Luxury Home Villas - Vacation Rentals in Siesta Key

Island House Beach Resort V36 From US $439
         

9.0 (18 Reviews)
Villa
  • Air Conditioner
  • Pool
  • TV
Island House Beach Resort 1 From US $324
         

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10.0 (1 Review)
Villa
  • Air Conditioner
  • Pool
  • Child Friendly
Miramar From US $2,611
         

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New
Villa
  • Air Conditioner
  • TV
  • Wheelchair Accessible
Island House Beach Resort V11 From US $399
         

9.6 (17 Reviews)
Villa
  • Air Conditioner
  • Pool
  • TV
Island House Beach Resort V24 From US $436
         

9.6 (19 Reviews)
Villa
  • Air Conditioner
  • Parking
  • Pool
Crystal Sands Villa 12 - Private Beach From US $260
         

10.0 (2 Reviews)
Villa
  • Air Conditioner
  • Parking
  • Pool
Island House Beach Resort V28 From US $436
         

9.8 (21 Reviews)
Villa
  • Air Conditioner
  • Pool
  • Balcony/Terrace

Luxury Places to Stay in Siesta Key

Over 6053+ Luxury Places to Stay in or Near Siesta Key
New - Luxury 2-Home Estate-Pools & Rooftops From US $12,843
         

New-Vacationers Paradise-2 Luxury Homes-Sleeps 36 From US $8,926
         

10.0 (2 Reviews)
House
  • Air Conditioner
  • Parking
  • Pet Friendly

Top-Rated Vacation Rentals with a Pool in Siesta Key

Over 4779+ Top-Rated Vacation Rentals with a Pool in or Near Siesta Key
A Bayside Treasure - Outstanding Waterfront Views! From US $241
         

10.0 (214 Reviews)
Condo
  • Air Conditioner
  • Parking
  • Pool
The Inn On Siesta Key From US $387
         

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10.0 (198 Reviews)
Cottage
  • Air Conditioner
  • Parking
  • Pet Friendly
Full Gulf Views Across from Siesta Key Beach From US $306
         

10.0 (183 Reviews)
Condo
  • Air Conditioner
  • Parking
  • Pool
🦩Book Me Baby! Bayview Beauty at Siesta Key 🦩 From US $231
         

10.0 (172 Reviews)
Condo
  • Air Conditioner
  • Parking
  • Pool

Pet-Friendly Vacation Rentals in Siesta Key

Over 1058+ Pet-Friendly Vacation Rentals in or Near Siesta Key
Across The Street From #1 Beach From US $294
         

10.0 (329 Reviews)
Cottage
  • Air Conditioner
  • Parking
  • Pet Friendly
323 Canal Rd - Siesta Key Village Condo From US $302
         

Large Vacation Homes & Villas in Siesta Key

Over 1047+ Large Vacation Homes & Villas in or Near Siesta Key
Siesta Key Retreat Sarasota Florida From US $1,408
         

9.8 (46 Reviews)
House
  • Air Conditioner
  • Parking
  • Pool
Island House Beach Resort 23 From US $378
         

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New
Villa
  • Air Conditioner
  • Pool
  • Child Friendly
Pet Friendly Home on Siesta Key w/Private Heated Pool & Putting Green From US $669
         

Siesta Home with Pool & Waterslide - Sunset Splash From US $1,909
         

10.0 (74 Reviews)
House
  • Air Conditioner
  • Parking
  • Pet Friendly

Wheelchair Accessible Vacation Homes in Siesta Key

Over 1992+ Wheelchair Accessible Vacation Homes in or Near Siesta Key
Sandy Shore 5157 From US $173
         

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New
House
  • Parking
  • Pool
  • Wheelchair Accessible
Little slice of paradise, Siesta Dunes 2-209. From US $536
         

10.0 (22 Reviews)
Condo
  • Air Conditioner
  • Parking
  • Pool
Siesta Key From US $392
         

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10.0 (6 Reviews)
Apartment
  • Air Conditioner
  • Parking
  • Pool
Exceptional Beachfront condo on Crescent Beach From US $427
         

10.0 (119 Reviews)
Condo
  • Air Conditioner
  • Parking
  • Pool
Siesta Key For Me @ The Palm Bay Club From US $386
         

10.0 (111 Reviews)
Condo
  • Air Conditioner
  • Parking
  • Pool

Siesta Key Vacation Rentals and Airbnb Places to Stay Under $200

Over 513+ Siesta Key Vacation Rentals and Airbnb Places to Stay Under $200
Siesta Bayside Closest to the Beach From US $185
         

Relaxing Siesta Key Condo From US $197
         

9.6 (44 Reviews)
Condo
  • Air Conditioner
  • Parking
  • Pool
Barb's Three Wishes.Sun, Sand, Siesta! From US $187
         

9.8 (96 Reviews)
Condo
  • Air Conditioner
  • Parking
  • Pool
Siesta Key 2 Bedroom Condo From US $170
         

9.4 (54 Reviews)
Condo
  • Air Conditioner
  • Parking
  • Pool

Instantly Bookable Vacation Homes in Siesta Key

Over 3985+ Instantly Bookable Vacation Homes in or Near Siesta Key
Amazing 1 Br/1 Ba Condo at Casa Mar From US $396
         

9.8 (170 Reviews)
Condo
  • Air Conditioner
  • Parking
  • Pool
Renovated condo with easy beach access on Siesta From US $215
         

About Siesta Key Vacation Rentals

With more than 490 Siesta Key vacation rentals, we can help you find a place to stay. These rentals, including vacation rentals, Luxuryhomevilla 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 Luxuryhomevilla 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 421.67 ft² on average, with prices averaging US $421 a night.

Luxuryhomevilla 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
Villas 425
Vacation Homes 56
Holiday Apartments 9

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

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

Siesta Key Vacation Rental Frequently Asked Questions

What are the top vacation rentals in Siesta Key?
How many vacation rentals are available in Siesta Key?

Currently, the total number of properties listed in 2026 is over 490 in the Siesta Key area, and still counting. By aggregating listings from multiple websites, offers an immense amount of choice of the best properties in Siesta Key.