Vacation rentals in Siesta Beach

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Top-rated vacation rentals in Siesta Beach

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Guest favorite

Apartment in Siesta Key

4.99 out of 5 average rating, 139 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

Sep 11 – 18

G$94,666 GYD per night

Guest favorite

Guest suite in Sarasota

4.94 out of 5 average rating, 477 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!

Dec 19 – 26

G$29,420 GYD per night

Guest favorite

Guesthouse in Sarasota

4.93 out of 5 average rating, 454 reviews

La Casetta: "the little house" near to the beaches

La Casetta means, in Italian, a tiny house. Set in a private, peaceful, mature Florida tropical garden, a real hideaway. I am proud of the cleanliness of our property, however in this new reality that we live in, we do carry out enhanced cleaning and sanitizing between guests. We also practice social distancing, insofar as guests have their own part of our luscious back garden as well as your own entrance. La Casetta has 1 queen sized bed, bathroom & kitchenette. Wifi & Netflix available.

Aug 12 – 19

G$19,328 GYD per night

Guest favorite

Guest suite in Sarasota

4.98 out of 5 average rating, 103 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!

Aug 31 – Sep 7

G$24,785 GYD per night

Guest favorite

Condo in Siesta Key

4.96 out of 5 average rating, 273 reviews

On the Beach; Siesta Key SunBum Studio

STEPS TO YOUR OWN PRIVATE BEACH!! NO TRICKS or GIMMICKS LIKE OTHER LISTINGS on the KEY. This is the only studio in the Palm Bay Club tower on ground level with breathtaking views of the white sand and gulf waters. The Palm Bay Club offers 2 pools, hot tub, new gym, boat docks, fishing pier, outdoor grills, tennis/pickle ball courts; not to mention FREE parking+ beach lounge chairs. Enjoy 2 free bikes day rental with booking! You are sure to enjoy your time here on the #1 U.S. Beach.

Mar 26 – Apr 2

G$95,615 GYD per night

Guest favorite

Apartment 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!

Sep 30 – Oct 7

G$29,713 GYD per night

Guest favorite

Guest suite in Sarasota

4.94 out of 5 average rating, 113 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.

Oct 6 – 13

G$22,523 GYD per night

Guest favorite

Home in Sarasota

4.98 out of 5 average rating, 198 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 .

Sep 7 – 14

G$21,532 GYD per night

Guest favorite

Guest suite in Sarasota

4.91 out of 5 average rating, 269 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 :-)

Nov 19 – 26

G$20,510 GYD per night

Guest favorite

Guest suite in Sarasota

4.97 out of 5 average rating, 350 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

Sep 2 – 9

G$19,176 GYD per night

Guest favorite

Guesthouse in Sarasota

4.86 out of 5 average rating, 368 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

Oct 21 – 28

G$23,853 GYD per night

Guest favorite

Condo in Siesta Key

4.93 out of 5 average rating, 180 reviews

Siesta key getaway!

perfect and very comfortable 4th floor condo with elevator, screened in lanai, fully stocked kitchen and full bath. laundry facilities on the premises, a tennis court. We supply beach chairs, umbrellas, a rolling cooler and big beach bag. There is a beautiful dock on the intercoastal side of us with picnic chairs, grills, and you may even see dolphins playing !

Jun 23 – 30

G$32,181 GYD per night