Holiday rentals in Siesta Key

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Top-rated holiday rentals in Siesta Key

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Guest favourite

Guest suite in Sarasota

4.94 out of 5 average rating, 479 reviews

Studio Apartment. Priv Yard. 5 min to Siesta Key!

Self checkin. Includes kayak and bikes! You’ll love my place because of the coziness, the high ceilings, and the location. My place is good for couples, solo adventurers, and business travelers. Converted garage space. Your own private fenced back yard, kitchenette, fridge, private bathroom, Amazon Firestick with Netflix, Hulu and dock/boat ramp just 30 sec from your door and in a beautiful neighborhood. Just a 10 min bike ride to Siesta Key. The #1 beach in America! What more could you ask for!

9–16 Aug

$146 SGD per night

Guest favourite

Serviced apartment in Siesta Key

4.99 out of 5 average rating, 142 reviews

Siesta Key #1 Beach, pickle ball & tennis paradise

Beautiful Apartment w/ Hotel Services, at Siesta Key Beach. Totally remodeled. Fully equipped to spend the best holidays with family or friends. Condo hotel, on the best beach in Siesta. Beach pool, shade pool (heated), gym, 3 tennis courts on site (2 clay, 1 hard) and 2 pickle ball courts. Master bedroom with King bed. The Mattress is a SAATVA ORGANIC. 2nd room with 2 single beds, and a queen sofa bed, in the living room. Pack n Play 600 MB Wifi. HD TV. 70” Smart TV Nesspreso, Keurig Machines

14–21 Dec

$613 SGD per night

Guest favourite

Guest suite in Sarasota

4.98 out of 5 average rating, 106 reviews

Mid-Century Modern Beach Getaway

Heart of Southside Village 10 minutes from #1 beach in the USA, Siesta Key. Five-minute drive to downtown Sarasota, 10 minutes to St. Armand Circle, Lido & Longboat Key. Enjoy this peaceful space within walking distance to shopping, restaurants & groceries. Charming private guest house offers a queen bed, sitting chairs, table, dresser, large ensuite bathroom with a walk-in shower & private outdoor sunny space and patio. Use the grill to cook your next meal. It's the perfect couple's getaway!

26 Aug – 2 Sep

$149 SGD per night

Guest favourite

Flat in Sarasota

5.0 out of 5 average rating, 117 reviews

New Apartment In a Private House Near Siesta

Large brand new construction 900 square foot 1 bedroom apartment. Beautifully furnished, efficient apartment attached to the side of the main house. This unit has a private entrance with bright, modern interior. The apartment offers 2 queen size beds. The full bathroom has a large shower. A Washer and dryer located inside the apartment. Nestled on a quiet street with easy access to Siesta key. Located 1 mile from the Stickney Point bridge with easy access to Siesta Key. Great location!

17–24 Sep

$188 SGD per night

Guest favourite

Guest suite in Sarasota

4.93 out of 5 average rating, 115 reviews

Sweet Siesta Suite

Sweet spot with the best of both Sarasota and Siesta Key - your private oasis for relaxing and rejuvenating. Whether you choose to chill or find adventure it is all within reach! Siesta Key beaches, Village with shops, restaurants, and bars; Sarasota culture, arts, and entertainment; quaint Gulf Gate shops and eateries ...the possibilities truly are endless. Regardless of how you choose to spend your time here, you will be sure to create lasting memories to share and leave wanting more.

14–21 Sep

$150 SGD per night

Guest favourite

Home in Sarasota

4.99 out of 5 average rating, 202 reviews

The Key Lime Cottage 2 miles from Siesta Key Beach

Great location. 2 miles from the # 1 rated Beach in America , Siesta Key . The cottage is near several other beaches as well. Close to restaurants and shopping. 1 hour from Tampa and 2 hours from Orlando. The Key Lime Cottage is totally updated with new stainless steel & granite in the kitchen . There are two new beds ..... one is a queen size and the other is a full size. (URL HIDDEN) Linens & towels are all new. New tile and wood floors throughout. Quite neighborhood for walking .

26 Apr – 3 May

$155 SGD per night

Guest favourite

Home in Sarasota

4.99 out of 5 average rating, 131 reviews

Adorable Bungalow Fire pit/outdoor shower 2/1 Cute

Charming and tranquil two bedroom home located in central Sarasota. This adorable bungalow is just 6 miles from world famous Siesta Key Beach. Located on a quiet street you are just minutes from great restaurants and shopping. The house is an adorable bungalow with a sweet cottage feel inside. The backyard is private with a fence all around. You can enjoy laying in the hammock and by night sit around the fire pit. There is an outdoor shower with cold and hot water to enjoy.

23–30 Aug

$155 SGD per night

Guest favourite

Guest suite in Sarasota

4.91 out of 5 average rating, 274 reviews

Siesta Keys stylish and affordable Airbnb.

Relax while you stay in a colorful and warm Siesta Key/Sarasota neighborhood home that is only minutes from the famous Siesta Key beach. Enjoy your private, safe, and comfortable suite while being in close reach to all that Florida has to offer. Your suite is spacious and accommodating, wether your an individual, couple, family, or group of friends we have the space and amenities for you to maximize both your comfort and fun time while here in Florida :-)

16–23 Nov

$133 SGD per night

Superhost

Cottage in Siesta Key

4.84 out of 5 average rating, 133 reviews

Adorable Cozy Silver Sands Cottage on Siesta Key!!

Adorable one bedroom "Old Florida Cottage" on the intracoastal bay side of Siesta Key. This is a stand alone cottage, ground floor, no elevators or flights of stairs to mess with. New Pool with a tiki hut, fishing dock, boat basin (up to 24'), beach access 4 min. walk across Midnight Pass Rd. to the #1 beach with the whitest, softest sand you'll ever see! Hi Def TV in LR , Wifi, TV in BR, stocked with everything but your clothes and toothbrush.

17–24 Aug

$189 SGD per night

Guest favourite

Guest suite in Sarasota

4.91 out of 5 average rating, 135 reviews

★PRIVATE★ZEN STUDIO ★1 BLOCK TO SIESTA DRIVE

Japanese inspired relaxing 1 room studio attached to a home. Enjoy your own private entry which includes a large enclosed outdoor patio with Zen Rock Garden. Mini Kitchen for light cooking. The plush queen bed is a guest favorite for comfort! Listing price reflects the size (Charming 210sqf) without sparing comfort, quality, or location. Minutes drive to picturesque downtown Sarasota, and a few minutes more to Siesta Key & Lido Beaches.

16–23 Sep

$133 SGD per night

Guest favourite

Guest suite in Sarasota

4.97 out of 5 average rating, 351 reviews

Adorable studio close to Siesta beach!

Come stay in this private studio with its own fenced in patio in the back! Has shared washer and dryer. New Queen bed ,pullout couch (twin). gas grill,toaster oven/airfryer, microwave , hot plate for cooking and full fridge plus ac unit. Rainfall showerhead and river stones on shower floor. beach chairs ,towels available. Off street parking in driveway. The famous, huge fresh market " Detweilers" is only 1.5 miles away

23–30 Sep

$124 SGD per night

Guest favourite

Guest house in Sarasota

4.86 out of 5 average rating, 371 reviews

The Cottage, very close to Siesta Beach!

The cottage was built in 1926 and is in a Historic Neighborhood. Our location is a 10 min car ride or 25 min bike ride to the #1 Rated Siesta Key Beach and a short stroll to popular eateries and shopping areas. The cottage is cozy and has all the essentials of home. Private entrance, backyard, kitchenette with a full fridge. Ideal for 2 people but can accommodate more. Dogs welcome

4–11 Sep

$154 SGD per night