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Smathers Beach Vacation Rentals With Beach
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Current Item
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· near Smathers Beach
Beach Paradise in the Keys! Location! Location! 2 Blocks to Duval St
2 Beds · 3 baths
· Sleeps 8
·
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High Ceilings · Hardwood Floor · Dishwasher ·
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From
$718
/night
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High Ceilings
Hardwood Floor
Dishwasher
Oven
Wifi
Pool
Air Conditioning
Beach
Other spaces
Kitchen, Balcony
Current Item
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· near Smathers Beach
Henry's Penthouse on the Ocean in Key West (weekly / nightly rentals)
2 Beds · 2 baths
· Sleeps 5
·
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Ocean · Hot Tub · Dishwasher ·
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From
$515
/night
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Amenities
Ocean
Hot Tub
Dishwasher
Waterfront
Oven
Wifi
Pool
Air Conditioning
Other spaces
Kitchen, Balcony
Current Item
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· near Smathers Beach
Key West Treehouse in Old Town
1 Bed · 2 baths
· Sleeps 4
·
More
Dishwasher · Oven · Wifi ·
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From
$239
/night
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Amenities
Dishwasher
Oven
Wifi
Air Conditioning
Beach
Furnished
In Unit Laundry
Other spaces
Kitchen, Balcony, Workspace
Current Item
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· near Smathers Beach
Peaceful Setting Amongst The Active Island Life Style
2 Beds · 2 baths
· Sleeps 4
·
More
Walk In Closets · Outdoor Space · Ocean ·
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From
$585
/night
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Walk In Closets
Ocean
Dishwasher
Waterfront
Fitness Center
Oven
Wifi
Assigned Parking
Other spaces
Kitchen, Balcony
Current Item
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· near Smathers Beach
BOTTOMS UP BUNGALOW - 2 Bedroom / 2 Bathroom With PRIVATE POOL
2 Beds · 2 baths
· Sleeps 6
·
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Fireplace · Private Pool · Hardwood Floor ·
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From
$650
/night
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Fireplace
Private Pool
Hardwood Floor
Hot Tub
Dishwasher
Oven
Wifi
Assigned Parking
Other spaces
Kitchen, Balcony
Current Item
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· near Smathers Beach
Panoramic 3BR/3BA Condo - Direct Beach Ocean Front
3 Beds · 3 baths
· Sleeps 8
·
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Outdoor Space · Ocean · Hot Tub ·
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From
$800
/night
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Amenities
Ocean
Hot Tub
Dishwasher
Waterfront
Fitness Center
Oven
Wifi
Pool
Other spaces
Kitchen, Balcony, Workspace
Current Item
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· near Smathers Beach
The Galleon Resort in Beautiful Key West. Amazing Views! Over 500 Reviews!
2 Beds · 2 baths
· Sleeps 6
·
More
Hot Tub · Dishwasher · Oven ·
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From
$670
/night
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Amenities
Hot Tub
Dishwasher
Oven
Wifi
Pool
Air Conditioning
Beach
Furnished
Other spaces
Kitchen, Balcony
Current Item
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· near Smathers Beach
BEACH HOUSE~ Stunning 4B/4Ba Home with Private Pool in Truman Annex!
4 Beds · 4 baths
· Sleeps 8
·
More
Ceiling Fan · Private Pool · High Ceilings ·
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From
$1,519
/night
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Amenities
Ceiling Fan
Private Pool
High Ceilings
Hardwood Floor
Dishwasher
Fitness Center
Oven
Wifi
Other spaces
Kitchen, Balcony
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Current Item
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· near Smathers Beach
Quiet, Quaint, and Conveniently Located! New POOL!
Studio · 1 bath
· Sleeps 2
·
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Ski In Ski Out · Outdoor Space · Fitness Center ·
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From
$209
/night
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Ski In Ski Out
Fitness Center
Wifi
Pool
Air Conditioning
Beach
Furnished
In Unit Laundry
Other spaces
Kitchen
Current Item
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· near Smathers Beach
Colorful beachfront condo w/ ocean view balcony & shared hot tub/pool/tennis!
2 Beds · 2 baths
· Sleeps 6
·
More
Ocean · Hot Tub · Dishwasher ·
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From
$240
/night
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Ocean
Hot Tub
Dishwasher
Waterfront
Fitness Center
Oven
Wifi
Assigned Parking
Other spaces
Kitchen, Balcony
Current Item
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· near Smathers Beach
Location, location, location - Walk to the Beach!
1 Bed · 1 bath
· Sleeps 2
·
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Fitness Center · Oven · Wifi ·
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From
$400
/night
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Amenities
Fitness Center
Oven
Wifi
Air Conditioning
Beach
Furnished
In Unit Laundry
Residents Lounge
Other spaces
Kitchen, Workspace
Current Item
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· near Smathers Beach
Sunny Condo w/ Entertainment, Balcony, & Great Location Near Beach - Dogs OK
1 Bed · 1 bath
· Sleeps 4
·
More
On Site Laundry · Waterfront · Oven ·
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From
$103
/night
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Amenities
On Site Laundry
Waterfront
Oven
Wifi
Air Conditioning
Beach
Furnished
In Unit Laundry
Other spaces
Kitchen, Balcony
Current Item
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· near Smathers Beach
Comfy Dog-Friendly Retreat with Shared Hot Tubs, Patio - Great Old Town Location
Studio · 1 bath
· Sleeps 4
·
More
Hot Tub · Wifi · Kitchen ·
More
From
$121
/night
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Hot Tub
Wifi
Air Conditioning
Beach
Furnished
In Unit Laundry
Other spaces
Kitchen
Current Item
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· near Smathers Beach
OCEAN FRONT PENTHOUSE GALLEON.12/17/22-12/24/22.THREE BEDROOM-C BLDG
3 Beds · 3 baths
· Sleeps 9
·
More
On Site Laundry · High Ceilings · Ocean ·
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From
$714
/night
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Amenities
On Site Laundry
High Ceilings
Ocean
Hot Tub
Dishwasher
Waterfront
Fitness Center
Oven
Other spaces
Kitchen, Balcony
Current Item
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· near Smathers Beach
Superb Location! Pet-friendly, 3 Pools, Near Duval Street!
1 Bed · 1 bath
· Sleeps 4
·
More
Waterfront · Fitness Center · Balcony ·
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From
$843
/night
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Amenities
Waterfront
Fitness Center
Pool
Air Conditioning
Beach
Furnished
In Unit Laundry
Concierge Service
Other spaces
Balcony, Workspace
Current Item
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· near Smathers Beach
Perfect Location! Harbor View, Pet-friendly, Bicycle Rentals
1 Bed · 1 bath
· Sleeps 2
·
More
Waterfront · Fitness Center · Balcony ·
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From
$827
/night
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Amenities
Waterfront
Fitness Center
Pool
Air Conditioning
Beach
Furnished
In Unit Laundry
Concierge Service
Other spaces
Balcony, Workspace
Current Item
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· near Smathers Beach
Dream Vacation! Near Famous Duval Street!
1 Bed · 1 bath
· Sleeps 2
·
More
Waterfront · Fitness Center · Balcony ·
More
From
$669
/night
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Amenities
Waterfront
Fitness Center
Pool
Air Conditioning
Beach
Furnished
In Unit Laundry
Concierge Service
Other spaces
Balcony, Workspace
Current Item
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· near Smathers Beach
Great Location & Amenities! Pool & Garden View, Pets Allowed, Onsite Dining!
1 Bed · 1 bath
· Sleeps 2
·
More
Waterfront · Fitness Center · Balcony ·
More
From
$624
/night
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Amenities
Waterfront
Fitness Center
Pool
Air Conditioning
Beach
Furnished
In Unit Laundry
Concierge Service
Other spaces
Balcony, Workspace
Current Item
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· near Smathers Beach
Ultimate Vacation! Harbor View, 3 Pools, Pets Allowed!
1 Bed · 1 bath
· Sleeps 2
·
More
Waterfront · Fitness Center · Balcony ·
More
From
$1,321
/night
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Amenities
Waterfront
Fitness Center
Pool
Air Conditioning
Beach
Furnished
In Unit Laundry
Concierge Service
Other spaces
Balcony, Workspace
Current Item
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· near Smathers Beach
Look No More! Onsite Dining, Bicycle Rental, Pets Allowed, 3 Swimming Pools!
1 Bed · 1 bath
· Sleeps 4
·
More
Waterfront · Fitness Center · Balcony ·
More
From
$1,575
/night
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Amenities
Waterfront
Fitness Center
Pool
Air Conditioning
Beach
Furnished
In Unit Laundry
Concierge Service
Other spaces
Balcony, Workspace
Current Item
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· near Smathers Beach
Adventure Awaits! Partial Harbor View, Onsite Dining, 2 Blocks Away From Duval!
1 Bed · 1 bath
· Sleeps 2
·
More
Waterfront · Fitness Center · Balcony ·
More
From
$902
/night
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Amenities
Waterfront
Fitness Center
Pool
Air Conditioning
Beach
Furnished
In Unit Laundry
Concierge Service
Other spaces
Balcony, Workspace
Current Item
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· near Smathers Beach
Newly Renovated Luxury Coastal Home in the Heart of Old Town Key West
4 Beds · 4 baths
· Sleeps 12
·
More
Ceiling Fan · Outdoor Space · Hot Tub ·
More
From
$675
/night
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Amenities
Ceiling Fan
Hot Tub
Dishwasher
Fitness Center
Oven
Wifi
Air Conditioning
Beach
Other spaces
Kitchen, Workspace
Current Item
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· near Smathers Beach
Elegant Key West Tree House
2 Beds · 1 bath
· Sleeps 4
·
More
On Site Laundry · High Ceilings · Hardwood Floor ·
More
From
$159
/night
Check availability
Amenities
On Site Laundry
High Ceilings
Hardwood Floor
Dishwasher
Oven
Wifi
Air Conditioning
Beach
Other spaces
Kitchen, Balcony, Workspace
Current Item
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· near Smathers Beach
Sailing Catamaran in Key West with Captain and Chef/Hostess
3 Beds · 3 baths
· Sleeps 6
·
More
Ocean · Waterfront · Fitness Center ·
More
From
$2,385
/night
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Amenities
Ocean
Waterfront
Fitness Center
Oven
Pool
Air Conditioning
Beach
Furnished
Other spaces
Kitchen, Workspace
Current Item
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· near Smathers Beach
Nansea's Flat
2 Beds · 2 baths
·
More
Walk In Closets · Dishwasher · Oven ·
More
From
$129
/night
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Amenities
Walk In Closets
Dishwasher
Oven
Wifi
Assigned Parking
Pool
Air Conditioning
Beach
Other spaces
Kitchen
Current Item
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· near Smathers Beach
Island Time - Modern Condo, Steps To The Beach!
2 Beds · 2 baths
· Sleeps 8
·
More
On Site Laundry · Walk In Closets · Hot Tub ·
More
From
$600
/night
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Amenities
On Site Laundry
Walk In Closets
Hot Tub
Dishwasher
Oven
Wifi
Pool
Air Conditioning
Other spaces
Kitchen, Balcony
Current Item
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· near Smathers Beach
*****$$$ HUGE DISCOUNT FOR SEPT 22 $$$ OCEAN FRONT- 90 FT BALCONY****
3 Beds · 2 baths
· Sleeps 6
·
More
Walk In Closets · Outdoor Space · Ocean ·
More
From
$524
/night
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Amenities
Walk In Closets
Ocean
Hot Tub
Dishwasher
Waterfront
Fitness Center
Oven
Wifi
Other spaces
Kitchen, Balcony, Workspace
Current Item
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· near Smathers Beach
2 x Avalon Two Queen - Adults Only at The Guesthouses at Southernmost Beach
2 Beds · 2 baths
· Sleeps 8
·
More
Assigned Parking · Workspace · Pool ·
More
From
$982
/night
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Amenities
Assigned Parking
Pool
Air Conditioning
Beach
Furnished
In Unit Laundry
Swimming Pool
Concierge Service
Other spaces
Workspace
Current Item
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· near Smathers Beach
4 x Duval Gardens Two Queen - Adults Only at The Guesthouses at Southernmost
4 Beds · 4 baths
· Sleeps 16
·
More
Assigned Parking · Workspace · Pool ·
More
From
$2,950
/night
Check availability
Amenities
Assigned Parking
Pool
Air Conditioning
Beach
Furnished
In Unit Laundry
Swimming Pool
Concierge Service
Other spaces
Workspace
Current Item
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· near Smathers Beach
Experience All Of What Key West Has To Offer! Beach Access, 3 Pools, Bar!
1 Bed · 1 bath
· Sleeps 2
·
More
Assigned Parking · Workspace · Pool ·
More
From
$491
/night
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Amenities
Assigned Parking
Pool
Air Conditioning
Beach
Furnished
In Unit Laundry
Swimming Pool
Concierge Service
Other spaces
Workspace
Current Item
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· near Smathers Beach
Laidback Oceanfront Bar and Recreation Area! 3 Great Units By The Beach
3 Beds · 3 baths
· Sleeps 12
·
More
Assigned Parking · Workspace · Pool ·
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From
$1,352
/night
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Amenities
Assigned Parking
Pool
Air Conditioning
Beach
Furnished
In Unit Laundry
Swimming Pool
Concierge Service
Other spaces
Workspace
Current Item
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· near Smathers Beach
Delight In Historic Old Town Key West! Beautiful Stay Minutes From Duval Street!
1 Bed · 1 bath
· Sleeps 2
·
More
Assigned Parking · Workspace · Pool ·
More
From
$566
/night
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Amenities
Assigned Parking
Pool
Air Conditioning
Beach
Furnished
In Unit Laundry
Swimming Pool
Concierge Service
Other spaces
Workspace
Current Item
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· near Smathers Beach
Experience All Of What Key West Has To Offer! 2 Great Units, Pools, Beach Access
2 Beds · 2 baths
· Sleeps 8
·
More
Assigned Parking · Workspace · Pool ·
More
From
$1,167
/night
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Amenities
Assigned Parking
Pool
Air Conditioning
Beach
Furnished
In Unit Laundry
Swimming Pool
Concierge Service
Other spaces
Workspace
Current Item
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· near Smathers Beach
Duval Gardens King Adults Only at The Guesthouses at Southernmost Beach Resort
1 Bed · 1 bath
· Sleeps 2
·
More
Assigned Parking · Workspace · Pool ·
More
From
$522
/night
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Amenities
Assigned Parking
Pool
Air Conditioning
Beach
Furnished
In Unit Laundry
Swimming Pool
Concierge Service
Other spaces
Workspace
Current Item
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· near Smathers Beach
Wonderful Stay, Amazing Location! 4 Relaxing Units, 3 Pools!
4 Beds · 4 baths
· Sleeps 16
·
More
Assigned Parking · Workspace · Pool ·
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From
$2,940
/night
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Amenities
Assigned Parking
Pool
Air Conditioning
Beach
Furnished
In Unit Laundry
Swimming Pool
Concierge Service
Other spaces
Workspace
Current Item
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· near Smathers Beach
Duval Street where Old Town meets the Atlantic! 4 Classy Units, Near Beach
4 Beds · 4 baths
· Sleeps 16
·
More
Assigned Parking · Workspace · Pool ·
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From
$2,950
/night
Check availability
Amenities
Assigned Parking
Pool
Air Conditioning
Beach
Furnished
In Unit Laundry
Swimming Pool
Concierge Service
Other spaces
Workspace
Current Item
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· near Smathers Beach
Great for Family Trips! 2 Classy Units, Pool, Near Key West Aquarium
2 Beds · 2 baths
· Sleeps 8
·
More
Assigned Parking · Workspace · Pool ·
More
From
$1,424
/night
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Amenities
Assigned Parking
Pool
Air Conditioning
Beach
Furnished
In Unit Laundry
Swimming Pool
Concierge Service
Other spaces
Workspace
Current Item
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· near Smathers Beach
Duval Gardens Queen Adults Only at The Guesthouses at Southernmost Beach Resort
1 Bed · 1 bath
· Sleeps 2
·
More
Assigned Parking · Workspace · Pool ·
More
From
$418
/night
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Amenities
Assigned Parking
Pool
Air Conditioning
Beach
Furnished
In Unit Laundry
Swimming Pool
Concierge Service
Other spaces
Workspace
Current Item
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· near Smathers Beach
Step Out onto Legendary Duval Street! 2 Classy Units, Beach Access!
2 Beds · 2 baths
· Sleeps 8
·
More
Assigned Parking · Workspace · Pool ·
More
From
$982
/night
Check availability
Amenities
Assigned Parking
Pool
Air Conditioning
Beach
Furnished
In Unit Laundry
Swimming Pool
Concierge Service
Other spaces
Workspace
Current Item
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Details
· near Smathers Beach
3 x Duval Gardens Two Queen - Adults Only at The Guesthouses at Southernmost
3 Beds · 3 baths
· Sleeps 12
·
More
Assigned Parking · Workspace · Pool ·
More
From
$2,136
/night
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Amenities
Assigned Parking
Pool
Air Conditioning
Beach
Furnished
In Unit Laundry
Swimming Pool
Concierge Service
Other spaces
Workspace
Current Item
1
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Details
· near Smathers Beach
Avalon King - Adults Only at The Guesthouses at Southernmost Beach Resort
1 Bed · 1 bath
· Sleeps 2
·
More
Assigned Parking · Workspace · Pool ·
More
From
$542
/night
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Amenities
Assigned Parking
Pool
Air Conditioning
Beach
Furnished
In Unit Laundry
Swimming Pool
Concierge Service
Other spaces
Workspace
Current Item
1
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Details
· near Smathers Beach
Avalon Cozy Queen - Adults Only at The Guesthouses at Southernmost Beach Resort
1 Bed · 1 bath
· Sleeps 2
·
More
Assigned Parking · Workspace · Pool ·
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From
$316
/night
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Amenities
Assigned Parking
Pool
Air Conditioning
Beach
Furnished
In Unit Laundry
Swimming Pool
Concierge Service
Other spaces
Workspace
Current Item
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· near Smathers Beach
Your Relaxing Getaway Awaits! Onsite Bar, Access to 2 Beaches, 3 Pools!
1 Bed · 1 bath
· Sleeps 2
·
More
Assigned Parking · Workspace · Pool ·
More
From
$476
/night
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Amenities
Assigned Parking
Pool
Air Conditioning
Beach
Furnished
In Unit Laundry
Swimming Pool
Concierge Service
Other spaces
Workspace
Current Item
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Details
· near Smathers Beach
Wonderful Place To Stay! 3 Pools, Bar, Near Southernmost Point
1 Bed · 1 bath
· Sleeps 2
·
More
Assigned Parking · Workspace · Pool ·
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From
$455
/night
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Amenities
Assigned Parking
Pool
Air Conditioning
Beach
Furnished
In Unit Laundry
Swimming Pool
Concierge Service
Other spaces
Workspace
Current Item
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· near Smathers Beach
Key West Experience like No Other! Epicenter of Dining and Nightlife! 3 Pools
1 Bed · 1 bath
· Sleeps 2
·
More
Assigned Parking · Workspace · Pool ·
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From
$401
/night
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Amenities
Assigned Parking
Pool
Air Conditioning
Beach
Furnished
In Unit Laundry
Swimming Pool
Concierge Service
Other spaces
Workspace
Current Item
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Details
· near Smathers Beach
Welcome to Paradise! 3 pools, Beach Access, Near Duval Street!
1 Bed · 1 bath
· Sleeps 2
·
More
Assigned Parking · Workspace · Pool ·
More
From
$551
/night
Check availability
Amenities
Assigned Parking
Pool
Air Conditioning
Beach
Furnished
In Unit Laundry
Swimming Pool
Concierge Service
Other spaces
Workspace
Current Item
1
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Details
· near Smathers Beach
Duval Gardens Queen + Twin - Adults Only at The Guesthouses at Southernmost
1 Bed · 1 bath
· Sleeps 2
·
More
Assigned Parking · Workspace · Pool ·
More
From
$551
/night
Check availability
Amenities
Assigned Parking
Pool
Air Conditioning
Beach
Furnished
In Unit Laundry
Swimming Pool
Concierge Service
Other spaces
Workspace
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· near Smathers Beach
3 x Avalon Two Queens - Adults Only at The Guesthouses at Southernmost Beach
3 Beds · 3 baths
· Sleeps 12
·
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Assigned Parking · Workspace · Pool ·
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From
$1,115
/night
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Amenities
Assigned Parking
Pool
Air Conditioning
Beach
Furnished
In Unit Laundry
Swimming Pool
Concierge Service
Other spaces
Workspace
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· near Smathers Beach
Your Beach Adventure Awaits! Pool View, 3 Pools, Short Drive to Jackson Square!
1 Bed · 1 bath
· Sleeps 2
·
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Assigned Parking · Workspace · Pool ·
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From
$525
/night
Check availability
Amenities
Assigned Parking
Pool
Air Conditioning
Beach
Furnished
In Unit Laundry
Swimming Pool
Concierge Service
Other spaces
Workspace
Current Item
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· near Smathers Beach
Welcome to Paradise! Lavish and Relaxing 3 Classy Units, Enjoy the On-site Pool!
3 Beds · 3 baths
· Sleeps 12
·
More
Assigned Parking · Workspace · Pool ·
More
From
$2,212
/night
Check availability
Amenities
Assigned Parking
Pool
Air Conditioning
Beach
Furnished
In Unit Laundry
Swimming Pool
Concierge Service
Other spaces
Workspace
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Updated: March 9, 2023
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