344+ Vacation Rentals Near Smathers Beach |
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  3. Key West
  4. Smathers Beach

Unplugged Weekend - Vacation Rentals in Smathers Beach

Fleming-O From US $583
         

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10.0 (2 Reviews)
House
Fleming-O
  • Air Conditioner
  • Parking
  • View

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Opal Key Resort & Marina, Key West From US $330
         

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9.2 (1184 Reviews)
Hotel
Opal Key Resort & Marina, Key West
  • Air Conditioner
  • Parking
  • Pool

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Beach House- Ocean & Beach View-Upgraded-Over 146 Five Star Reviews From US $249
         

9.6 (168 Reviews)
Condo
Beach House- Ocean & Beach View-Upgraded-Over 146 Five Star Reviews
  • Air Conditioner
  • Parking
  • Pool

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Duke of Catherine by Last Key Realty From US $1,747
         

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10.0 (1 Review)
House
Duke of Catherine by Last Key Realty
  • Parking
  • Pet Friendly
  • Pool

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Ocean Key Resort - A Noble House Resort From US $325
         

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9.2 (1007 Reviews)
Resort
Ocean Key Resort - A Noble House Resort
  • Air Conditioner
  • Parking
  • Pool

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*FOLLOW THE SUN* Ocean Condo/Pool & Tennis + Last Key White Glove Service. From US $494
         

10.0 (164 Reviews)
Condo
*FOLLOW THE SUN* Ocean Condo/Pool & Tennis + Last Key White Glove Service.
  • Air Conditioner
  • Parking
  • Pool

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Casa Serendipity by Last Key Realty From US $1,360
         

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10.0 (1 Review)
House
Casa Serendipity by Last Key Realty
  • Parking
  • Pet Friendly
  • Pool

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*ATLANTIC REFLECTIONS @ THE BEACH* Penthouse + Last Key White Glove Service. From US $599
         

10.0 (128 Reviews)
Condo
*ATLANTIC REFLECTIONS @ THE BEACH* Penthouse + Last Key White Glove Service.
  • Air Conditioner
  • Parking
  • Pool

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*CONCH IN THE TREETOPS* Beach Condo/Pool + Last Key White Glove Service. From US $487
         

9.8 (186 Reviews)
Condo
*CONCH IN THE TREETOPS* Beach Condo/Pool + Last Key White Glove Service.
  • Air Conditioner
  • Parking
  • Pool

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*NATURES EDGE* Ocean Condo/Pool & Tennis + Last Key White Glove Service. From US $493
         

9.8 (170 Reviews)
Condo
*NATURES EDGE* Ocean Condo/Pool & Tennis + Last Key White Glove Service.
  • Air Conditioner
  • Parking
  • Pool

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*NEPTUNE'S PENTHOUSE* Oceanside Condo/Pool + Last Key White Glove Service. From US $654
         

9.8 (128 Reviews)
Condo
*NEPTUNE'S PENTHOUSE* Oceanside Condo/Pool + Last Key White Glove Service.
  • Air Conditioner
  • Parking
  • Pool

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Anchor Drop modern elegance upgrades throughout views of Atlantic Ocean From US $528
         

9.6 (154 Reviews)
Condo
Anchor Drop modern elegance upgrades throughout views of Atlantic Ocean
  • Air Conditioner
  • Parking
  • Pool

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Top floor Ocean Views, Spacious 2 Bedroom Condo, Views from every room From US $505
         

9.2 (128 Reviews)
Condo
Top floor Ocean Views, Spacious 2 Bedroom Condo, Views from every room
  • Air Conditioner
  • Parking
  • Pool

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GATED OCEANFRONT CONDO AT SMATHER'S BEACH From US $498
         

9.2 (152 Reviews)
Condo
GATED OCEANFRONT CONDO AT SMATHER'S BEACH
  • Air Conditioner
  • Parking
  • Pool

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Mar Y Sol –Luxurious oceanfront Key West Breathtaking Atlantic Sunrise Views From US $709
         

9.2 (168 Reviews)
Condo
Mar Y Sol –Luxurious oceanfront Key West Breathtaking Atlantic Sunrise Views
  • Air Conditioner
  • Parking
  • Pool

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Frost Free at 1800 Atlantic overlooking Smathers Beach top and the sunrise From US $446
         

9.2 (153 Reviews)
Condo
Frost Free at 1800 Atlantic overlooking Smathers Beach top and the sunrise
  • Air Conditioner
  • Parking
  • Pool

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Atlantic Paradise Found modern luxury Best pool in Key West fine finishes From US $488
         

9.4 (145 Reviews)
Condo
Atlantic Paradise Found modern luxury Best pool in Key West fine finishes
  • Air Conditioner
  • Parking
  • Pool

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Key Wes't Best- Upgraded condo 5 mins to Smathers Beach Fantastic value From US $406
         

9.4 (147 Reviews)
Condo
Key Wes't Best- Upgraded condo 5 mins to Smathers Beach Fantastic value
  • Air Conditioner
  • Parking
  • Pool

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Botanical Island Delight Key West fantastic discounts for Summer & Fall From US $478
         

9.0 (155 Reviews)
Condo
Botanical Island Delight Key West fantastic discounts for Summer & Fall
  • Air Conditioner
  • Parking
  • Pool

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Premier Ocean views, expansive balcony, renovated kitchen & bath 2024 From US $492
         

8.8 (102 Reviews)
Condo
Premier Ocean views, expansive balcony, renovated kitchen & bath 2024
  • Air Conditioner
  • Parking
  • Pool

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Key West On My Mind, Ocean Views, Renovated Kitchen, Last minute deals From US $482
         

9.0 (69 Reviews)
Condo
Key West On My Mind, Ocean Views, Renovated Kitchen, Last minute deals
  • Air Conditioner
  • Parking
  • Pool

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Carolina to Keys Ocean view dream Monthly pricing Best pool on the Island From US $1,277
         

9.8 (15 Reviews)
Condo
Carolina to Keys Ocean view dream Monthly pricing Best pool on the Island
  • Air Conditioner
  • Parking
  • Pool

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Sea La Vie, Elegant Key West 2BR/2BA | Renovated Condo at 1800 Atlantic From US $265
         

9.2 (10 Reviews)
Condo
Sea La Vie, Elegant Key West 2BR/2BA | Renovated Condo at 1800 Atlantic
  • Air Conditioner
  • Parking
  • Pool

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Key West Beachfront Luxury 2/2 Condo A212 From US $570
         

10.0 (172 Reviews)
Condo
Key West Beachfront Luxury 2/2 Condo A212
  • Air Conditioner
  • Parking
  • Pool

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★ Pro Tip: Unpluggedweekend makes it easy to compare the best listings on Unpluggedweekend homes from online vacation rental OTAs, including Booking.com and more. Use the Advanced Filter feature at the top to easily flip between Unpluggedweekend homes, vacation rentals, bed and breakfasts, private Airbnb-style rentals availability, eco-friendly properties, property type, cancellation policies, prices, and several different options. All these make it easier to find the perfect accommodation for your next vacation in Smathers Beach.

Weather in Smathers Beach

View the weather forecast for Smathers Beach before booking your Smathers Beach Vacation Rentals to confirm your best time to go.

December - February
High 81°F       Low 67°F
March - May
High 87°F       Low 70°F
June - August
High 91°F       Low 80°F
September - November
High 90°F       Low 73°F

Top Attractions Around Smathers Beach, FL

Unpluggedweekend offers a large selection of top attractions around Smathers Beach. Research things to do on your vacation before you visit Smathers Beach.


Duval Street Southernmost Point Mallory Square South Beach Higgs Beach Key West Harbour Key West Aquarium Ernest Hemingway Home and Museum Fort Zachary Taylor Historic State Park Key West Butterfly and Nature Conservatory Florida Keys Beaches Saddlebunch Keys Harry S. Truman Little White House Key West Shipwreck Museum Key West Golf Club Key West Lighthouse and Keeper's Quarters Museum Ripley's Believe It or Not Audubon House and Tropical Gardens Florida Keys National Marine Sanctuary

Smathers Beach Vacation Rental Frequently Asked Questions

What are the top vacation rentals in Smathers Beach?

There are a lot of options in Smathers Beach. If you plan on staying in the Smathers Beach area, consider making a reservation for a few nights at one of these properties as these have been rated the Top Vacation Rentals in Smathers Beach:

How many vacation rentals are available in Smathers Beach?

Currently, the total number of properties listed in 2026 is over 344 in the Smathers Beach area, and still counting. By aggregating listings from multiple websites, offers an immense amount of choice of the best properties in Smathers Beach.