Owner Direct Vacation Rentals in Siesta Key

The Best Owner Direct Vacation Rentals in Siesta Key. Explore thousands of vacation home rentals, large cabins, and villas near Siesta Key

323 Canal Rd - Siesta Key Village Condo From US $302
         

The Inn On Siesta Key From US $331
         

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10.0 (192 Reviews)
Cottage
  • Air Conditioner
  • Parking
  • Pet Friendly
One-of-a-kindBeach, Village, Dock & Private Pool! From US $729
         

Luxury Places to Stay in Siesta Key

Over 5754+ Luxury Places to Stay in or Near Siesta Key
Salty Sun Sets Estate From US $6,447
         

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New
House
  • Air Conditioner
  • Parking
  • Pet Friendly
New-Vacationers Paradise-2 Luxury Homes-Sleeps 36 From US $6,283
         

10.0 (2 Reviews)
House
  • Air Conditioner
  • Parking
  • Pet Friendly
New - Luxury 2-Home Estate-Pools & Rooftops From US $5,860
         

Top-Rated Vacation Rentals with a Pool in Siesta Key

Over 4589+ Top-Rated Vacation Rentals with a Pool in or Near Siesta Key
A Bayside Treasure - Outstanding Waterfront Views! From US $241
         

10.0 (209 Reviews)
Condo
  • Air Conditioner
  • Parking
  • Pool
Full Gulf Views Across from Siesta Key Beach From US $305
         

10.0 (179 Reviews)
Condo
  • Air Conditioner
  • Parking
  • Pool
🦩Book Me Baby! Bayview Beauty at Siesta Key 🦩 From US $361
         

10.0 (171 Reviews)
Condo
  • Air Conditioner
  • Parking
  • Pool

Pet-Friendly Vacation Rentals in Siesta Key

Over 1005+ Pet-Friendly Vacation Rentals in or Near Siesta Key
Casa Coquina - 1038U From US $1,759
         

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10.0 (3 Reviews)
House
  • Parking
  • Pet Friendly
  • Pool
Villa Castile - 5204 From US $529
         

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10.0 (3 Reviews)
House
  • Parking
  • Pet Friendly
  • Pool
Seahorse Cabana - 1106 From US $931
         

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10.0 (2 Reviews)
House
  • Parking
  • Pet Friendly
  • Pool

Large Vacation Homes & Villas in Siesta Key

Over 974+ Large Vacation Homes & Villas in or Near Siesta Key
Fiesta Playa - 1027 From US $1,196
         

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10.0 (3 Reviews)
House
  • Parking
  • Pool
  • Accessibility
3-BR with Pool & hot tub From US $694
         

8.8 (12 Reviews)
House
  • Air Conditioner
  • Parking
  • Pet Friendly
Crystal Sands By Beachside Management From US $724
         

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10.0 (2 Reviews)
Apartment
  • Parking
  • Security/Safety
  • Child Friendly
In the Heart of Siesta Key Village and Steps to the #1 Beach From US $480
         

The Conch From US $3,703
         

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10.0 (1 Review)
House
  • Parking
  • Pet Friendly
  • Pool

Wheelchair Accessible Vacation Homes in Siesta Key

Over 1818+ Wheelchair Accessible Vacation Homes in or Near Siesta Key
Siesta Key From US $392
         

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10.0 (6 Reviews)
Apartment
  • Air Conditioner
  • Parking
  • Pool
Available for Season! Tequila Sunrise on Siesta Key From US $171
         

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9.7 (3 Reviews)
Apartment
  • Air Conditioner
  • Parking
  • View
Tropical Beach Resorts - Sarasota From US $236
         

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9.1 (1686 Reviews)
Resort
  • Air Conditioner
  • Parking
  • Pool

Siesta Key Varoom and Airbnb Places to Stay Under $200

Over 437+ Siesta Key Varoom and Airbnb Places to Stay Under $200
Siesta Key Beach - Tropea 665 #3 From US $197
         

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9.8 (22 Reviews)
House
  • Air Conditioner
  • Parking
  • View
Absolutely Affordable at Bay Oaks in Siesta Key
New
From US $180
         

New
Condo
  • Air Conditioner
  • Security/Safety
  • Bedding/Linens
Captiva Beach Resort From US $171
         

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9.0 (1174 Reviews)
Condo
  • Air Conditioner
  • Parking
  • Pool
Breezy Siesta Key Condo with Bay Views and Pool! From US $169
         

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9.5 (4 Reviews)
Apartment
  • Parking
  • Pool
  • Accessibility
A few steps from the beach with community pool From US $189
         

Beautiful, Affordable, Close to famous Siesta Beach. From US $195
         

Harbor Tower Intracoastal Condo From US $174
         

9.5 (2 Reviews)
House
  • Pool
  • View
  • Accessibility

Instantly Bookable Vacation Homes in Siesta Key

Over 3759+ Instantly Bookable Vacation Homes in or Near Siesta Key
Gulf and Bay Club-C607
New
From US $478
         

New
Condo
  • Air Conditioner
  • Parking
  • Pool

About Siesta Key Vacation Rentals

With more than 5763 Siesta Key vacation rentals, we can help you find a place to stay. These rentals, including vacation rentals, Ownerdirect and other short-term private accommodations, have top-notch amenities with the best value, providing you with comfort and luxury at the same time. Get more value and more room when you stay at a rental property in Siesta Key.

Looking for last-minute deals, or finding the best deals available for cottages, condos, private villas, and large vacation homes? With Ownerdirect Siesta Key, you have the flexibility of comparing different options of various deals with a single click. Looking for a rental by owner with the best swimming pools, hot tubs, allows pets, or even those with huge master suite bedrooms and have large screen televisions? You can find vacation rentals by owner, and other popular Airbnb-style properties in Siesta Key. Places to stay near Siesta Key are 971.09 ft² on average, with prices averaging $586 a night.

Ownerdirect makes it easy and safe to find and compare vacation rentals in Siesta Key with prices often at a 30-40% discount versus the price of a hotel. Just search for your destination and secure your reservation today.

Top Rental Accommodation Types in Siesta Key

Type Count
Vacation Homes 1741
Holiday Apartments 558
Villas 373
Cottages 58
Hotels with Suites 29
Ski Chalet Rentals 15
Resorts 11
Others 1

Use these Quick Filters to Find a Vacation Rental in Siesta Key

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

Weather in Siesta Key

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

December - February
High 79°F       Low 51°F
March - May
High 91°F       Low 53°F
June - August
High 92°F       Low 72°F
September - November
High 90°F       Low 57°F