Smathers Beach Key West Vacation Rentals
PRICE PER NIGHT
ACCOMMODATION TYPES
True Paradise: Luxury Marina Resort *3 Month Minumum Rental*
10
Excellent
·
Apartment
·
1 br
·
Sleeps 4
·
Ocean · Waterfront · Fitness Center ·
From
$220/nightProperty
Apartment · 1 Bed · 1 bath
Amenities
Ocean
Waterfront
Fitness Center
Pool
In Unit Laundry
Wifi
Air Conditioning
Furnished
Other spaces
Kitchen
Steps From Duval St. Historical Charm Meets Modern Design In Old Town Key West
9.9
Excellent
·
House
·
3 br
·
Walk In Closets · Outdoor Space · Private Pool ·
From
$1,363/nightProperty
House · 3 Beds · 3 baths
Amenities
Walk In Closets
Private Pool
Beach
Oven
Dishwasher
Pool
In Unit Laundry
Wifi
Other spaces
Kitchen
**FAIRWAY TO HEAVEN @ THE GOLF CLUB** Lavish Home + LAST KEY SERVICES…
10
Excellent
·
House
·
3 br
·
Sleeps 8
·
Central Heat · Ceiling Fan · Balcony ·
From
$185/nightProperty
House · 3 Beds · 3 baths
Amenities
Central Heat
Ceiling Fan
Dishwasher
Pool
In Unit Laundry
Wifi
Air Conditioning
Furnished
Other spaces
Balcony, Kitchen
2BR Condo - Galleon Resort & Marina - Walk to Mallory Square and Duval Street
10
Excellent
·
Condo
·
2 br
·
Sleeps 6
·
Ocean · Waterfront · Hot Tub ·
From
$546/nightProperty
Condo · 2 Beds · 2 baths
Amenities
Ocean
Waterfront
Hot Tub
Beach
Oven
Dishwasher
Pool
In Unit Laundry
Other spaces
Balcony, Kitchen
Margarita Suite - Bright Condo w/ Pool Access!
10
Excellent
·
Condo
·
2 br
·
Sleeps 6
·
Hot Tub · Assigned Parking · Balcony ·
From
$356/nightProperty
Condo · 2 Beds · 2 baths
Amenities
Hot Tub
Assigned Parking
Oven
Dishwasher
Pool
In Unit Laundry
Wifi
Air Conditioning
Other spaces
Balcony, Kitchen
ISLAND ESCAPE - Old Town Key West w/ Pool & Parking
10
Excellent
·
House
·
2 br
·
Sleeps 4
·
Workspace · On Site Laundry · Assigned Parking ·
From
$350/nightProperty
House · 2 Beds · 2 baths
Amenities
On Site Laundry
Assigned Parking
Private Pool
Oven
Dishwasher
Pool
In Unit Laundry
Wifi
Other spaces
Workspace, Kitchen
2 BEDROOM SUITE - HYATT BEACH HOUSE RESORT - KEY WEST
10
Excellent
·
Hotel
·
2 br
·
On Site Laundry · Beach · Balcony ·
From
$1,666/nightProperty
Hotel · 2 Beds · 2 baths
Amenities
On Site Laundry
Beach
Oven
Dishwasher
Pool
In Unit Laundry
Wifi
Air Conditioning
Other spaces
Balcony, Kitchen
2 BEDROOM SUITE - HYATT SUNSET HARBOR RESORT - KEY WEST, FLORIDA
No reviews
·
Hotel
·
2 br
·
Ceiling Fan · On Site Laundry · Balcony ·
From
$1,765/nightProperty
Hotel · 2 Beds · 2 baths
Amenities
Ceiling Fan
On Site Laundry
Pool
In Unit Laundry
Wifi
Air Conditioning
Furnished
Swimming Pool
Other spaces
Balcony, Kitchen
The best of Zumper, delivered
Be the first to hear about new listings matching your search.
2 BEDROOM SUITE, HYATT BEACH HOUSE RESORT SLEEPS 6
No reviews
·
Hotel
·
2 br
·
Balcony · Oven · Dishwasher ·
From
$1,300/nightProperty
Hotel · 2 Beds · 2 baths
Amenities
Oven
Dishwasher
Pool
In Unit Laundry
Wifi
Air Conditioning
Furnished
Swimming Pool
Other spaces
Balcony, Kitchen
**THE TOASTED COCONUT @ OLD TOWN** Fully Restored + Pool + LAST KEY SERVICES…
9.8
Excellent
·
House
·
3 br
·
Sleeps 8
·
Central Heat · Ceiling Fan · Outdoor Space ·
From
$958/nightProperty
House · 3 Beds · 4 baths
Amenities
Central Heat
Ceiling Fan
Private Pool
Dishwasher
Pool
In Unit Laundry
Wifi
Air Conditioning
Other spaces
Balcony, Kitchen
Tropical Seclusion On Old Town Lane With Pool And Detached Bungalow. Sleeps 6
10
Excellent
·
House
·
3 br
·
Sleeps 6
·
Ceiling Fan · Hot Tub · Outdoor Space ·
From
$363/nightProperty
House · 3 Beds · 3 baths
Amenities
Ceiling Fan
Hot Tub
Fitness Center
Private Pool
Oven
Dishwasher
Pool
In Unit Laundry
Other spaces
Balcony, Kitchen
Dreamworks Conch Cottage
8.9
Very good
·
House
·
2 br
·
Sleeps 4
·
Outdoor Space · Oven · Dishwasher ·
From
$181/nightProperty
House · 2 Beds · 1 bath
Amenities
Oven
Dishwasher
In Unit Laundry
Wifi
Air Conditioning
Furnished
Fitness Center
Residents Lounge
Other spaces
Kitchen
KEY LIME COTTAGE ~ Renovated 3 Bedroom, 2 Bathroom Home with Private Pool!
10
Excellent
·
House
·
3 br
·
Sleeps 6
·
Fitness Center · Private Pool · Beach ·
From
$308/nightProperty
House · 3 Beds · 2 baths
Amenities
Fitness Center
Private Pool
Beach
Oven
Dishwasher
Pool
In Unit Laundry
Wifi
Other spaces
Kitchen
"Frangipani" is a tropical luxurious home in desirable Casa Marina neighborhood.
No reviews
·
House
·
3 br
·
Sleeps 6
·
Walk In Closets · Workspace · High Ceilings ·
From
$550/nightProperty
House · 3 Beds · 4 baths
Amenities
Walk In Closets
High Ceilings
On Site Laundry
Fitness Center
Private Pool
Beach
Oven
Dishwasher
Other spaces
Workspace, Balcony, Kitchen
Amazing Penthouse
9.7
Excellent
·
Condo
·
2 br
·
Sleeps 4
·
Balcony · Dishwasher · Pool ·
From
$716/nightProperty
Condo · 2 Beds · 2 baths
Amenities
Dishwasher
Pool
In Unit Laundry
Wifi
Air Conditioning
Furnished
Swimming Pool
Elevator
Other spaces
Balcony, Kitchen
~ MY HAPPY PLACE ~ A charmingly beautiful treasure in a perfect location!
No reviews
·
House
·
2 br
·
Hardwood Floor · Ceiling Fan · High Ceilings ·
From
$234/nightProperty
House · 2 Beds · 2 baths
Amenities
Hardwood Floor
Ceiling Fan
High Ceilings
Assigned Parking
Fitness Center
Private Pool
Oven
Dishwasher
Other spaces
Kitchen
Eleanor's Place in Key West Old Town - Dogs Ok with Parking.
No reviews
·
House
·
2 br
·
Smoking Allowed · Workspace · Waterfront ·
From
$399/nightProperty
House · 2 Beds · 2 baths
Amenities
Smoking Allowed
Waterfront
Assigned Parking
Beach
Oven
Dishwasher
Pool
In Unit Laundry
Other spaces
Workspace, Balcony, Kitchen
Rent a Piece of Paradise, Best Location on the Island!
9.8
Excellent
·
Condo
·
2 br
·
Sleeps 4
·
Waterfront · Outdoor Space · Beach ·
From
$300/nightProperty
Condo · 2 Beds · 1 bath
Amenities
Waterfront
Beach
Oven
Dishwasher
Pool
In Unit Laundry
Wifi
Air Conditioning
Other spaces
Kitchen
Duval Sq., Old Town, very walkable, full kitchen, pool, parking, 2 BR/2.5 BA.
10
Excellent
·
Condo
·
2 br
·
Sleeps 6
·
Assigned Parking · Balcony · Oven ·
From
$238/nightProperty
Condo · 2 Beds · 3 baths
Amenities
Assigned Parking
Oven
Dishwasher
Pool
In Unit Laundry
Wifi
Air Conditioning
Furnished
Other spaces
Balcony, Kitchen
STARS AND STRIPES ~ Magnificent Home Located In The Heart of Old Town!
9.8
Excellent
·
House
·
8 br
·
Sleeps 20
·
On Site Laundry · Fitness Center · Private Pool ·
From
$1,715/nightProperty
House · 8 Beds · 3 baths
Amenities
On Site Laundry
Fitness Center
Private Pool
Beach
Oven
Dishwasher
Pool
In Unit Laundry
Other spaces
Balcony, Kitchen
CLEAR SKIES ~ Well Appointed 3 Bedroom, 2 Bath Home with Pool!
No reviews
·
House
·
3 br
·
Workspace · Assigned Parking · Fitness Center ·
From
$412/nightProperty
House · 3 Beds · 3 baths
Amenities
Assigned Parking
Fitness Center
Private Pool
Beach
Oven
Dishwasher
Pool
In Unit Laundry
Other spaces
Workspace, Balcony, Kitchen
Pelico Palms Sunset Cottage
No reviews
·
House
·
2 br
·
Sleeps 5
·
Pool · In Unit Laundry · Wifi ·
From
$411/nightProperty
House · 2 Beds · 2 baths
Amenities
Pool
In Unit Laundry
Wifi
Air Conditioning
Furnished
Swimming Pool
Other spaces
Kitchen
Pelico Palms Villa With Treehouse
No reviews
·
House
·
6 br
·
Sleeps 14
·
Oven · Dishwasher · Pool ·
From
$1,546/nightProperty
House · 6 Beds · 6 baths
Amenities
Oven
Dishwasher
Pool
In Unit Laundry
Wifi
Air Conditioning
Furnished
Swimming Pool
Other spaces
Kitchen
Pelico Palms Villa
No reviews
·
House
·
4 br
·
Sleeps 10
·
Outdoor Space · Pool · In Unit Laundry ·
From
$940/nightProperty
House · 4 Beds · 4 baths
Amenities
Pool
In Unit Laundry
Wifi
Air Conditioning
Furnished
Swimming Pool
Other spaces
Kitchen
Pelico Palms Estate.
No reviews
·
House
·
8 br
·
Sleeps 20
·
Balcony · Oven · Dishwasher ·
From
$1,382/nightProperty
House · 8 Beds · 7 baths
Amenities
Oven
Dishwasher
Pool
In Unit Laundry
Wifi
Air Conditioning
Furnished
Swimming Pool
Other spaces
Balcony, Kitchen
A BANANA REPUBLIC in Old Town Key West
No reviews
·
House
·
2 br
·
Sleeps 6
·
On Site Laundry · Private Pool · Oven ·
From
$551/nightProperty
House · 2 Beds · 3 baths
Amenities
On Site Laundry
Private Pool
Oven
Dishwasher
Pool
In Unit Laundry
Air Conditioning
Furnished
Other spaces
Kitchen
WAIT AND SEA ~ Adorable 2 BR, 2 Ba Condo w/ Shared Pool!
10
Excellent
·
Condo
·
2 br
·
Hardwood Floor · High Ceilings · Assigned Parking ·
From
$159/nightProperty
Condo · 2 Beds · 2 baths
Amenities
Hardwood Floor
High Ceilings
Assigned Parking
Fitness Center
Beach
Oven
Dishwasher
Pool
Other spaces
Kitchen
SOUTHARD SUNSET ~ 2 Bedroom Townhome in Truman Annex w/ Shared Pool!
8
Very good
·
Condo
·
2 br
·
Fitness Center · Beach · Oven ·
From
$401/nightProperty
Condo · 2 Beds · 1 bath
Amenities
Fitness Center
Beach
Oven
Dishwasher
Pool
In Unit Laundry
Wifi
Air Conditioning
Other spaces
Kitchen
Keys, Please - Private Pool & 1 Block to Duval
10
Excellent
·
House
·
3 br
·
Sleeps 6
·
Free Parking · Assigned Parking · Private Pool ·
From
$723/nightProperty
House · 3 Beds · 3 baths
Amenities
Free Parking
Assigned Parking
Private Pool
Oven
Dishwasher
Pool
In Unit Laundry
Wifi
Other spaces
Balcony, Kitchen
A Conch Casita at the Key West Golf Club
No reviews
·
Apartment
·
3 br
·
Sleeps 6
·
Pool · In Unit Laundry · Wifi ·
From
$225/nightProperty
Apartment · 3 Beds · 3 baths
Amenities
Pool
In Unit Laundry
Wifi
Air Conditioning
Furnished
Swimming Pool
Fitness Center
Other spaces
Kitchen
Historic Charm, Heart of Old Town, Tropical Paradise, Key West Quaint.
No reviews
·
House
·
3 br
·
Sleeps 6
·
Hot Tub · Oven · Dishwasher ·
From
$211/nightProperty
House · 3 Beds · 2 baths
Amenities
Hot Tub
Oven
Dishwasher
In Unit Laundry
Wifi
Air Conditioning
Furnished
Roof Deck
Other spaces
Kitchen
Havana Moon over Duval
9.5
Excellent
·
Apartment
·
2 br
·
Sleeps 6
·
Deck · Hardwood Floor · High Ceilings ·
From
$671/nightProperty
Apartment · 2 Beds · 2 baths
Amenities
Hardwood Floor
High Ceilings
Private Pool
Beach
Oven
Dishwasher
Pool
In Unit Laundry
Other spaces
Deck, Balcony, Kitchen
The Palms...A beautiful space in the perfect place.
9.9
Excellent
·
Condo
·
2 br
·
Sleeps 4
·
Waterfront · Outdoor Space · Beach ·
From
$319/nightProperty
Condo · 2 Beds · 1 bath
Amenities
Waterfront
Beach
Oven
Dishwasher
Pool
In Unit Laundry
Wifi
Air Conditioning
Other spaces
Balcony, Kitchen
Unique island luxury
No reviews
·
House
·
2 br
·
Sleeps 4
·
Outdoor Space · Fitness Center · Private Pool ·
From
$436/nightProperty
House · 2 Beds · 2 baths
Amenities
Fitness Center
Private Pool
Beach
Oven
Dishwasher
Pool
In Unit Laundry
Wifi
Other spaces
Kitchen
Catch the sunrise at the complex Shoreline & enjoy the best pool in Key West.
9.4
Excellent
·
Condo
·
2 br
·
Sleeps 6
·
Assigned Parking · Balcony · Oven ·
From
$432/nightProperty
Condo · 2 Beds · 2 baths
Amenities
Assigned Parking
Oven
Dishwasher
Pool
In Unit Laundry
Wifi
Air Conditioning
Furnished
Other spaces
Balcony, Kitchen
Delightful Duval St. condo with shared pool and free WiFi - walk to the beach!
No reviews
·
Condo
·
3 br
·
Sleeps 8
·
Ocean · Waterfront · On Site Laundry ·
From
$495/nightProperty
Condo · 3 Beds · 2 baths
Amenities
Ocean
Waterfront
On Site Laundry
Assigned Parking
Oven
Dishwasher
Pool
In Unit Laundry
Other spaces
Balcony, Kitchen
Ocean Hideaway Key West Retreat Private Nature preserve and Ocean views await
8.8
Very good
·
Condo
·
2 br
·
Sleeps 6
·
Hot Tub · Balcony · Oven ·
From
$500/nightProperty
Condo · 2 Beds · 2 baths
Amenities
Hot Tub
Oven
Dishwasher
Pool
In Unit Laundry
Wifi
Air Conditioning
Furnished
Other spaces
Balcony, Kitchen
The LPA Jr. ,1 / 1 Southernmost Point Key West
No reviews
·
Apartment
·
1 br
·
Sleeps 2
·
In Unit Laundry · Wifi · Air Conditioning ·
From
$243/nightProperty
Apartment · 1 Bed · 1 bath
Amenities
In Unit Laundry
Wifi
Air Conditioning
Furnished
Trinidad Suite - Pool View & Private Balcony
9
Excellent
·
Condo
·
2 br
·
Sleeps 6
·
Hot Tub · Assigned Parking · Balcony ·
From
$431/nightProperty
Condo · 2 Beds · 2 baths
Amenities
Hot Tub
Assigned Parking
Oven
Dishwasher
Pool
In Unit Laundry
Wifi
Air Conditioning
Other spaces
Balcony, Kitchen
Duval Balcony - Spanky's Retreat
9.1
Excellent
·
Apartment
·
1 br
·
Sleeps 4
·
Fitness Center · Balcony · In Unit Laundry ·
From
$432/nightProperty
Apartment · 1 Bed · 1 bath
Amenities
Fitness Center
In Unit Laundry
Wifi
Air Conditioning
Furnished
Other spaces
Balcony, Kitchen
Townhouse Suite with 1 Bed, 1 Bath, Kitchen, and Pullout Sofa
10
Excellent
·
House
·
1 br
·
Sleeps 4
·
Hardwood Floor · Ceiling Fan · High Ceilings ·
From
$557/nightProperty
House · 1 Bed · 1 bath
Amenities
Hardwood Floor
Ceiling Fan
High Ceilings
Fitness Center
Beach
Oven
Dishwasher
Pool
Other spaces
Balcony, Kitchen
Classic Dog-Friendly Condo with Shared Pool, Central AC, and High-Speed WiFi
9.3
Excellent
·
Condo
·
2 br
·
Sleeps 6
·
Hot Tub · On Site Laundry · Assigned Parking ·
From
$303/nightProperty
Condo · 2 Beds · 2 baths
Amenities
Hot Tub
On Site Laundry
Assigned Parking
Fitness Center
Oven
Dishwasher
Pool
In Unit Laundry
Other spaces
Balcony, Kitchen
Key West Hemingway House Casa Marina neighborhood
No reviews
·
House
·
3 br
·
Sleeps 6
·
Smoking Allowed · Private Pool · Dishwasher ·
From
$550/nightProperty
House · 3 Beds · 2 baths
Amenities
Smoking Allowed
Private Pool
Dishwasher
Pool
In Unit Laundry
Wifi
Air Conditioning
Furnished
Other spaces
Kitchen
Canalside condo with private dock, boat ramp, water-view patio, central AC & W/D
No reviews
·
House
·
2 br
·
Sleeps 6
·
Ocean · Free Parking · Waterfront ·
From
$142/nightProperty
House · 2 Beds · 2 baths
Amenities
Ocean
Free Parking
Waterfront
On Site Laundry
Beach
Oven
Dishwasher
In Unit Laundry
Other spaces
Balcony, Kitchen
SECOND WIND ~ Charming 2 Bedroom, 2 Bathroom Home w/ Pool!
8
Very good
·
House
·
2 br
·
Sleeps 4
·
Hardwood Floor · High Ceilings · Fitness Center ·
From
$275/nightProperty
House · 2 Beds · 3 baths
Amenities
Hardwood Floor
High Ceilings
Fitness Center
Private Pool
Beach
Oven
Dishwasher
Pool
Other spaces
Kitchen
Ocean views and beach breezes at La Brisa's #303 West
9.3
Excellent
·
Condo
·
2 br
·
Hot Tub · Assigned Parking · Fitness Center ·
From
$193/nightProperty
Condo · 2 Beds · 2 baths
Amenities
Hot Tub
Assigned Parking
Fitness Center
Beach
Oven
Dishwasher
Pool
In Unit Laundry
Other spaces
Balcony, Kitchen
Helen's Hideaway
8
Very good
·
Apartment
·
2 br
·
Sleeps 6
·
Free Parking · Private Pool · Oven ·
From
$1,315/nightProperty
Apartment · 2 Beds · 2 baths
Amenities
Free Parking
Private Pool
Oven
Dishwasher
Pool
Wifi
Air Conditioning
Furnished
Other spaces
Kitchen
Duval Street Suite with pool
8.5
Very good
·
Apartment
·
1 br
·
Sleeps 4
·
Oven · Dishwasher · Pool ·
From
$378/nightProperty
Apartment · 1 Bed · 1 bath
Amenities
Oven
Dishwasher
Pool
Wifi
Air Conditioning
Furnished
Swimming Pool
Other spaces
Kitchen
Duval Street Suite overlooking Duval with parking and pool
No reviews
·
Apartment
·
1 br
·
Sleeps 4
·
Free Parking · Oven · Dishwasher ·
From
$396/nightProperty
Apartment · 1 Bed · 1 bath
Amenities
Free Parking
Oven
Dishwasher
Pool
Wifi
Air Conditioning
Furnished
Swimming Pool
Other spaces
Kitchen
Duval Square Penthouse R19
10
Excellent
·
Apartment
·
2 br
·
Sleeps 6
·
Hot Tub · On Site Laundry · Outdoor Space ·
From
$556/nightProperty
Apartment · 2 Beds · 3 baths
Amenities
Hot Tub
On Site Laundry
Oven
Dishwasher
Pool
In Unit Laundry
Wifi
Air Conditioning
Other spaces
Balcony, Kitchen
Showing 1 - 50 of 1,828 results
Updated: March 22, 2023
Learn about vacation rentals in
Smathers Beach Key West
Explore 1828 vacation rentals near Smathers Beach Key West, Florida. This beach community has lots to offer from sandy beaches to the blue ocean. Use our interactive map to locate Smathers Beach Key West properties on the beach or more inland. Whether you’re looking for a nightly stay, weekend getaway, or week long vacation, we’ve got you covered. Use the date filters at the top to select your travel dates and view availability. The lowest vacation rental price near Smathers Beach Key West is $142 per night and goes up to as much as $1,765 per night.
696 of the vacation rentals near Smathers Beach Key West are
apartments or condos. The average bathroom count for this property type is 2. The median price for these vacation
units is $389 per night. There are
currently 328 vacation units under this
price. 944 of the vacation rentals near Smathers Beach Key West are houses.
The average bathroom count for a vacation house near Smathers Beach Key West is
3. The average price for vacation houses near Smathers Beach Key West is $633 per night. There are 546 vacation homes under this price. The most common
amenities for vacation rentals near Smathers Beach Key West are: furnished, air conditioning, and kitchen. To find vacation properties that might be a good option for large groups or families, use our filters for bedroom count, bathroom count and more.
1 bed rentals
496 available
2 bed rentals
749 available
3 bed rentals
277 available
4+ bed rentals
250 available
Getting around Smathers Beach Key West
Walking
6/10
Grab your reusable bags–many shops and stores are within walking distance.
Car
10/10
Commuting is easy with multiple accessible routes and plenty of parking.
Transit
3/10
There are a few mass transit options within the area.
Points of interest in Smathers Beach Key West
Groceries
7/10
At least one grocery store within a 15-minute walk
Shopping
6/10
Variety of shops within walking distance
Cafes
4/10
Some cafés within walking distance
Restaurants
6/10
Some restaurants within walking distance
Nightlife
4/10
Some bars within walking distance
Smathers Beach Key West Vacation Rentals FAQ
How many Smathers Beach Key West vacation rentals are available?
As of March 22, 2023, there are 1828 Smathers Beach Key West vacation rentals available. Use the filters on Vacations by Zumper to find your next Smathers Beach Key West vacation spot.
Are there vacation rentals near Smathers Beach Key West that have more than 2 bedrooms?
Currently, there are 1276 vacation rentals near Smathers Beach Key West that have more than 2 bedrooms. Check each listing to view photos, pricing, and amenities, and contact the listing manager to begin your next vacation today.
How many Smathers Beach Key West vacation rentals have internet access?
There are currently 1407 Smathers Beach Key West vacation rentals that have internet access. See a full list of property features, photos, pricing, and check availability today.
How many vacation rentals near Smathers Beach Key West have more than 1 bathroom?
Right now, there are 1794 vacation rentals near Smathers Beach Key West that have more than 1 bathroom. View vacation spots and check availability for different properties today.
Are there any pet friendly Smathers Beach Key West vacation rentals?
As of March 22, 2023, there are 644 pet friendly vacation rentals near Smathers Beach Key West. Pet friendly rental policies are managed by the owner. We recommend contacting the listing agent for dog, cat, and other pet policies.
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