The Islands Advisors - Vacation Rentals in Siesta Key Village

Across The Street From #1 Beach From US $294
         

10.0 (329 Reviews)
Cottage
  • Air Conditioner
  • Parking
  • Pet Friendly
The Inn On Siesta Key From US $492
         

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10.0 (195 Reviews)
Cottage
  • Air Conditioner
  • Parking
  • Pet Friendly
A Bayside Treasure - Outstanding Waterfront Views! From US $241
         

10.0 (212 Reviews)
Condo
  • Air Conditioner
  • Parking
  • Pool
Little slice of paradise, Siesta Dunes 2-209. From US $536
         

10.0 (22 Reviews)
Condo
  • Air Conditioner
  • Parking
  • Pool

Luxury Places to Stay in Siesta Key Village

Over 5773+ Luxury Places to Stay in or Near Siesta Key Village
New-Vacationers Paradise-2 Luxury Homes-Sleeps 36 From US $9,433
         

10.0 (2 Reviews)
House
  • Air Conditioner
  • Parking
  • Pet Friendly
Gulfside Green Estate From US $6,470
         

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New
House
  • Air Conditioner
  • Parking
  • Pet Friendly
Salty Sun Sets Estate From US $6,447
         

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New
House
  • Air Conditioner
  • Parking
  • Pet Friendly

Top-Rated Vacation Rentals with a Pool in Siesta Key Village

Over 4572+ Top-Rated Vacation Rentals with a Pool in or Near Siesta Key Village
Full Gulf Views Across from Siesta Key Beach From US $306
         

10.0 (182 Reviews)
Condo
  • Air Conditioner
  • Parking
  • Pool
🦩Book Me Baby! Bayview Beauty at Siesta Key 🦩 From US $263
         

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

Pet-Friendly Vacation Rentals in Siesta Key Village

Over 1008+ Pet-Friendly Vacation Rentals in or Near Siesta Key Village
323 Canal Rd - Siesta Key Village Condo From US $302
         

Large Vacation Homes & Villas in Siesta Key Village

Over 952+ Large Vacation Homes & Villas in or Near Siesta Key Village
Siesta Key Retreat Sarasota Florida From US $1,408
         

9.8 (46 Reviews)
House
  • Air Conditioner
  • Parking
  • Pool
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 V36 From US $516
         

9.0 (18 Reviews)
Villa
  • Air Conditioner
  • Pool
  • TV
Island House Beach Resort V11 From US $536
         

9.6 (16 Reviews)
Villa
  • Air Conditioner
  • Pool
  • TV

Wheelchair Accessible Vacation Homes in Siesta Key Village

Over 1971+ Wheelchair Accessible Vacation Homes in or Near Siesta Key Village
Siesta Key For Me @ The Palm Bay Club From US $400
         

10.0 (110 Reviews)
Condo
  • Air Conditioner
  • Parking
  • Pool
Sandy Shore 5157 From US $173
         

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New
House
  • Parking
  • Pool
  • Wheelchair Accessible
Siesta Key From US $392
         

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10.0 (6 Reviews)
Apartment
  • Air Conditioner
  • Parking
  • Pool
Island House Beach Resort 15S From US $681
         

10.0 (31 Reviews)
Apartment
  • Air Conditioner
  • Parking
  • Pool

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

Over 468+ Siesta Key Village Vacation Rentals and Airbnb Places to Stay Under $200
Relaxing Siesta Key Condo From US $197
         

9.6 (43 Reviews)
Condo
  • Air Conditioner
  • Parking
  • Pool
Siesta Bayside Closest to the Beach From US $185
         

Barb's Three Wishes.Sun, Sand, Siesta! From US $187
         

9.8 (95 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 Village

Over 3846+ Instantly Bookable Vacation Homes in or Near Siesta Key Village
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 $468
         

About Siesta Key Village Vacation Rentals

With more than 5782 Siesta Key Village vacation rentals, we can help you find a place to stay. These rentals, including vacation rentals, Theislandsadvisors 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 Village.

Looking for last-minute deals, or finding the best deals available for cottages, condos, private villas, and large vacation homes? With Theislandsadvisors Siesta Key Village, 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 Village. Places to stay near Siesta Key Village are 960.1 ft² on average, with prices averaging $574 a night.

Theislandsadvisors makes it easy and safe to find and compare vacation rentals in Siesta Key Village 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 Village

Type Count
Vacation Homes 1602
Holiday Apartments 570
Villas 361
Cottages 63
Hotels with Suites 31
Ski Chalet Rentals 15
Resorts 12
Others 1

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

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

Weather in Siesta Key Village

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

December - February
High 60°F       Low 26°F
March - May
High 77°F       Low 40°F
June - August
High 91°F       Low 64°F
September - November
High 84°F       Low 38°F

Other Places to Stay Near Siesta Key Village, FL


Siesta Key Village Vacation Rental Frequently Asked Questions

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

Currently, the total number of properties listed in 2026 is over 5782 in the Siesta Key Village area, and still counting. By aggregating listings from multiple websites, offers an immense amount of choice of the best properties in Siesta Key Village.