329+ Vacation Rentals Near Simonton Beach |
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Unplugged Weekend - Vacation Rentals in Simonton Beach

Beach House- Ocean & Beach View-Upgraded-Over 146 Five Star Reviews From US $315
         

9.8 (165 Reviews)
Condo
Beach House- Ocean & Beach View-Upgraded-Over 146 Five Star Reviews
  • Air Conditioner
  • Parking
  • Pool

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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 (1171 Reviews)
Hotel
Opal Key Resort & Marina, Key West
  • Air Conditioner
  • Parking
  • Pool

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*FOLLOW THE SUN @ THE BEACH* Ocean Condo/Pool & Tennis + LAST KEY SERVICES. From US $490
         

10.0 (162 Reviews)
Condo
*FOLLOW THE SUN @ THE BEACH* Ocean Condo/Pool & Tennis + LAST KEY SERVICES.
  • 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 $492
         

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9.2 (1003 Reviews)
Resort
Ocean Key Resort - A Noble House Resort
  • Air Conditioner
  • Parking
  • Pool

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*ATLANTIC REFLECTIONS @ THE BEACH* Ocean Penthouse/Pool + LAST KEY SERVICES. From US $610
         

10.0 (128 Reviews)
Condo
*ATLANTIC REFLECTIONS @ THE BEACH* Ocean Penthouse/Pool + LAST KEY SERVICES.
  • 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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*CONCH IN THE TREETOPS @ 1800 ATLANTIC* Beach Condo/Pool + LAST KEY SERVICES From US $492
         

9.8 (186 Reviews)
Condo
*CONCH IN THE TREETOPS @ 1800 ATLANTIC* Beach Condo/Pool + LAST KEY SERVICES
  • Air Conditioner
  • Parking
  • Pool

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*NATURES EDGE @ THE BEACH* Ocean Condo/Pool & Tennis + LAST KEY SERVICES. From US $492
         

9.8 (166 Reviews)
Condo
*NATURES EDGE @ THE BEACH* Ocean Condo/Pool & Tennis + LAST KEY SERVICES.
  • Air Conditioner
  • Parking
  • Pool

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*NEPTUNE'S PENTHOUSE @ THE BEACH* Oceanfront Condo/Pool + LAST KEY SERVICE. From US $658
         

9.8 (127 Reviews)
Condo
*NEPTUNE'S PENTHOUSE @ THE BEACH* Oceanfront Condo/Pool + LAST KEY SERVICE.
  • Air Conditioner
  • Parking
  • Pool

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Anchor Drop modern elegance upgrades throughout views of Atlantic Ocean From US $506
         

9.6 (151 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 $502
         

9.2 (127 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 $493
         

9.2 (151 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 $695
         

9.2 (166 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 $450
         

9.2 (150 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 $548
         

9.4 (143 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 $430
         

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 $422
         

9.0 (151 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 $495
         

8.8 (101 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 $455
         

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 $1,235
         

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 $295
         

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 $663
         

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 Simonton Beach.

Weather in Simonton Beach

View the weather forecast for Simonton Beach before booking your Simonton 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 Simonton Beach, FL

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


Duval Street Smathers Beach 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

Simonton Beach Vacation Rental Frequently Asked Questions

What are the top vacation rentals in Simonton Beach?

There are a lot of options in Simonton Beach. If you plan on staying in the Simonton 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 Simonton Beach:

How many vacation rentals are available in Simonton Beach?

Currently, the total number of properties listed in 2026 is over 329 in the Simonton Beach area, and still counting. By aggregating listings from multiple websites, offers an immense amount of choice of the best properties in Simonton Beach.