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Key West Rentals

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Key West 'LA DOLCE VITA' , Luxurious!, Steps To Duval! Sleeps 2-4

  • 1 BR/1 BA Condo (sleeps 4)
    $188 - $278/nt
    per property, accept credit card, Near The Ocean, Town, Balcony, Air Conditioning, Internet, Television, DVD Player

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

  • 3 BR/2 BA House Boat (sleeps 10)
    $395 - $745/nt
    $3,661 - $7,117/wk
    accept credit card, Hot Tub, Beach, Downtown, Near The Ocean, Resort, Waterfront, Communal Pool, Jacuzzi, Sauna, Balcony, Air Conditioning

Key West 'The Bungalow Too'

  • 1 BR/1 BA House (sleeps 2)
    $125 - $199/nt
    $795 - $1,295/wk
    $3,392/month
    per property, Hot Tub, Resort, Communal Pool, Lawn / Garden, Fitness Room / Equipment, Air Conditioning, Internet, Satellite / Cable

Key West Salida del Sol - Waterfront Key West Resort Style Home w/Pool & Beach

  • 2 BR/2 BA House (sleeps 6)
    $9,147/month
    per property, Beach, Near The Ocean, Town, Waterfront, Private Pool, Balcony, Air Conditioning, Internet, Satellite / Cable, Television, DVD Player

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 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 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

Key West Unique Vacation Rental on Water! Available Fantasy Fest Week Starting Oct. 27th!

  • 3 BR/2 BA Yacht (sleeps 8)
    $250 - $500/nt
    per property, accept credit card, pets considered, Communal Pool, Balcony, Fitness Room / Equipment, Air Conditioning, Satellite / Cable, Television

Key West UNBELIEVEABLE 3 Bedroom Houseboat Rental in First Class Marina w/ pool and more!

  • 4 BR/2 BA House Boat (sleeps 8)
    $350 - $500/nt
    per property, accept credit card, pets considered, Resort, Communal Pool, Sauna, Balcony, Fitness Room / Equipment, Air Conditioning

Key West Sea Breeze Cottage-Gulf View in Truman Annex

  • 3 BR/2 BA Cottage (sleeps 6)
    $2,800 - $3,500/wk
    $9,520 - $11,900/month
    per property, Beach, Downtown, Near The Ocean, Town, Waterfront, Communal Pool, Lawn / Garden, Balcony, Air Conditioning, Internet, Satellite / Cable, Television

Key West “THE IBIS & THE CRANE @ OLD TOWN”: Spacious 6BR/6+BA Compound + 2 Private Pools

  • 6 BR/6 BA, 2 half baths Townhome (sleeps 16)
    $1,400 - $2,100/nt
    $7,700 - $11,900/wk
    $26,000 - $41,000/month
    per property, pets considered, Downtown, Village, Private Pool, Lawn / Garden, Balcony, Air Conditioning, Internet, Satellite / Cable

Key West ‘THE SMILING IBIS @ OLD TOWN’: Immaculate 3BR/3.5BA Old Town Home + Private Pool

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

Key West 'THE SEAFARER'S REFUGE @ PARADISE HARBOR': Old Town Home By Water + Pool & Dock.

  • 4 BR/3 BA, 1 half bath House (sleeps 12)
    $7,000 - $13,067/month
    per property, pets considered, Downtown, Village, Private Pool, Lawn / Garden, Balcony, Air Conditioning, Internet, Satellite / Cable

Key West Island Escape Condo in Beautiful Truman Annex

  • 1 BR/1 BA Condo (sleeps 3)
    $1,200 - $1,750/wk
    $4,080 - $5,950/month
    per property, accept credit card, Beach, Downtown, Near The Ocean, Town, Waterfront, Communal Pool, Lawn / Garden, Balcony, Air Conditioning, Internet, Satellite / Cable

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 “THE MELLOW MACAW @ SOUTHERNMOST”: Cheerful 2BR/1BA + Spa Off Duval…

  • 2 BR/1 BA Condo (sleeps 6)
    $290 - $450/nt
    $1,450 - $2,350/wk
    $4,900 - $8,250/month
    per property, Hot Tub, Downtown, Village, Balcony, Air Conditioning, Internet, Satellite / Cable, Television, Parking

Key West 'AZURE MORNING @ OCEANSIDE MARINA': Lavish Oceanfront Condo + Pool....

  • 3 BR/2 BA Condo (sleeps 6)
    $2,100 - $3,200/wk
    $7,500 - $11,750/month
    per property, accept credit card, Near The Ocean, Waterfront, Communal Pool, Jacuzzi, terrace, Balcony, Fitness Room / Equipment, Air Conditioning

Key West KEY WEST LIVIN' Beautiful 50' Yacht 3 Bed, 2 Bath Sleeps 6 WIFI,Beach,Pool, Gym

  • 3 BR/2 BA Yacht (sleeps 8)
    $275 - $450/nt
    per property, pets considered, Resort, Communal Pool, Sauna, Fitness Room / Equipment, Air Conditioning, Internet, Satellite / Cable

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

  • 2 BR/1 BA, 1 half bath Townhome (sleeps 5)
    $200 - $425/nt
    $1,400 - $2,800/wk
    $4,200 - $7,800/month
    per property, Village, Communal Pool, Lawn / Garden, Balcony, Air Conditioning, Internet, Satellite / Cable, Television

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 'CONCH CASITA @ THE HISTORIC SEAPORT': Lovely 1BR/1BA Private Cottage + Spa...

  • 1 BR/1 BA Cottage (sleeps 4)
    $2,940 - $5,787/month
    per property, pets considered, Hot Tub, Downtown, Village, Lawn / Garden, Air Conditioning, Internet, Satellite / Cable, Television

Key West 'CARIBBEAN FLING @ SOUTHARD': Delightful 2BR/1.5BA Island Cottage + Private Pool

  • 2 BR/1 BA, 1 half bath House (sleeps 6)
    $3,733 - $6,813/month
    per property, pets considered, Downtown, Village, Private Pool, Air Conditioning, Internet, Satellite / Cable, Television, DVD Player

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 Adorable Cottage steps from Duval

  • 1 BR/1 BA Condo (sleeps 4)
    $2,613 - $5,133/month
    per property, Village, Communal Pool, Air Conditioning, Internet, Satellite / Cable, Television, DVD Player

Key West 'PUERTA CORALINA @ SOLARES HILL': Charming 2BR/3BA Cottage + Private Pool...

  • 2 BR/3 BA House (sleeps 6)
    $390 - $750/nt
    $2,150 - $3,950/wk
    $6,600 - $14,000/month
    per property, accept credit card, pets considered, Downtown, Town, Village, Private Pool, terrace, Balcony, Air Conditioning, Internet

Key West Truman Annex, Old Town, Key West, Private Setting with Luxury Features

  • 2 BR/2 BA, 1 half bath Townhome (sleeps 5)
    $1,750 - $3,000/wk
    $5,250 - $7,250/month
    per property, accept credit card, Beach, Downtown, Lawn / Garden, Balcony, Air Conditioning, Internet, Satellite / Cable, Television

Key West Sweet Cottage and Guest House with Large Private Pool!

  • 3 BR/2 BA, 1 half bath House (sleeps 8)
    $550 - $750/nt
    $3,550 - $4,950/wk
    per property, accept credit card, Downtown, Private Pool, Air Conditioning, Internet, Satellite / Cable, Television, DVD Player

Key West “HAVANA HOUSE @ SOLARES HILL”: Simply Elegant 3BR/2BA Cottage + Pool..

  • 3 BR/2 BA House (sleeps 8)
    $5,600 - $10,733/month
    per property, pets considered, Downtown, Village, Private Pool, Lawn / Garden, Balcony, Air Conditioning, Internet, Satellite / Cable

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

  • 3 BR/2 BA Cottage (sleeps 8)
    $425 - $825/nt
    $2,550 - $4,500/wk
    $8,000 - $16,000/month
    per property, accept credit card, pets considered, Town, Village, Private Pool, Air Conditioning, Internet, Satellite / Cable, Television

Key West “THE ADMIRAL'S COMPOUND @ PARADISE HARBOR”: 9BR/7.5BA Waterfront Estate...

  • 9 BR/7 BA, 1 half bath Estate (sleeps 24)
    $2,000 - $3,000/nt
    $11,350 - $16,600/wk
    $35,400 - $56,000/month
    per property, pets considered, Downtown, Village, Private Pool, Balcony, Air Conditioning, Internet, Satellite / Cable, Television

Key West 'THE COMMODORE'S MANOR @ PARADISE HARBOR ': Grand 5BR/4BA Waterfront Home + Dock

  • 5 BR/4 BA Townhome (sleeps 14)
    $1,250 - $1,800/nt
    $6,900 - $10,000/wk
    $20,000 - $33,000/month
    per property, accept credit card, pets considered, wheelchair accessible, Downtown, Near The Ocean, Town, Village, Waterfront, Private Pool, terrace, Balcony, Air Conditioning

Key West 'EDEN @ THE ANNEX': 2BR/1.5BA Old Town Villa near Beach & Sunset Pier...

  • 2 BR/1 BA, 1 half bath Villa (sleeps 6)
    $1,850 - $3,100/wk
    $6,000 - $10,800/month
    per property, accept credit card, Downtown, Near The Ocean, Communal Pool, Lawn / Garden, terrace, Balcony, Air Conditioning, Internet

Key West 'THE BICYCLE COTTAGE @ OLD TOWN': Iconic 2BR/2BA Lovely Island Cottage...

  • 2 BR/2 BA Cottage (sleeps 6)
    $3,733 - $7,000/month
    per property, pets considered, Downtown, Village, Lawn / Garden, Air Conditioning, Internet, Satellite / Cable, Television, DVD Player

Key West “CAYO CALYPSO @ HIGGS BEACH”: 3BR/3BA New Tropical Home + Private Pool...

  • 3 BR/3 BA House (sleeps 8)
    $5,133 - $9,287/month
    per property, Downtown, Village, Private Pool, Lawn / Garden, Balcony, Air Conditioning, Internet, Satellite / Cable, Television

Key West 'SOUTHERNMOST COMFORT @ THE ANNEX': Stunning 5BR/4BA Private Home + Pool...

  • 5 BR/4 BA House (sleeps 8)
    $7,000 - $12,000/wk
    $25,500 - $42,000/month
    per property, pets considered, Downtown, Resort, Village, Private Pool, Lawn / Garden, Balcony, Air Conditioning, Internet, Satellite / Cable

Key West Real World MTV House---Not Just a House Your Own Private Resort

  • 10 BR/5 BA, 1 half bath House (sleeps 20)
    $1,500 - $2,500/nt
    $10,000 - $12,500/wk
    $40,000 - $50,000/month
    per property, accept credit card, pets considered, Hot Tub, Resort, Waterfront, Jacuzzi, Tennis Court, Lawn / Garden, Balcony

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 “VILLA OLIVIETTA @ SOLARES HILL” - Exceptional 4BR/5BA Home + Private Pool...

  • 4 BR/4 BA, 1 half bath House (sleeps 8)
    $8,867 - $18,667/month
    per property, pets considered, Downtown, Village, Private Pool, Lawn / Garden, 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 “MURIEL'S WHIMSICAL GALLERIA @ DUVAL STREET”: Dreamy 2BR/2BA Downtown Condo...

  • 2 BR/2 BA Condo (sleeps 6)
    $2,940 - $6,300/month
    per property, accept credit card, Downtown, Resort, Balcony, Air Conditioning, Internet, Satellite / Cable, Television, DVD Player

Key West “THE CAPTAIN'S ANNEX @ PARADISE HARBOR”: Ample 4BR Home + Pool & Boat Slip...

  • 4 BR/3 BA, 1 half bath House (sleeps 12)
    $650 - $1,000/nt
    $4,000 - $6,000/wk
    $14,000 - $21,000/month
    per property, pets considered, Village, Private Pool, Balcony, Air Conditioning, Internet, Satellite / Cable, Television

Key West SWEET COTTAGE IN THE MEADOWS!

  • 3 BR/2 BA House (sleeps 6)
    $3,547 - $7,000/month
    per property, Resort, Air Conditioning, Internet, Satellite / Cable, Television

Key West 'CASA BLANCA 1888 @ WHITE': Historic 4BR/3BA Old Town Home + Very Large Pool....

  • 4 BR/3 BA House (sleeps 10)
    $7,467 - $16,333/month
    per property, accept credit card, pets considered, Downtown, Near The Ocean, Resort, Private Pool, Lawn / Garden, terrace, Balcony, Air Conditioning

Key West 'SUNSET POINT @ SUNSET MARINA': Immaculate 3BR/2BA Waterfront Condo...

  • 3 BR/2 BA Condo (sleeps 8)
    $3,920 - $7,233/month
    per property, accept credit card, pets considered, Communal Pool, Balcony, Air Conditioning, Internet, Satellite / Cable, Television

Key West 'SUNSET VISTAS @ SUNSET MARINA': Lovely 2BR/2BA Waterfront Condo + Pool...

  • 2 BR/2 BA Condo (sleeps 4)
    $2,940 - $6,160/month
    per property, pets considered, wheelchair accessible, Communal Pool, Balcony, Air Conditioning, Internet, Satellite / Cable, Television

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 '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 'NANCY'S SEASIDE RETREAT @ THE FLORIDA BAY': Waterfront 4BR/4BA Home + Pool..

  • 4 BR/4 BA House (sleeps 10)
    $5,600 - $11,667/month
    per property, pets considered, Village, Private Pool, Lawn / Garden, Balcony, Air Conditioning, Internet, Satellite / Cable
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