Siesta Key holiday rentals

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Recommended by KAYAK

Best Siesta Key holiday rentals

Most recommended holiday rentals in Siesta Key

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Siesta Key Beachside Villas - Siesta Key - Patio
Free Wi-Fi
Pool
Pet-friendly
Air conditioning
Siesta Heron Suites & Villas - Siesta Key - Living room
Free Wi-Fi
Pool
Air conditioning
Siesta Key Island Rentals - Siesta Key - Pool
Siesta Key Island Rentals
Siesta Key, FL, United States
8.5Very Good(49)
Parking
Pool
Air conditioning
Siesta Key Village-Suite #4: A block to the Beach! - Siesta Key - Beach
Parking
Free Wi-Fi
Pet-friendly
Air conditioning
One Ocean - B 1103 - Siesta Key - Beach
One Ocean - B 1103
Siesta Key, FL, United States
9.0Wonderful(23)
Free Wi-Fi
Air conditioning
Bianco Sands by Beachside Management - Siesta Key - Patio
Parking
Free Wi-Fi
Air conditioning
Siesta Sands Beach Resort Gulf View - Siesta Key - Outdoor view
Parking
Free Wi-Fi
Air conditioning
Siesta Sands Beach Resort 4th Floor with Elevator - Siesta Key - Beach
Parking
Free Wi-Fi
Air conditioning
Steps to #1 Beach in America Siesta Beach! - Siesta Key - Patio
Parking
Free Wi-Fi
Air conditioning
Beachfront Getaway in Siesta Key - Siesta Key - Beach
Free Wi-Fi
Pool
Air conditioning
#1us Siesta Key Beach Pool House - Siesta Key - Living room
Parking
Free Wi-Fi
Pool
Air conditioning
Beachpoint Cottages - Siesta Key
Beachpoint Cottages
Siesta Key, FL, United States
9.0Wonderful(486)
Parking
Free Wi-Fi
Pet-friendly
Air conditioning
Siesta Key Beach - Bari 665 #2 - Siesta Key
Free Wi-Fi
Air conditioning
The Inn at Turtle Beach (Adults Only) - Siesta Key
Free Wi-Fi
Air conditioning
One Ocean - A 1101 - Siesta Key
One Ocean - A 1101
Siesta Key, FL, United States
9.1Wonderful(16)
Air conditioning
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KAYAK’s insights for holiday 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 November, with average rates of £150. In comparison, February is the most expensive month, with prices at £241.

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

Saturday offers the lowest rates in Siesta Key, with an average nightly price of £159. The highest prices are found on Thursday, with average rates at £209.

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

Book at least 88 days before your stay begins to get the best price for your Siesta Key vacation rental.

Good to know

Low season

High season

Average price (weeknight)

June
March
£413
Cheapest month to stay with an average 33% drop in price.
Most expensive month to stay with an average 81% rise in price.
Average Sun - Thu price over the last 2 weeks.

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

  • Siesta Beach is the largest beach in Siesta Key Island. It is located about 1.3 miles from Hampton Inn Sarasota Ridge and Dream Vacation Home, Siesta Key holiday rentals located in the heart of the Village. Another major beach located on the southwest side of Siesta Key Village is Turtle Public Beach.
  • The most popular out of the pubs and clubs in Siesta Key is the Beach Club. In addition, pubs and restaurants near Comfort Suites Sarasota are open daily from noon till 02:00. Enjoy hanging out at the Oasis Beach Villa while playing pool games or drinking your favourite beer at the nearby Hyatt Place Sarasota pub.
  • Going shopping is the best way to find a unique souvenir and know the locals in Siesta Key. Make a stop at Siesta Key Outfitters, the village’s largest store, dealing with all kinds of souvenirs you ever desired. Skate Shop and CaliFlorida Surf stores are conveniently located opposite SpringHill Suites by Marriott, one of the Siesta Key holiday rentals ideal for families and lovers.
  • Siesta Key is known for its wide, sandy beachside amenities. Crescent Beach is the island’s largest and most decorated beach. It is located just a few minutes’ walk from getaway homes, such as Ramada by Wyndham and Best Western Plus Gateway.
  • If you’re looking for a perfect place to truly enjoy your honeymoon, Beach Club Siesta Key, Daiquiri Deck, and Blasé Café have you covered. While these getaway facilities can sometimes be crowded, there are still plenty of calm places to enjoy your intimate time. La Quinta Inn & Suites got a range of rental options to suit any group size, including families and solo travellers.
  • Beachfront, pool, air-conditioned, airport shuttle, and pet friendly are the most popular holiday rental property amenities in Siesta Key
  • Holiday rentals in Siesta Key are around 63% more expensive than hotels on average. Search here to compare prices for all accommodation types in Siesta Key.
  • The best holiday rental properties in Siesta Key are Siesta Key Beach - Tropea 665 #3 (9.7, 32 reviews), Siesta Sands Beach Resort Gulf View (9.7, 48), and Villa Vista Mare - 675 (9.6, 21), based on ratings and reviews from real travellers.
  • If you’re looking for a cheap holiday rental in Siesta Key, you should consider visiting during the low season. The cheapest holiday homes in Siesta Key can be found in June and February.
  • The cheapest night for renting a holiday home in Siesta Key is Tuesday. In contrast, the most expensive is Monday.
  • Holiday rentals are a popular choice for both long and short-term stays. KAYAK users usually book their holiday rental in Siesta Key for 5 days.

FAQs when booking a holiday home in Siesta Key

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

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

  • What are some of the most-loved holiday rentals available in Siesta Key?

    If you’re looking for something special, the holiday rental most loved by KAYAK users is Bianco Sands by Beachside Management.

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

    There are a number of dog and pet-friendly Siesta Key holiday rentals, with around 10% allowing you to bring your pet along with you.

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

    In the last 72 hours, users have found Siesta Key holiday rentals for tonight for as low as £230. Search here for similar prices

  • How much is a holiday rental in Siesta Key for this weekend?

    In the last 72 hours, users have found Siesta Key holiday rentals for this weekend for as low as £230 per night. Search here for similar prices

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

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

  • What are the benefits of self-catering in Siesta Key Holiday Rentals?

    Siesta Key is a lively and ever-busy city with many boutique stores and large food stores, where visitors can order their favourite and hard-to-find delicacies. For a true experience with Siesta Key local foods, visit one of the city’s food markets, including Crescent Beach Grocery and Morton’s Siesta Market.

  • Where are the best Siesta Key holiday homes with a great view located?

    For a great city and sea view in Siesta Key, consider Siesta Key house rentals close to the public beach. The facility offers one of the best rainbow views every evening. For the best sunset viewing in Siesta, consider Siesta Key holiday rentals next to or opposite Sunset Point. Then, enjoy different viewpoints by taking a walk along Siesta Public Beach.

  • Which are the top family destinations in Siesta Key?

    Siesta Key Beach is arguably one of the best travel destinations for families. It offers safe, shallow, calm water for swimmers of all ages. All amenities, including lifeguards, are readily available. Siesta Key Beach is located within walking distance from Tropical Breeze Resort. Family activities to engage in during your stay include kayaking, fish offshore or inshore, swimming, relaxing on the bench, and playing mini-golf.

  • Where are the good nightlife holiday rentals in Siesta Key?

    The admiration for Siesta Key isn’t just due to its glorious beaches. You can do so many other things during your Siesta Key visit, including a fun nightlife scene in major restaurants and popular bars. The Cottage, 3.14 Craft Beer and Spirits, and Gilligan’s Island Bar & Grill are some of the places to spend your night with a friend or partner.

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 holiday rental.

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

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