4838+ Vacation Rentals Near Smathers Beach |
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Floridarentalvacations - Vacation Rentals in Smathers Beach

Property Image From $435
         

10.0 (187 Reviews)
Condo
MAJESTIC PARADISE @ Truman Annex - Heart of Old Town, Key West
  • Air Conditioner
  • Parking
  • Pool

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Property Image From $563
         

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8.8 (139 Reviews)
Bed & Breakfast
Amsterdam's Curry Mansion Inn
  • Air Conditioner
  • Parking
  • Pet Friendly

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Property Image From $494
         

10.0 (23 Reviews)
House
89 m² House ∙ 2 bedrooms ∙ 6 guests
  • 957 ft² House
  • Air Conditioner
  • Parking
  • Pool

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Property Image From $462
         

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10.0 (5 Reviews)
Cottage
Atlantic Paradise by Avantstay Great Location w/Balcony, Outdoor Dining & Shared Pool & Hot Tub!
  • Air Conditioner
  • Parking
  • Pool

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Property Image From $474
         

10.0 (178 Reviews)
House
Boli Townhouse - Luxury Rental in gated Truman Annex - Saturday to Saturday only
  • Air Conditioner
  • Parking
  • Pool

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Property Image From $258
         

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9.5 (19 Reviews)
House
Old Town Garden Villas
  • Air Conditioner
  • Pool
  • View

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Property Image From $384
         

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10.0 (16 Reviews)
House
89 m² House ∙ 2 bedrooms ∙ 6 guests
  • 960 ft² House
  • Air Conditioner
  • Parking
  • Pool

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Property Image From $421
         

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10.0 (5 Reviews)
House
Parrot Perch by Avantstay Old Town Key West w/Shared Pool Week Long Stays Only
  • Air Conditioner
  • Parking
  • Pool

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Property Image From $2,070
         

10.0 (141 Reviews)
House
NEW PRICING: DRIVE TO YOUR GETAWAY - BIG Pool, Steps to Beach & Free Parking
  • Air Conditioner
  • Parking
  • Pool

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Property Image From $277
         

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10.0 (1 Review)
House
Casa Tranquility by Brightwild
  • Air Conditioner
  • Parking
  • Internet

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Property Image From $546
         

10.0 (15 Reviews)
House
117 m² House ∙ 2 bedrooms ∙ 5 guests
  • 1259 ft² House
  • Air Conditioner
  • Pool
  • TV

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Property Image From $2,792
         

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10.0 (1 Review)
Apartment
Sunnyside Up by Brightwild Pool Parking
  • Parking
  • Pet Friendly
  • Pool

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Property Image From $371
         

9.8 (157 Reviews)
Condo
Beach House- Ocean & Beach View-Upgraded-Over 146 Five Star Reviews
  • Air Conditioner
  • Parking
  • Pool

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Property Image From $244
         

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New
House
Sunshine Corner
  • Air Conditioner
  • Parking
  • Balcony/Terrace

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Property Image From $1,258
         

9.8 (130 Reviews)
House
Luxury 3-Bedroom Waterfront Home with Pool AND Dock!
  • Air Conditioner
  • Parking
  • Pet Friendly

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Property Image From $238
         

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New
House
Green Mermaid
  • Air Conditioner
  • Pet Friendly
  • Child Friendly

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Property Image From $1,197
         

9.8 (120 Reviews)
House
Conch style home in Oldtown with private pool AND dock!
  • Air Conditioner
  • Parking
  • Pool

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Property Image From $159
         

New
Apartment
Great Old Town Location, Steps from Mallory Square
  • Air Conditioner
  • Internet

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Property Image From $458
         

9.8 (92 Reviews)
House
CASA DE VINO ~ Amazing Price for Charming Townhouse with Pool & Tiki!
  • Air Conditioner
  • Parking
  • Pool

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Property Image From $225
         

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7.3 (3 Reviews)
House
Point Break Suites
  • Air Conditioner
  • Parking
  • Pool

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Property Image From $711
         

9.6 (213 Reviews)
House
PET FRIENDLY! SUMMER SPECIALS ! 3 Bedroom 3 bathroom home. Sleeps 8
  • Air Conditioner
  • Parking
  • Pet Friendly

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Property Image From $887
         

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10.0 (4 Reviews)
House
Mar Y Sol Ocean Front
  • Parking
  • Accessibility
  • Security/Safety

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Property Image From $1,932
         

9.6 (75 Reviews)
House
STARS AND STRIPES ~ Magnificent Home Located In The Heart of Old Town!
  • Air Conditioner
  • Parking
  • Pool

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Property Image From $436
         

10.0 (118 Reviews)
House
Prime location, stunning views from 2 decks—walk or ride to explore the island!
  • Air Conditioner
  • Parking
  • Pool

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★ Pro Tip: Floridarentalvacations makes it easy to compare the best listings on Floridarentalvacations homes from online vacation rental OTAs, including Booking.com and more. Use the Advanced Filter feature at the top to easily flip between Floridarentalvacations 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

Floridarentalvacations 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