Villa holiday rentals in Siesta Key

5 out of 5 average rating, 36 reviews

Siesta Villa

NEW to Airbnb - 1,478 SF Villa, in 25 acre, tropical, park-like setting, less than 5 miles from Siesta Key Beach. 7-night min. *AC in the lanai, enclosed with hurricane sliding doors and daybed provides a comfortable place to relax or take a nap. LED string lights provide a romantic ambiance. * HIGH SPEED INTERNET (200 mbps) *Enjoy the beautiful pool and spa *Modern Kitch w Quartz tops *Master BR suite & 2nd BR separated by two baths *Bikes, beach chairs, towels, coolers, racket sport equip.

4.92 out of 5 average rating, 158 reviews

Villa in Nokomis

May SALE 189/nt Sarasota! New Reno Villa 2BR/2BTH

EXCLUSVE CASEY KEY beach just .5 mi. away!! Sarasota 10 mins away! Miles of uncrowded beach! Two KING bedrooms, two bath villa! The Villa is a short 1 minute drive from Casey Key Beach! Two new 55" 4K T.V's. New appliances and furnishings throughout! Kayaking, biking, boating... all right here! Lush tropical backyard and fire pit. There are many wonderful restaurants and shops within a five minute drive. Restoring this Villa has been a labor of love for us, read our reviews!! Come stay...:)

Top guest favourite

4.98 out of 5 average rating, 46 reviews

Village Des Pins - 2 bedroom 2 bath villa

Village des Pins is a community of tranquil villas with lush greenery, ponds, wildlife, oversized heated pool, hot tub, tennis courts, clubhouse w/ pool table, & outdoor grilling area. This resort-like villa is located minutes away from Siesta Key beach, Lido beach, Venice beach, MOTE Marine Laboratory & Aquarium, Ringling museum, garden and theater, Big Cat Habitat, golf courses, fine dining & shopping. Nearby: Publix, Costco, Target, Sprouts, Detwiler farm market, Starbucks, Chick-fil-A, Pizza

4.85 out of 5 average rating, 114 reviews

Updated Downtown Sarasota Villa, 2b/2b

Enjoy a stylish experience at this centrally-located 2 bedroom, 2 bathroom attached villa in historic Laurel Park, downtown Sarasota. New 75” smart TV! Sleeps 6. Bedroom 1: King bed w/ en suite bathroom. Bedroom 2: 2 queen beds. Granite kitchen. 2 bathrooms. Fenced outdoor paver patio w/washer & dryer. Updated 2022. Free parking outside villa. Walking distance to downtown Sarasota, Selby Gardens, Marina Jack, Main St & more. Pottery Barn furnishing, beachy vibe & free WiFi! Free parking too!

4.75 out of 5 average rating, 126 reviews

Aloha Villa Pet Friendly 3 miles to Siesta Key #2

Your home away from home! Relax with your family & friends in this single story duplex in a quiet neighborhood, located a few miles from Siesta Key and Lido. Featuring original terrazzo floors and 3 br, this home offers a perfect cool and comfortable getaway for your family and pet. - Sleeps 7 people - Central location: Siesta Key 3 miles away Lido Key 4 miles - Fenced in backyard - Soft luxury bath towels - Beach chairs, umbrella, rolling cooler, toys - Fully stocked kitchen with Instant Pot

4.89 out of 5 average rating, 202 reviews

Villa in Lido Key

Entire Standalone Villa,1.2k sf,1 block Lido Beach

Welcome to our cute, spacious, sun filled and newly renovated Beach Villa. A Happy place for sandy feet, friends, and family. The Villa is located 1 block away from world famous Lido Beach, a 7 min walk to St Armand's Circle, and a short 3 mile drive to grocery shopping & the excitement of downtown Sarasota. The 2 bdr villa comfortably sleeps up to 6 people and features a private outdoor patio, spacious dining area, in-unit washer/dryer & dedicated parking. Come enjoy a taste of paradise!

4.82 out of 5 average rating, 68 reviews

Villa in Siesta Key

Paradise Villa on Siesta Key

Beachy villa on Siesta Key that makes you feel like you're REALLY on vacation! Located on ground level so no stairs to carry beach gear up. Walking distance to two beautiful white sand Siesta Key beach access points. Screened in private lanai/porch to relax, read or eat in while still being outdoors. Walking distance to many great restaurants, stores & marina/activities. Heated pool is great after a day at the beach. Covered carport parking. Free shuttle stop close by to explore Siesta Key.

5 out of 5 average rating, 27 reviews

Courtyard Villa w/Pool, Spa & Sauna close to Beach

Gorgeous courtyard pool home feathers high end quality construction throughout with high end upgrades, open split floor plan, high 10' volume cielings, porcelain and luxury plank floors, elegant designer chic touches make this home ideal for entertaining. Modern, open kitchen w/stainless steel appliances, Calcutta quartz countertops, large center island. Courtyard features outdoor kitchen, Jacuzzi, Sauna & outdoor shower. Walking distance to downtown restaurants and very close to beaches.

5 out of 5 average rating, 4 reviews

Newly Remodeled Luxury Beach Villa on Siesta Key!

The newly remodeled 2 bed / 2 bath Villa sleeps up to 6 people. The Master bedroom features a king-size bed with an attached bathroom and HD TV and entertainment system. The Guest Bedroom features one twin size bed, a bunk bed with a full-size bottom bed, and a HD TV. The comfortable living room is furnished with plenty of seating, a HD flat screen with 5.1 Dolby surround sound system and bar area. The gourmet kitchen is loaded with anything you'll need for cooking and entertaining!

4.87 out of 5 average rating, 30 reviews

3690 White Pine

Short distance to Siesta Key beaches, golf courses, shopping, restaurants and downtown. Resort style Community with large heated pool, hot tub, 2 tennis courts (one with lights), club house with pool table and space to rent for parties, grills, lakes and much more. 2 bedroom, 2 bath villa, 1 car garage and screened-in lanai, split floor plan, high ceilings, very light and bright. 3 TVs, Wifi Internet service provided. Guest Bdrm with 1 queen and 1 twin size beds.

5 out of 5 average rating, 14 reviews

Villa in Siesta Key

Modern, Walkable, Updated, Private.

WALK/BIKE/TROLLEY to Siesta Beach and Village. Relax and unwind in our spacious, sun-filled villa that is situated in an idyllic private neighborhood. Enjoy quiet surroundings, perfectly situated within steps to all that Siesta Key has to offer. The community pool is heated and located in the center of the neighborhood just steps away from the villa. The entrance to the private pier is on our lane ready to show off the amazing Siesta Key skies at sunset.