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Search over 150,000 vacation rentals properties now! Click here to see more Vacation Homes
Search for vacation rental homes in Key West
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'Hidden Treasure' @ Casa East
'HIDDEN TREASURE' @ Casa East: Luxury 3BR's, Baby Grand Piano, Huge Private Pool — Property 177317
- House
- 3 bedrooms , sleeps 6
- 3 bathrooms
- beach, near the ocean
- pool
- Rates (shown in USD)
- $1925 - $2750 per property per week
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Large Old Town 5BR home w/pool
“FALLING WATER” @ Old Town: Breathtaking 5BR Private Compound with Private Pool — Property 180171
- House
- 5 bedrooms , sleeps 12
- 4 bathrooms
- 1 half bathroom
- downtown, near the ocean
- pool
- Rates (shown in USD)
- $4250 - $8250 per property per week
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Luxury 4BR home, private pool
'COLORFUL CONCH' @ the Sanctuary: Decorator Home with 4BR/3BA & Private Pool — Property 189356
- House
- 4 bedrooms , sleeps 6
- 3 bathrooms
- beach, resort
- Rates (shown in USD)
- $1750 - $2750 per property per week
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'Southern Star' @ William
'SOUTHERN STAR' @ William Street: Luxurious 3BR/3BA Historic Old Town Home — Property 193075
- House
- 3 bedrooms , sleeps 6
- 3 bathrooms
- village, waterfront
- pool
- Rates (shown in USD)
- $1925 - $2750 per property per week
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'Southwinds' @ K.W. Beach Club
“SOUTHWINDS” @ Key West Beach Club: 2 BR Beachfront Condo, Panoramic Ocean Views — Property 204250
- Condo
- 2 bedrooms , sleeps 6
- 2 bathrooms
- beach, waterfront
- pool
- Rates (shown in USD)
- $1375 - $2475 per property per week
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Luxury home, resort style pool
'SIMPLY IRRESISTIBLE' @ The Pool: 2BR 2.5BA Luxurious Poolside Townhome — Property 206279
- Townhome
- 2 bedrooms , sleeps 6
- 2 bathrooms
- 1 half bathroom
- near the ocean, resort
- pool
- Rates (shown in USD)
- $900 - $1250 per property per week
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'Southernmost Belle'
'SOUTHERNMOST BELLE' @ The Annex: 7 Bedrooms, Huge Porches & Large Private Pool — Property 225064
- House
- 7 bedrooms , sleeps 14
- 5 bathrooms
- downtown, resort
- pool
- Rates (shown in USD)
- $6500 - $14000 per property per week
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'Georgia Peach'
'GEORGIA PEACH' in Old Town: 4BR Luxury Home @ the Meadows — Property 225229
- House
- 4 bedrooms , sleeps 10
- 4 bathrooms
- 1 half bathroom
- downtown, resort
- pool
- Rates (shown in USD)
- $1750 - $2750 per property per week
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Luxury 2BR home, private pool
'TURTLE CAY SPA' @ the Sanctuary: Walled Yard & 2 Master Suites — Property 226088
- House
- 2 bedrooms , sleeps 6
- 2 bathrooms
- near the ocean, resort
- pool
- Rates (shown in USD)
- $1250 - $1550 per property per week
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Penny's Pompei
“PENNY'S POMPEI” @ Key West Golf Club: Elegant 2BR/1.5BA Townhome — Property 229104
- House
- 2 bedrooms , sleeps 6
- 1 bathroom
- 1 half bathroom
- near the ocean, resort
- pool
- Rates (shown in USD)
- $775 - $1125 per property per week
Refine Your Search
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Bedrooms
- Studio (9)
- 1 bedroom (34)
- 2 bedrooms (151)
- 3 bedrooms (89)
- 4+ bedrooms (53)
Sleeps
- Sleeps 1-4 (112)
- Sleeps 5-8 (192)
- Sleeps 9-12 (23)
- Sleeps 13 or more (7)
Baths
- 1 bathroom (85)
- 2 bathrooms (168)
- 3 bathrooms (52)
- 4+ bathrooms (29)
Lodging Type
- apartment rentals (1)
- boat rentals (1)
- bungalow rentals (1)
- condo rentals (107)
- cottage rentals (18)
- estate rentals (1)
- house rentals (178)
- studio rentals (3)
- townhome rentals (14)
- villa rentals (4)
- yacht rentals (1)
Amenities
- air conditioning (236)
- satellite or cable tv (208)
- pool (271)
- internet access (136)
- dishwasher (231)
- washing machine (229)
Leisure Activities
- Key West rentals near fishing (292)
- Key West rentals near golf (276)
- Key West rentals near skiing (4)
Suitability
- wheelchair accessible (24)
- suitable for elderly or infirm (55)
- pet friendly (57)
- non smoking only (285)
