Pirate Cove Cottages - Vacation Rentals in Siesta Key

Across The Street From #1 Beach From US $286
         

10.0 (321 Reviews)
Cottage
  • Air Conditioner
  • Parking
  • Pet Friendly
Coriander Cottage From US $299
         

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9.3 (3 Reviews)
House
  • Air Conditioner
  • Parking
  • Pet Friendly
The Inn On Siesta Key From US $295
         

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10.0 (190 Reviews)
Cottage
  • Air Conditioner
  • Parking
  • Pet Friendly
Cabana Cottage Across street from Beach and Heated Pool From US $968
         

10.0 (5 Reviews)
Cottage
  • Air Conditioner
  • Parking
  • Pet Friendly
Nook Cottage Across street from beach and Heated Pool From US $499
         

10.0 (4 Reviews)
Cottage
  • Air Conditioner
  • Pet Friendly
  • Pool
Nest Cottage Across street from beach and Heated Pool From US $766
         

Luxury Places to Stay in Siesta Key

Over 5670+ 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
Entire Resort on Heron Lagoon, the Siesta Key Bungalows From US $5,239
         

10.0 (1 Review)
House
  • Air Conditioner
  • Parking
  • Pet Friendly
Siesta Key Oceanfront Palace with Private Beach From US $5,226
         

9.6 (18 Reviews)
House
  • Air Conditioner
  • Parking
  • Pet Friendly

Top-Rated Vacation Rentals with a Pool in Siesta Key

Over 4533+ Top-Rated Vacation Rentals with a Pool in or Near Siesta Key
A Bayside Treasure - Outstanding Waterfront Views! From US $255
         

10.0 (208 Reviews)
Condo
  • Air Conditioner
  • Parking
  • Pool
Full Gulf Views Across from Siesta Key Beach From US $317
         

10.0 (179 Reviews)
Condo
  • Air Conditioner
  • Parking
  • Pool
🦩Book Me Baby! Bayview Beauty at Siesta Key 🦩 From US $337
         

10.0 (170 Reviews)
Condo
  • Air Conditioner
  • Parking
  • Pool

Pet-Friendly Vacation Rentals in Siesta Key

Over 965+ Pet-Friendly Vacation Rentals in or Near Siesta Key
323 Canal Rd - Siesta Key Village Condo From US $302
         

Large Vacation Homes & Villas in Siesta Key

Over 927+ Large Vacation Homes & Villas in or Near Siesta Key
Siesta Key Retreat Sarasota Florida From US $1,574
         

10.0 (41 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
Island House Beach Resort V36 From US $490
         

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9.0 (16 Reviews)
Villa
  • Air Conditioner
  • Pool
  • TV
Island House Beach Resort V11 From US $458
         

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

Wheelchair Accessible Vacation Homes in Siesta Key

Over 1787+ 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
Siesta Key From US $392
         

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10.0 (6 Reviews)
Apartment
  • Air Conditioner
  • Parking
  • Pool
Little slice of paradise, Siesta Dunes 2-209. From US $430
         

10.0 (22 Reviews)
Condo
  • Air Conditioner
  • Parking
  • Pool
Exceptional Beachfront condo on Crescent Beach From US $373
         

10.0 (118 Reviews)
Condo
  • Air Conditioner
  • Parking
  • Pool
Siesta Key For Me @ The Palm Bay Club From US $454
         

10.0 (107 Reviews)
Condo
  • Air Conditioner
  • Parking
  • Pool

Siesta Key Varoom and Airbnb Places to Stay Under $200

Over 454+ Siesta Key Varoom and Airbnb Places to Stay Under $200
Barb's 3 Wishes.Sun, Sand, Siesta From US $187
         

9.8 (92 Reviews)
Condo
  • Air Conditioner
  • Parking
  • Pool
Siesta Bayside Closest to the Beach From US $185
         

Captiva Beach Resort From US $152
         

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9.0 (1169 Reviews)
Condo
  • Air Conditioner
  • Parking
  • Pool
Chloe's Villa on Siesta Key, A Private 1/1 Escape From US $184
         

10.0 (27 Reviews)
House
  • Air Conditioner
  • Parking
  • Pool
Ideal location Siesta Key From US $179
         

10.0 (5 Reviews)
Condo
  • Air Conditioner
  • Parking
  • Pet Friendly

Instantly Bookable Vacation Homes in Siesta Key

Over 3690+ Instantly Bookable Vacation Homes in or Near Siesta Key
Amazing Condo! Restored from Hurricane! From US $333
         

9.8 (162 Reviews)
Condo
  • Air Conditioner
  • Parking
  • Pool
Relaxing Siesta Key Condo From US $233
         

9.8 (39 Reviews)
Condo
  • Air Conditioner
  • Parking
  • Pool

About Siesta Key Vacation Rentals

With more than 86 Siesta Key vacation rentals, we can help you find a place to stay. These rentals, including vacation rentals, Piratecovecottages 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 Piratecovecottages 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 764.14 ft² on average, with prices averaging $524 a night.

Piratecovecottages 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
Cottages 58
Vacation Homes 23
Holiday Apartments 4
Hotels with Suites 1

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

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