Luxury Cruises - Vacation Rentals in Siesta Key

Property Image From $274
         

10.0 (321 Reviews)
Cottage
  • Air Conditioner
  • Parking
  • Pet Friendly
Property Image From $246
         

10.0 (123 Reviews)
House
  • 1300 ft² House
  • Air Conditioner
  • Parking
  • Pool
Property Image From $249
         

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10.0 (184 Reviews)
Cottage
  • Air Conditioner
  • Parking
  • Pet Friendly
Property Image From $241
         

10.0 (208 Reviews)
Condo
  • Air Conditioner
  • Parking
  • Pool
Property Image From $173
         

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New
House
  • Parking
  • Pool
  • Wheelchair Accessible
Property Image From $324
         

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10.0 (1 Review)
Villa
  • Air Conditioner
  • Pool
  • Child Friendly

Luxury Places to Stay in Siesta Key

Over 6046+ Luxury Places to Stay in or Near Siesta Key
Property Image From $5,989
         

9.6 (17 Reviews)
House
  • Air Conditioner
  • Parking
  • Pet Friendly
Property Image From $5,381
         

New
House
  • Air Conditioner
  • Parking
  • Pet Friendly
Property Image From $5,027
         

New
House
  • Air Conditioner
  • Parking
  • Pool
Property Image From $4,838
         

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New
House
  • Parking
  • Pet Friendly
  • Pool

Top-Rated Vacation Rentals with a Pool in Siesta Key

Over 4825+ Top-Rated Vacation Rentals with a Pool in or Near Siesta Key
Property Image From $300
         

10.0 (178 Reviews)
Condo
  • Air Conditioner
  • Parking
  • Pool
Property Image From $210
         

10.0 (170 Reviews)
Condo
  • Air Conditioner
  • Parking
  • Pool
Property Image From $492
         

Pet-Friendly Vacation Rentals in Siesta Key

Over 1099+ Pet-Friendly Vacation Rentals in or Near Siesta Key
Property Image From $302
         

Property Image From $599
         

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10.0 (53 Reviews)
House
  • 1670 ft² House
  • Air Conditioner
  • Parking
  • Pet Friendly
Property Image From $2,572
         

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10.0 (3 Reviews)
House
  • Parking
  • Pet Friendly
  • Pool
Property Image From $1,759
         

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10.0 (3 Reviews)
House
  • Parking
  • Pet Friendly
  • Pool

Large Vacation Homes & Villas in Siesta Key

Over 1113+ Large Vacation Homes & Villas in or Near Siesta Key
Property Image From $1,574
         

10.0 (41 Reviews)
House
  • Air Conditioner
  • Parking
  • Pool
Property Image From $378
         

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New
Villa
  • Air Conditioner
  • Pool
  • Child Friendly
Property Image From $656
         

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10.0 (48 Reviews)
House
  • 1999 ft² House
  • Air Conditioner
  • Parking
  • Pet Friendly
Property Image From $729
         

Property Image From $1,196
         

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10.0 (3 Reviews)
House
  • Parking
  • Pool
  • Accessibility

Wheelchair Accessible Vacation Homes in Siesta Key

Over 1776+ Wheelchair Accessible Vacation Homes in or Near Siesta Key
Property Image From $407
         

10.0 (22 Reviews)
Condo
  • Air Conditioner
  • Parking
  • Pool
Property Image From $361
         

10.0 (1 Review)
Apartment
  • Air Conditioner
  • Parking
  • Pool
Property Image From $392
         

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10.0 (6 Reviews)
Apartment
  • Air Conditioner
  • Parking
  • Pool
Property Image From $236
         

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9.1 (1619 Reviews)
Resort
  • Air Conditioner
  • Parking
  • Pool
Property Image From $399
         

10.0 (117 Reviews)
Condo
  • Air Conditioner
  • Parking
  • Pool

Siesta Key Varoom and Airbnb Places to Stay Under $200

Over 549+ Siesta Key Varoom and Airbnb Places to Stay Under $200
Property Image From $173
         

Property Image From $185
         

Property Image From $195
         

10.0 (44 Reviews)
House
  • 1100 ft² House
  • Air Conditioner
  • Parking
  • Pool
Property Image From $187
         

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9.0 (1141 Reviews)
Condo
  • Air Conditioner
  • Parking
  • Pool
Property Image From $197
         

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9.8 (22 Reviews)
House
  • Air Conditioner
  • Parking
  • View
Property Image From $197
         

9.8 (91 Reviews)
Condo
  • Air Conditioner
  • Parking
  • Pool
Property Image From $169
         

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9.5 (4 Reviews)
Apartment
  • Parking
  • Pool
  • Accessibility

Instantly Bookable Vacation Homes in Siesta Key

Over 3624+ Instantly Bookable Vacation Homes in or Near Siesta Key
Property Image From $403
         

10.0 (104 Reviews)
Condo
  • Air Conditioner
  • Parking
  • Pool
Property Image From $445
         

Property Image From $379
         

9.8 (162 Reviews)
Condo
  • Air Conditioner
  • Parking
  • Pool

About Siesta Key Vacation Rentals

With more than 6055 Siesta Key vacation rentals, we can help you find a place to stay. These rentals, including vacation rentals, Luxurycruises 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 Luxurycruises 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 1020.8 ft² on average, with prices averaging $503 a night.

Luxurycruises 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 1842
Holiday Apartments 571
Villas 419
Cottages 61
Hotels with Suites 29
Ski Chalet Rentals 16
Resorts 12
Others 1

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

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