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Siesta Key vacation rentals

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Best Siesta Key vacation rentals

Most recommended vacation rentals in Siesta Key

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Siesta Key Beachside Villas - Siesta Key - Patio
Siesta Key Beachside Villas
Siesta Key, FL, United States
8.5Very good(888)
Free Wi-Fi
Pool
Pet friendly
C$ 541+
Check availability
Siesta Heron Suites & Villas - Siesta Key - Living room
Siesta Heron Suites & Villas
Siesta Key, FL, United States
8.4Very good(306)
Free Wi-Fi
Pool
C$ 403+
Check availability
Siesta Key Island Rentals - Siesta Key - Pool
Siesta Key Island Rentals
Siesta Key, FL, United States
8.6Very good(46)
Parking
Pool
C$ 573+
Check availability
Siesta Key Village-Suite #4: A block to the Beach! - Siesta Key - Beach
Siesta Key Village-Suite #4: A block to the Beach!
Siesta Key, FL, United States
9.1Wonderful(22)
Parking
Free Wi-Fi
Pet friendly
C$ 398+
Check availability
One Ocean - B 1103 - Siesta Key - Beach
One Ocean - B 1103
Siesta Key, FL, United States
9.0Wonderful(23)
Free Wi-Fi
C$ 369+
Check availability
Siesta Sands Beach Resort Gulf View - Siesta Key - Outdoors view
Siesta Sands Beach Resort Gulf View
Siesta Key, FL, United States
9.7Wonderful(47)
Parking
Free Wi-Fi
C$ 859+
Check availability
Gulf Holiday - Siesta Key - Living room
Gulf Holiday
Siesta Key, FL, United States
8.1Very good(87)
Parking
Free Wi-Fi
C$ 505+
Check availability
Beachpoint Cottages - Siesta Key
Beachpoint Cottages
Siesta Key, FL, United States
8.9Very good(478)
Parking
Free Wi-Fi
Pet friendly
C$ 562+
Check availability
The Inn at Turtle Beach (Adults Only) - Siesta Key
The Inn at Turtle Beach (Adults Only)
Siesta Key, FL, United States
8.3Very good(198)
Free Wi-Fi
C$ 419+
Check availability
Siesta Key Beach - Bari 665 #2 - Siesta Key
Siesta Key Beach - Bari 665 #2
Siesta Key, FL, United States
8.9Very good(22)
Free Wi-Fi
C$ 368+
Check availability
Walk To Beach, Updated Condo, Private Pa - Siesta Key
Walk To Beach, Updated Condo, Private Pa
Siesta Key, FL, United States
9.3Wonderful(38)
C$ 700+
Check availability
One Ocean - A 1101 - Siesta Key
One Ocean - A 1101
Siesta Key, FL, United States
8.7Very good(16)
C$ 389+
Check availability
Siesta Beach Cottage, Sleeps 6, Walk To - Siesta Key
Siesta Beach Cottage, Sleeps 6, Walk To
Siesta Key, FL, United States
7.0Good(23)
C$ 584+
Check availability
Siesta Key Beach - Capri 665 #4 - Siesta Key
Siesta Key Beach - Capri 665 #4
Siesta Key, FL, United States
7.6Good(22)
Free Wi-Fi
C$ 423+
Check availability
Sarasota Pool Apartment - Siesta Key
Sarasota Pool Apartment
Siesta Key, FL, United States
Pool
C$ 1,812+
Check availability
Ideal Beach Cottage Steps To Siesta Beac - Siesta Key
Ideal Beach Cottage Steps To Siesta Beac
Siesta Key, FL, United States
5.8Fair(15)
C$ 551+
Check availability
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C$ 282 - C$ 1,939C$ 1,939 - C$ 3,596C$ 3,596 - C$ 5,253C$ 5,253 - C$ 6,908C$ 6,908+ per night

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KAYAK’s insights for vacation rentals in Siesta Key

Discover seasonal trends, ideal booking windows, and other data-driven tips to plan your stay in Siesta Key with confidence.

Which month has the cheapest vacation rental rates in Siesta Key?

Vacation rentals are cheapest in Siesta Key in December, with average rates of C$ 499. In comparison, March is the most expensive month, with prices at C$ 1,158.

What is the cheapest day of the week to book a vacation rental in Siesta Key?

Tuesday offers the lowest rates in Siesta Key, with an average nightly price of C$ 553. The highest prices are found on Monday, with average rates at C$ 729.

How early should you book a vacation rental in Siesta Key?

Book at least 14 days before your stay begins to get the best price for your Siesta Key vacation rental.
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Good to know

Low season

April

High season

February

Average price (weeknight)

C$ 671

Average price (weekend night)

C$ 440
Cheapest month to stay with an average 59% drop in price.
Most expensive month to stay with an average 126% rise in price.
Average Sun - Thu price over the last 2 weeks.
Average Fri & Sat price over the last 2 weeks.

KAYAK's top tips for finding Siesta Key holiday rental deals

  • For those visiting Siesta Key with their kids or family, consider staying at Sea Spray. This family-friendly vacation rental is famous for its family rooms and a policy that allows kids to stay for free. Additionally, your kids will be kept busy with the children’s television networks. The establishment also has a bicycle rental center where you can rent a bike to help you spend some quality time outdoors.
  • If you are looking for Siesta Key vacation rentals ideal for a romantic getaway, consider staying at Siesta Heron Suites & Villa. This Siesta Key rental house gets everything right with its satisfying combination of amenities for you to create incredible romantic memories on the beach. And if you’re on your honeymoon, you will get lots of amenities and cozy accommodations for you and your better half.
  • If you are looking for Siesta Key vacation rentals near the airport, consider staying at The Ringling Beach House. This vacation rental is only a 9min drive away from Sarasota International Airport (SRQ). This, however, tends to vary during the morning and evening rush hours.
  • For those who love swimming and would love to stay at a Siesta Key vacation rental with a pool, consider staying at Midnight Cove # 714. This beachfront accommodation has a modern outdoor pool with cozy furnishings, and you will have certified lifeguards ensuring your safety whenever you’re in the pool.
  • If you are looking for a quiet stay, a place where you can unwind and relax after a busy week, consider staying at The Zen Den. This establishment has a serene environment, convenient for those who would love their privacy.
  • Beachfront, pool, air-conditioned, airport shuttle, and pet friendly are the most popular vacation rental property amenities in Siesta Key
  • Vacation rentals in Siesta Key are around 27% more expensive than hotels on average. Search here to compare prices for all accommodation types in Siesta Key.
  • The best vacation rental properties in Siesta Key are Endless Views - 532 (9.9, 25 reviews), Siesta Sands Beach Resort Gulf View (9.7, 47), and Clean Perfectly Remodeled Townhome, Steps From the Private Beach. 3 night min (9.7, 62), based on ratings and reviews from real travelers.
  • If you’re looking for a cheap vacation rental in Siesta Key, you should consider visiting during the low season. The cheapest vacation homes in Siesta Key can be found in April and July.
  • The cheapest night for renting a vacation home in Siesta Key is Sunday. In contrast, the most expensive is Monday.
  • Vacation rentals are a popular choice for both long and short-term stays. KAYAK users usually book their vacation rental in Siesta Key for 7 days.
  • The cheapest Siesta Key vacation rental found on KAYAK in the last 2 weeks was C$ 273, while the most expensive was C$ 273.
See more tips

FAQs when booking a vacation home in Siesta Key

  • What types of vacation rentals are available in Siesta Key?

    There are loads of different property types that you can make your vacation home in Siesta Key. You’ll find apartments, bungalows, chalets, condos, cottages, houses, homestays and villas.

  • Are there any pet-friendly vacation rentals in Siesta Key?

    There are a number of dog and pet-friendly Siesta Key vacation rentals, with around 9% allowing you to bring your pet along with you.

  • How much is a vacation rental in Siesta Key for tonight?

    In the last 72 hours, users have found Siesta Key vacation rentals for tonight for as low as C$ 450. Search here for similar prices

  • How can I find vacation rentals near me in Siesta Key?

    Take a look at our vacation rentals map to find the best vacation rental homes near you.

  • Which Siesta Key vacation rentals are pet-friendly?

    Most Siesta Key house rentals are pet-friendly. For those who would love to have their furry friend with them during their stay in Siesta Key, consider staying at Beachpoint Cottages. This establishment welcomes your pup with a freshwater bowl and a doggy menu. Additionally, your well-behaved friend will have a special spot reserved in the shade for watching squirrels and birds. What’s more, they charge a reasonable fee for pet stays.

  • Which vacation rentals in Siesta Key offer a fitness center?

    For those who would love to keep up with their fitness routine during their vacation in Siesta Key, consider staying at Siesta Key Beachside Villas. This vacation rental has a modern fitness center with a fully equipped gym with fitness equipment like weights, treadmills, and resistance bands. Once you book a fitness session, you will be assigned a personal trainer who can handle beginners and pros.

  • Which vacation rentals in Siesta Key are near famous attraction sites?

    If you are visiting Siesta Key to experience its great attraction sites, consider staying at The Destin Complex, Beach Club. This highly celebrated vacation rental gives you breathtaking views of the Gulf of Mexico waters, while Siesta Key’s famous Crescent Beach is just steps away. Other major attractions around it include Point of Rocks, Silver City Sarasota, and Sunshine & Sand Hidden Treasures.

  • Which vacation rentals in Siesta Key have offer free parking?

    For those who would love to book a vacation rental with free parking, consider staying at Happy Clam. This cozy establishment offers free parking for its guests, with the cars under 24-hour surveillance.

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Where to stay in Siesta Key?

Our map will help you find the perfect place to stay in Siesta Key by showing you the exact location of each vacation rental.

Everything you need to know for your stay in Siesta Key

Siesta Key vacation rental deals. Search for vacation homes, apartments, condos, cabins, cottages, villas and more in Siesta Key. Find cheap vacation homes to rent in Siesta Key. KAYAK searches hundreds of travel sites to help you find and book a vacation rental in Siesta Key that suits you best.

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