Resort, Town, Village, Communal Pool, Lawn / Garden, terrace, Balcony, Air Conditioning, Internet

Key West 'HEAVENLY ZEN @ THE SEAPORT': Lavish 4BR/3BA Old Town Home + Pool....

  • 4 BR/3 BA House (sleeps 8)
    $11,000 - $19,000/month
    per property, accept credit card, Downtown, Near The Ocean, Resort, Private Pool, Jacuzzi, Lawn / Garden, terrace, Balcony, Air Conditioning

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

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

Key West New Home In Old Town

  • 4 BR/4 BA House (sleeps 8) limited accessibility, Beach, Downtown, Near The Ocean, Waterfront, Private Pool, pets considered, Air Conditioning, Internet, Television, DVD Player

Key West 'CASA LOUISA @ UPPER DUVAL': Historic Conch Cottage & Pool 1/2 Block off Duval..

  • 3 BR/2 BA Cottage (sleeps 8)
    $400 - $750/nt
    $2,400 - $4,000/wk
    $8,000 - $15,000/month
    per property, accept credit card, Town, Village, Private Pool, pets considered, Air Conditioning, Internet, Satellite / Cable, Television

Key West Bahama Dreaming

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

Key West Key West Found

  • 2 BR/2 BA, 1 half bath Condo (sleeps 6)
    $1,600 - $3,407/wk
    per property, Communal Pool, Air Conditioning, Internet, Television, DVD Player, Parking
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Key West Crowner's Jewel

  • 2 BR/2 BA, 1 half bath Condo (sleeps 6)
    $1,500 - $3,153/wk
    per property, Communal Pool, Air Conditioning, Internet, DVD Player, Parking

Key West Truman Annex: The Plantation SELF CATERING beautifully landscaped rear patio

  • 3 BR/3 BA Townhome (sleeps 6)
    $2,500 - $4,560/wk
    $7,500 - $10,500/month
    per property, Beach, Near The Ocean, Communal Pool, Lawn / Garden, Balcony, Air Conditioning, Internet, Satellite / Cable, Television

Key West Casa Marina Oasis

  • 2 BR/2 BA House (sleeps 6)
    $4,000 - $7,000/month
    per property, Beach, Downtown, Near The Ocean, Private Pool, Air Conditioning, Internet, Satellite / Cable, Television, DVD Player, Parking

Key West Private Luxury in Prestigious Casa Marina Neighborhood

  • 3 BR/3 BA, 1 half bath House (sleeps 7)
    $3,500 - $8,800/month
    per property, Downtown, Near The Ocean, Private Pool, Lawn / Garden, Balcony, Air Conditioning, Internet, Satellite / Cable, Television

Key West William Skelton -- Location, location, location -- in Old Town Key West!

  • 6 BR/4 BA House (sleeps 16)
    $650 - $1,200/nt
    per property, accept credit card, Downtown, Near The Ocean, Lawn / Garden, Balcony, Air Conditioning, Internet, Satellite / Cable, Television

Key West Oceanfront Acre Heated Private Pool Sandy Area Dock 15 Min Key West

  • 3 BR/2 BA House (sleeps 10)
    $1,800 - $2,950/wk
    per property, accept credit card, Beach, Waterfront, Private Pool, Lawn / Garden, terrace, Balcony, Air Conditioning, Internet

Key West Tiki Beach Too, Charming Townhome, Old Town, Pool Access, great porch!

  • 2 BR/1 BA Townhome (sleeps 6) wheelchair accessible, Beach, Downtown, Near The Ocean, Communal Pool, Lawn / Garden, pets considered, Air Conditioning, Internet, Satellite / Cable

Key West Paradise Manor with private pool available June 2013

  • 4 BR/2 BA House (sleeps 9)
    $100 - $400/nt
    $1,790 - $1,990/wk
    $3,490 - $4,450/month
    per property, accept credit card, Beach, Near The Ocean, Private Pool, Lawn / Garden, Air Conditioning, Internet, Satellite / Cable, Television

Key West Full Month Discounts Now Available in Truman Annex, Key West

  • 2 BR/2 BA, 1 half bath Condo (sleeps 5) accept credit card, Beach, Downtown, Near The Ocean, Town, Communal Pool, Lawn / Garden, Balcony, Air Conditioning, Internet, Satellite / Cable

Key West Spa On Duval

  • 2 BR/2 BA, 1 half bath Condo (sleeps 6)
    $240 - $456/nt
    $1,400 - $2,900/wk
    per property, Communal Pool, Air Conditioning, DVD Player, Parking
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