Vacation Rentals in Key West, Florida

50 Properties Available

Duval Street Stay + Free Breakfast. Private Beach Hotel
Duval Street Stay + Free Breakfast. Private Beach
$25143 / night
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Waterfront Room Retreat: Sparkling Pools | Three Spacious Rooms Private vacation home
Waterfront Room Retreat: Sparkling Pools | Three Spacious Rooms
$5912 / night
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Resort Room with Direct Access to Water Adventures | 3 Suites Ideal for Family Private vacation home
Resort Room with Direct Access to Water Adventures | 3 Suites Ideal for Family
$5583 / night
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Steps to Duval-Pool-Hot tub- Sleeps 16- BIG groups Private vacation home
Steps to Duval-Pool-Hot tub- Sleeps 16- BIG groups
$4750 / night
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1 Block to Duval St | Banana's Foster Guesthouse Apartment
1 Block to Duval St | Banana's Foster Guesthouse
$4511 / night
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WATSON HOUSE GRAND ESTATE on Simonton St Private vacation home
WATSON HOUSE GRAND ESTATE on Simonton St
$4403 / night
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Sailing Catamaran in Key West with Captain and Mate House boat
Sailing Catamaran in Key West with Captain and Mate
$3708 / night
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**A ROYAL AFFAIR @ DUVAL** Three Home Compound + LAST KEY SERVICES… Private vacation home
**A ROYAL AFFAIR @ DUVAL** Three Home Compound + LAST KEY SERVICES…
$3267 / night
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Custom House Inn | 8 BR Suite Compound on Duval! Guest house
Custom House Inn | 8 BR Suite Compound on Duval!
$3210 / night
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Real World MTV House-18 to 22 guests, Not Just a House Your Own Private Resort Private vacation home
Real World MTV House-18 to 22 guests, Not Just a House Your Own Private Resort
$3037 / night
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CLASSIC KEY WEST - Grand home in Old Town location Private vacation home
CLASSIC KEY WEST - Grand home in Old Town location
$2714 / night
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The Fairhaven House at Solaire Lunara Bay Private vacation home
The Fairhaven House at Solaire Lunara Bay
$2646 / night
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Southern snowbird-friendly house with pool, stunning backyard & great location Private vacation home
Southern snowbird-friendly house with pool, stunning backyard & great location
$2468 / night
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~ VILLA JOSINE ~ 4 B\/4.5 BA large designer home with pool in a great location Private vacation home
~ VILLA JOSINE ~ 4 B\/4.5 BA large designer home with pool in a great location
$2260 / night
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2 Sunset Harbor Resort Key West, Hot Tub, Pool! Hotel resort
2 Sunset Harbor Resort Key West, Hot Tub, Pool!
$2237 / night
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Larkshine House at Lunara Bay Private vacation home
Larkshine House at Lunara Bay
$2217 / night
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Harbor front Hideaway w\/ Pools & Seaside Dining | 1BR Spacious Suite Private vacation home
Harbor front Hideaway w\/ Pools & Seaside Dining | 1BR Spacious Suite
$2115 / night
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Key West Island Rendezvous - Private Compound Steps Off Duval w\/Pool - Sleeps 12 Private vacation home
Key West Island Rendezvous - Private Compound Steps Off Duval w\/Pool - Sleeps 12
$2069 / night
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Sunset Harbor Resort & Spa, Hot Tub, Pool Hotel resort
Sunset Harbor Resort & Spa, Hot Tub, Pool
$2053 / night
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Coastal Comfort & 3\/4 Time Compound Private vacation home
Coastal Comfort & 3\/4 Time Compound
$2049 / night
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Breathtaking Waterfront Retreat | Spacious 1BR Suite w\/ Living Area Private vacation home
Breathtaking Waterfront Retreat | Spacious 1BR Suite w\/ Living Area
$1998 / night
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Your Waterfront Hideaway in the Heart of Key West Apartment
Your Waterfront Hideaway in the Heart of Key West
$1971 / night
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2/2 Key West, Galleon Resort, Marina, In Town, Pool, Hot Tub Hotel resort
2/2 Key West, Galleon Resort, Marina, In Town, Pool, Hot Tub
$1964 / night
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Just steps to Duval- Sleeps 10- Pool House Private vacation home
Just steps to Duval- Sleeps 10- Pool House
$1882 / night
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SOUTHERNMOST BELLE~ Heated Pool, Gourmet Kitchen & Elegant Large Bedrooms! Private vacation home
SOUTHERNMOST BELLE~ Heated Pool, Gourmet Kitchen & Elegant Large Bedrooms!
$1871 / night
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Chic Waterfront Room | 1BR Suite w\/ Balcony | Outdoor Pools Apartment
Chic Waterfront Room | 1BR Suite w\/ Balcony | Outdoor Pools
$1861 / night
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Close to Nearest Beach! Four Premium Ocean View Rooms (w\/ 2 Queen Beds), Pool Hotel
Close to Nearest Beach! Four Premium Ocean View Rooms (w\/ 2 Queen Beds), Pool
$1782 / night
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Studio Galleon Resort, Hot Tub, Pool, Marina, Gym Hotel resort
Studio Galleon Resort, Hot Tub, Pool, Marina, Gym
$1764 / night
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Perfect Staycation! Four Fantastic Ocean View Rooms, Outdoor Pool Guest house
Perfect Staycation! Four Fantastic Ocean View Rooms, Outdoor Pool
$1693 / night
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Close to the Nearest Beach! Four Amazing Rooms w\/ Pool View Private vacation home
Close to the Nearest Beach! Four Amazing Rooms w\/ Pool View
$1689 / night
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4 x The Marker Classic 2 Queens at The Marker Waterfront Resort Key West Guest house
4 x The Marker Classic 2 Queens at The Marker Waterfront Resort Key West
$1665 / night
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Best Spot Near Duval Street Nightlife! Suite ScenicHarbor View and Terrace Guest house
Best Spot Near Duval Street Nightlife! Suite ScenicHarbor View and Terrace
$1635 / night
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~DREAMING ON DUVAL~ Grand 5 bedroom, 4.5 bath home with private pool\/parking Private vacation home
~DREAMING ON DUVAL~ Grand 5 bedroom, 4.5 bath home with private pool\/parking
$1632 / night
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3 Island-Chic Rooms Offering Private White Sand Beach on Duval St. in Key West Hotel
3 Island-Chic Rooms Offering Private White Sand Beach on Duval St. in Key West
$1614 / night
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Pool View 3BR Residence | Beachside Resort Condo
Pool View 3BR Residence | Beachside Resort
$1573 / night
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You Found it! Amazing Stay w\/ 4 Deluxe Pool View (w\/ Two Queen Beds Each) Hotel
You Found it! Amazing Stay w\/ 4 Deluxe Pool View (w\/ Two Queen Beds Each)
$1568 / night
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Ocean Front Presidential Suite | Beachside Resort Condo
Ocean Front Presidential Suite | Beachside Resort
$1552 / night
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Ocean Front Presidential Suite | Beachside Resort Condo
Ocean Front Presidential Suite | Beachside Resort
$1549 / night
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Ocean Front Presidential Suite | Beachside Resort Condo
Ocean Front Presidential Suite | Beachside Resort
$1549 / night
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Bright Key West House with Private Pool, Gas Grill, W/D, Central AC, & Free WiFi Private vacation home
Bright Key West House with Private Pool, Gas Grill, W/D, Central AC, & Free WiFi
$1546 / night
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Ocean Front Presidential Suite | Beachside Resort Condo
Ocean Front Presidential Suite | Beachside Resort
$1523 / night
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Ocean Front Presidential Suite | Beachside Resort Condo
Ocean Front Presidential Suite | Beachside Resort
$1523 / night
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Ocean Front Presidential Suite | Beachside Resort Condo
Ocean Front Presidential Suite | Beachside Resort
$1523 / night
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Ocean Front Presidential Suite | Beachside Resort Condo
Ocean Front Presidential Suite | Beachside Resort
$1523 / night
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Ocean Front Presidential Suite | Beachside Resort Condo
Ocean Front Presidential Suite | Beachside Resort
$1523 / night
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Ocean Front Presidential Suite | Beachside Resort Condo
Ocean Front Presidential Suite | Beachside Resort
$1523 / night
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Ocean Front Presidential Suite | Beachside Resort Condo
Ocean Front Presidential Suite | Beachside Resort
$1523 / night
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Ocean Front Presidential Suite | Beachside Resort Condo
Ocean Front Presidential Suite | Beachside Resort
$1523 / night
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MANGO MARGARITA~ 2 bedroom\/2.5 bath, heated private pool, and close to Duval! Private vacation home
MANGO MARGARITA~ 2 bedroom\/2.5 bath, heated private pool, and close to Duval!
$1506 / night
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Key West Suites Hotel - Adam Scott Rote Suite Apartment
Key West Suites Hotel - Adam Scott Rote Suite
$1500 / night
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