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