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Key West Vacation Rental Accommodations - Page 1 of 7

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Key West Waterfront Luxury in Old Town Key West

  • 1 BR/1 BA Condo (sleeps 5)
    $280 - $415/nt
    $1,680 - $2,750/wk
    per property, resort, waterfront, fitness room, air-conditioning, internet access, satellite or cable, TV, DVD, parking

Key West Gated Private Luxurious Getaway-Truman Annex (Private Pool)

  • 3 BR/3 BA, 1 half bath House (sleeps 7)
    $4,500 - $6,500/wk
    per property, balcony, air-conditioning, internet access, satellite or cable, TV

Key West Ocean and Sunset View in Gorgeous Truman Annex

  • 2 BR/1 BA Condo (sleeps 4)
    $1,200 - $1,800/wk
    per property, near the ocean, town, pool, balcony, air-conditioning, internet access, satellite or cable, TV, DVD

Key West Paradise manor with private pool and patio

  • 4 BR/2 BA House (sleeps 9)
    $100/nt
    per property, near the ocean, garden, air-conditioning, internet access, satellite or cable, TV, DVD, barbecue

Key West Beautiful Duval St. Condo, Location, Location!!!!

  • 2 BR/1 BA Condo (sleeps 4)
    $200 - $250/nt
    $1,000 - $1,400/wk
    $4,000 - $5,000/month
    per property, downtown, near the ocean, balcony, pets considered, air-conditioning, internet access, satellite or cable, TV, DVD

Key West (Quiet) House with Guest Cottage

  • 3 BR/3 BA, 1 half bath House (sleeps 8)
    $6,500 - $9,900/month
    per property, beach, near the ocean, pool, pets considered, air-conditioning, internet access, satellite or cable, TV, DVD

Key West 'NATALIE'S BAHAMA CONCH': Lavish 3BR/2.5BA Home w/ Private Pool @ the Sanctuary

  • 3 BR/2 BA, 1 half bath House (sleeps 7)
    $7,000 - $9,900/month
    per property, near the ocean, resort, pool, pool, terrace, balcony, pets considered, fitness room, air-conditioning

Key West “NOONA'S MANSION-by-the-SEA”: Oceanfront 6BR/5.5BA @ Truman Annex, Private Pool

  • 6 BR/5 BA, 1 half bath House (sleeps 14)
    $7,700 - $16,000/wk
    $21,000 - $37,500/month
    per property, pool, garden, balcony, pets considered, air-conditioning, internet access, satellite or cable, TV

Key West “NINA'S PENTHOUSE on the BEACH” 3BR/3BA 2-Story Condo @ The Key West Beach Club

  • 3 BR/3 BA Condo (sleeps 8)
    $7,700 - $10,500/month
    per property, beach, resort, pool, jacuzzi, tennis court, terrace, balcony, fitness room, air-conditioning

Key West “CASA BLANCA 1888' @ White Street: Private Home in Old Town, 4BR & Large Pool

  • 4 BR/3 BA House (sleeps 10)
    $7,000 - $12,000/month
    per property, downtown, resort, pool, garden, terrace, balcony, pets considered, air-conditioning, internet access
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Key West “SOUTHERNMOST ARTS & CRAFTS”, 2BR/2BA Private Home @ South Street

  • 2 BR/2 BA House (sleeps 6)
    $7,900 - $8,800/month
    per property, downtown, near the ocean, pool, garden, air-conditioning, internet access, satellite or cable, TV, DVD

Key West “ANGEL CONCH” @ Angela Street: Heavenly 3BR Home in Old Town

  • 3 BR/3 BA House (sleeps 6)
    $5,500 - $10,000/month
    per property, downtown, resort, jacuzzi, garden, terrace, balcony, air-conditioning, internet access, satellite or cable

Key West “CONCH-by-the-POOL' 2BR 2.5BA Luxury Townhome @ Key West Golf Club

  • 2 BR/2 BA, 1 half bath Townhome (sleeps 6)
    $2,950 - $4,200/month
    per property, near the ocean, resort, pool, balcony, air-conditioning, internet access, satellite or cable, TV, DVD

Key West 'WATER'S EDGE' @ Gulfview Pointe: Luxurious 4BR Home on Florida Bay

  • 4 BR/2 BA, 1 half bath House (sleeps 10)
    $6,600 - $11,000/month
    per property, near the ocean, waterfront, pool, balcony, pets considered, air-conditioning, internet access, TV, DVD

Key West 'TOP 'O THE COPA' @ Duval: Gorgeous Old Town Penthouse, Available Nightly

  • 1 BR/1 BA, 1 half bath Condo (sleeps 4)
    $375 - $400/nt
    $1,675 - $2,400/wk
    $5,500 - $6,600/month
    per property, downtown, village, terrace, balcony, pets considered, air-conditioning, internet access, satellite or cable, TV

Key West “PENNY'S POMPEI” @ Key West Golf Club: Elegant 2BR/1.5BA Townhome

  • 2 BR/1 BA, 1 half bath House (sleeps 6)
    $3,100 - $4,500/month
    per property, near the ocean, resort, pool, pool, terrace, balcony, pets considered, air-conditioning, internet access

Key West 'TURTLE CAY SPA' @ the Sanctuary: Walled Yard & 2 Master Suites

  • 2 BR/2 BA House (sleeps 6)
    $5,000 - $6,200/month
    per property, near the ocean, resort, pool, pool, jacuzzi, garden, balcony, pets considered, fitness room

Key West 'GEORGIA PEACH' in Old Town: 4BR Luxury Home @ the Meadows

  • 4 BR/4 BA, 1 half bath House (sleeps 10)
    $7,000 - $11,000/month
    per property, downtown, resort, pool, terrace, pets considered, air-conditioning, internet access, satellite or cable, TV

Key West 'SOUTHERNMOST BELLE' @ The Annex: 7 Bedrooms, Huge Porches & Large Private Pool

  • 7 BR/5 BA House (sleeps 14)
    $7,700 - $14,000/wk
    $20,000 - $33,000/month
    per property, downtown, resort, pool, jacuzzi, garden, balcony, pets considered, air-conditioning, internet access

Key West 'SIMPLY IRRESISTIBLE' @ The Pool: 2BR 2.5BA Luxurious Poolside Townhome

  • 2 BR/2 BA, 1 half bath Townhome (sleeps 6)
    $3,600 - $5,000/month
    per property, near the ocean, resort, pool, balcony, pets considered, air-conditioning, internet access, satellite or cable, TV
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Key West “SOUTHWINDS” @ Key West Beach Club: 2 BR Beachfront Condo, Panoramic Ocean Views

  • 2 BR/2 BA Condo (sleeps 6)
    $5,500 - $9,900/month
    per property, beach, waterfront, pool, tennis court, balcony, pets considered, fitness room, air-conditioning, internet access

Key West 'AZURE MORNING' @ Kings Pointe: Luxurious 3 Bedroom Condo on the Atlantic

  • 3 BR Condo (sleeps 8)
    $1,600 - $3,300/wk
    $4,800 - $7,700/month
    per property, near the ocean, waterfront, pool, terrace, balcony, pets considered, air-conditioning, internet access, satellite or cable

Key West “MANATEE MANOR” @ Geiger Key: 3BR 2BA Luxurious Canalside Private Home, 60’ Dock

  • 3 BR/2 BA House (sleeps 8)
    $4,950 - $5,500/month
    per property, near the ocean, waterfront, jacuzzi, balcony, pets considered, air-conditioning, internet access, satellite or cable, TV

Key West 'SOUTHERN STAR' @ William Street: Luxurious 3BR/3BA Historic Old Town Home

  • 3 BR/3 BA House (sleeps 6)
    $7,700 - $11,000/month
    per property, village, waterfront, pool, jacuzzi, balcony, pets considered, air-conditioning, internet access, satellite or cable

Key West 'COLORFUL CONCH' @ the Sanctuary: Decorator Home with 4BR/3BA & Private Pool

  • 4 BR/3 BA House (sleeps 6)
    $8,000 - $11,000/month
    per property, beach, resort

Key West 'OLD TOWN OASIS' @ Truman Annex: Spacious 2 BR Oceanfront Condo

  • 2 BR/2 BA Condo (sleeps 6)
    $2,400 - $3,950/wk
    $8,000 - $9,900/month
    per property, downtown, waterfront, balcony, air-conditioning, internet access, satellite or cable, TV, DVD, barbecue

Key West “FALLING WATER” @ Old Town: Breathtaking 5BR Private Compound with Private Pool

  • 5 BR/4 BA, 1 half bath House (sleeps 12)
    $17,000 - $33,000/month
    per property, downtown, near the ocean, pool, jacuzzi, garden, air-conditioning, internet access, satellite or cable, TV

Key West 'HIDDEN TREASURE' @ Casa East: Luxury 3BR's, Baby Grand Piano, Huge Private Pool

  • 3 BR/3 BA House (sleeps 6)
    $8,900 - $11,000/month
    per property, beach, near the ocean, pool, garden, terrace, balcony, pets considered, air-conditioning, internet access

Key West 'CONCH CASA GRANDE' @ Truman Annex: 11' Ceilings, Private Pool & 6 Master Suites

  • 7 BR/7 BA House (sleeps 12)
    $7,000 - $14,000/wk
    $21,000 - $33,000/month
    per property, downtown, near the ocean, balcony, pets considered, air-conditioning, internet access, satellite or cable, TV, DVD

Key West Luxurious Ocean Front Oasis in Key West

  • 3 BR/2 BA Condo (sleeps 6)
    $550/nt
    $2,500 - $3,500/wk
    per property, beach, waterfront, tennis court, garden, balcony, internet access, TV, DVD, parking
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Key West The Perfect Get-away in Paradise

  • Studio/1 BA Condo (sleeps 4)
    $99 - $115/nt
    per property, near the ocean, town, balcony, air-conditioning, internet access, satellite or cable, TV

Key West Villa Soleil-Enjoy America's Caribbean with Style and Comfort

  • 2 BR/2 BA, 1 half bath Townhome (sleeps 6)
    $2,000 - $2,500/wk
    per property, near the ocean, town, garden, terrace, balcony, pets considered, air-conditioning, internet access, satellite or cable

Key West Key West By Beach & Duval Street Old Town

  • 5 BR/4 BA House (sleeps 12)
    $750 - $1,000/nt
    $5,700 - $6,700/wk
    per property, downtown, near the ocean, pool, garden, terrace, balcony, air-conditioning, internet access, satellite or cable

Key West Spacious Ocean Front Resort - 3 Bedroom Condo

  • 3 BR/3 BA Condo (sleeps 8)
    $400 - $500/nt
    $2,500 - $3,150/wk
    per property, beach, sauna, tennis court, garden, terrace, balcony, air-conditioning, internet access

Key West Tropical Retreat.

  • 4 BR/3 BA House (sleeps 7)
    $4,700 - $7,500/month
    per property, downtown, pool, daily maid service, jacuzzi, pets considered, air-conditioning, satellite or cable, TV

Key West Island Spice

  • 2 BR/2 BA, 1 half bath House (sleeps 6)
    $600 - $3,190/wk
    per house, beach, clothes dryer, DVD, family, fishing, refrigerator, golf, non smoking only

Key West The Victoria House

  • 5 BR/5 BA, 1 half bath House (sleeps 12)
    $100 - $1,305/nt
    $500 - $8,200/wk
    per house, adventure, air-conditioning, balcony, beach, blender, clothes dryer, cycling, deck wood

Key West Casa de Cuba

  • 3 BR/2 BA House (sleeps 6)
    $450 - $790/nt
    $3,010 - $5,530/wk
    per house, beach, deck wood, family, non smoking only, outlet shopping, parking off street, sight seeing, unscreened porch/lanai

Key West La Brisa #405E

  • 2 BR/2 BA Condo (sleeps 4)
    $200 - $370/nt
    $1,330 - $2,590/wk
    per condo, balcony, beach, beach towels, clothes dryer, family, satellite or cable, sight seeing, telephone

Key West DIRECT OCEANFRONT FREE WIFI & HBO

  • 3 BR/2 BA, 1 half bath Condo (sleeps 6)
    $400 - $550/nt
    $2,600 - $3,350/wk
    $7,800 - $10,050/month
    per property, beach, pool, tennis court, balcony, air-conditioning, internet access, satellite or cable, TV
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Key West Ocean Retreat - 1 Week Minimum

  • 3 BR/2 BA, 1 half bath Villa (sleeps 6)
    $2,400 - $4,400/wk
    per villa, coffee maker, toaster, children welcome, pets considered, broadband access, communal pool, wireless broadband, heated pool

Key West “HEAVENLY ZEN @ GRINNELL”: 4BR Private Home @ The Historic Seaport

  • 4 BR/3 BA House (sleeps 8)
    $7,700 - $11,000/month
    per property, downtown, resort, pool, jacuzzi, garden, terrace, balcony, pets considered, air-conditioning

Key West Ocean Front Condo at 1800 Atlantic - Next to Smathers Beach

  • 2 BR/2 BA Condo (sleeps 6)
    $2,450/wk
    $5,950/month
    beach, resort, tennis court, garden, balcony, air-conditioning, internet access, satellite or cable, TV

Key West Key West - Poolside Conch Paradise at Key West Golf Club

  • 2 BR/1 BA, 1 half bath Townhome (sleeps 4)
    $1,950/wk
    $4,000/month
    per property, beach, near the ocean, pool, garden, balcony, fitness room, air-conditioning, satellite or cable, TV

Key West Duval Sea Turtle

  • 2 BR/2 BA, 1 half bath House (sleeps 6)
    $75 - $435/nt
    $500 - $2,610/wk
    per house, adventure, air-conditioning, balcony, beach, blender, DVD, family, fishing

Key West Havana Lane

  • 2 BR/2 BA House (sleeps 4)
    $310 - $530/nt
    $2,100 - $3,710/wk
    per house, clothes dryer, deck wood, grill, indoor hot tub, non smoking only, outlet shopping, satellite or cable, sight seeing

Key West The Mermaids House - Old Town, Historic Bahama Conch House

  • 2 BR/1 BA House (sleeps 6)
    $2,000/wk
    $6,000/month
    per property, near the ocean, garden, air-conditioning, internet access, satellite or cable, TV, DVD, parking

Key West 'Old Town' Key West Charmer

  • 3 BR/3 BA House (sleeps 14)
    $159 - $259/nt
    per property, near the ocean, town, balcony, air-conditioning, satellite or cable, TV, parking

Key West Wow*Key West's Best Luxury 'Oceanfront' Marina/Condo/Pool

  • 3 BR/2 BA Condo (sleeps 8)
    $8,000/month
    per property, near the ocean, pool, balcony, pets considered, air-conditioning, internet access, satellite or cable, TV

Key West Top-floor Smathers Beach condo with gorgeous pool, tennis and steps from beach.

  • 2 BR/2 BA Condo (sleeps 4)
    $1,325 - $2,450/wk
    $4,800 - $5,850/month
    per property, beach, pool, sauna, tennis court, balcony, air-conditioning, satellite or cable, TV
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