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 10

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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 'OLD TOWN OASIS @ TRUMAN ANNEX': Luxurious 2BR/2BA Condo + Oceanside Pool...

  • 2 BR/2 BA Condo (sleeps 6)
    $2,400 - $3,950/wk
    $8,750 - $14,500/month
    per property, accept credit card, wheelchair accessible, Downtown, Waterfront, Communal Pool, Balcony, Air Conditioning, Internet, Satellite / Cable

Key West 'THE CONTENTED CRANE @ OLD TOWN': Pristine 3BR/3.5BA Home + Private Pool...

  • 3 BR/3 BA, 1 half bath Townhome (sleeps 8)
    $700 - $1,050/nt
    $3,850 - $5,950/wk
    $13,000 - $20,500/month
    per property, pets considered, wheelchair accessible, Downtown, Village, Private Pool, Balcony, Air Conditioning, Internet, Satellite / Cable

Key West 'COOL BREEZE @ THE ANNEX': Meticulously Furnished 2BR/2.5BA Old Town Villa...

  • 2 BR/2 BA, 1 half bath Villa (sleeps 6)
    $2,000 - $3,750/wk
    $6,600 - $13,500/month
    per property, accept credit card, Downtown, Near The Ocean, Resort, Town, Village, Waterfront, Communal Pool, Lawn / Garden, terrace, Balcony, Air Conditioning, Internet

Key West “SOUTHERNMOST HOSPITALITY @ UPPER DUVAL”: Superlative 5BR/5.5BA Estate + Pool..

  • 5 BR/5 BA Estate (sleeps 12)
    $1,200 - $2,100/nt
    $7,000 - $12,000/wk
    $25,500 - $41,000/month
    per property, pets considered, Downtown, Village, Private Pool, Lawn / Garden, Balcony, Air Conditioning, Internet, Satellite / Cable

Key West “GOOD DAY, SUNSHINE! @ OLD TOWN”: Sunny 2BR/2BA Cottage + Large Porch & Pool…

  • 2 BR/2 BA House (sleeps 6)
    $4,667 - $10,733/month
    per property, pets considered, Downtown, Village, Private Pool, Lawn / Garden, Air Conditioning, Internet, Satellite / Cable, Television

Key West Located in the Coveted Casa Marina Distict

  • 3 BR/1 BA House (sleeps 8)
    $5,600 - $9,800/month
    per property, pets considered, Hot Tub, Near The Ocean, Town, Private Pool, Balcony, Air Conditioning, Internet, Satellite / Cable

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 - $5,413/month
    per property, Communal Pool, Balcony, Air Conditioning, Internet, Satellite / Cable, Television, Parking

Key West EXCELLENT PRICE for an amazing townhouse with POOL and TIKI BAR!

  • 3 BR/3 BA Townhome (sleeps 8)
    $230 - $400/nt
    $1,360 - $2,500/wk
    per property, accept credit card, Near The Ocean, Communal Pool, Balcony, Fitness Room / Equipment, Air Conditioning, Internet, Satellite / Cable

Key West Amelia Home: 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 Villa Soleil: 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, DVD Player, Parking

Key West Papaya Place: 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, Communal Pool, Air Conditioning, Internet, Television, Parking

Key West Duval Street Hideaway

  • 2 BR/2 BA, 1 half bath Condo (sleeps 6)
    $240 - $478/nt
    $1,450 - $3,275/wk
    per property, Hot Tub, Communal Pool, Air Conditioning, Internet, Television, DVD Player, Parking

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

  • 3 BR House (sleeps 6)
    $27,067 - $30,933/month
    per property, accept credit card, Beach, Resort, Private Pool, Tennis Court, Air Conditioning, Internet, Satellite / Cable, Television

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 Waterfront Luxury in Old Town Key West

  • 1 BR/1 BA Condo (sleeps 5)
    $350 - $480/nt
    $2,125 - $2,900/wk
    per property, accept credit card, Hot Tub, Resort, Waterfront, Communal Pool, Sauna, Fitness Room / Equipment, Air Conditioning, Internet

Key West Brass Palm Villa, Private Luxury Home - ESCAPE TO PARADISE!!

  • 3 BR/2 BA, 1 half bath House (sleeps 6)
    $5,500 - $20,000/month
    per property, pets considered, Near The Ocean, Town, Private Pool, Lawn / Garden, Air Conditioning, Internet, Satellite / Cable, Television

Key West Margaux's Hideaway - Spacious Private Tropical Home with Pool - KEY WEST LIVING!

  • 3 BR/3 BA House (sleeps 6)
    $2,500 - $5,300/wk
    $5,500 - $8,500/month
    per property, Near The Ocean, Town, Private Pool, Lawn / Garden, Balcony, Air Conditioning, Internet, Satellite / Cable, Television

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/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 Modern home with great location - room for whole family - including pets

  • 3 BR/1 BA, 1 half bath House (sleeps 6)
    $83 - $133/nt
    per property, accept credit card, pets considered, Beach, Town, Lawn / Garden, Air Conditioning, Internet, Satellite / Cable, Television

Key West 'THE COMMANDER'S SANCTUARY @ PARADISE HARBOR': Waterfront 4BR/3.5BA Home + Dock

  • 4 BR/3 BA, 1 half bath Townhome (sleeps 12)
    $750 - $1,200/nt
    $4,400 - $6,600/wk
    $15,400 - $23,000/month
    per property, pets considered, wheelchair accessible, Downtown, Private Pool, Balcony, Air Conditioning, Internet, Satellite / Cable

Key West 'IRMA'S ESCAPE @ THE BUTTERFLY GARDEN': Tasteful 2BR/2.5BA Villa + Resort Pool

  • 2 BR/2 BA, 1 half bath Villa (sleeps 4)
    $2,800 - $5,460/month
    per property, pets considered, Village, Communal Pool, Balcony, Fitness Room / Equipment, Air Conditioning, Internet, Satellite / Cable

Key West “Waterside Retreat @ Key Haven”: Private Spacious Home on Canal + 40' Dock…

  • 4 BR/3 BA, 1 half bath House (sleeps 8)
    $5,600 - $8,867/month
    per property, pets considered, Hot Tub, Lawn / Garden, Balcony, Air Conditioning, Internet, Satellite / Cable, Television

Key West Quiet, elegant, Key West Condo close to the Ocean

  • 2 BR/2 BA Condo (sleeps 6)
    $235 - $255/nt
    $1,645 - $1,785/wk
    per property, accept credit card, pets considered, wheelchair accessible, Beach, Near The Ocean, Communal Pool, Tennis Court, Balcony, Fitness Room / Equipment

Key West Spacious Ocean Front Resort - 3 Bedroom Condo

  • 3 BR/3 BA Condo (sleeps 8)
    $350 - $500/nt
    $2,275 - $3,150/wk
    per property, accept credit card, Hot Tub, wheelchair accessible, Beach, Communal Pool, Jacuzzi, Sauna, Tennis Court

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

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

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

  • 3 BR/2 BA House Boat (sleeps 10)
    $395 - $745/nt
    $3,661 - $6,117/wk
    accept credit card, Hot Tub, Beach, Downtown, Near The Ocean, Resort, Waterfront, Communal Pool, Jacuzzi, Sauna, Balcony, Air Conditioning

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 Coral Hammock 39 - 3 Bedroom Townhouse with a Shared Pool

  • 3 BR/3 BA Townhome (sleeps 6)
    $250/nt
    $1,750 - $2,450/wk
    $7,500/month
    per property, Communal Pool, Balcony, Air Conditioning, Internet, Satellite / Cable

Key West Pelican Landing Harbor Island Retreat

  • 2 BR/2 BA Condo (sleeps 6)
    $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 Pelican Landing Bermuda 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
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