Villa holiday rentals in Siesta Key

5 out of 5 average rating, 46 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.

4.93 out of 5 average rating, 73 reviews

Siesta Key*PRIVATE BEACH*Gulf Side*Heated Pool

Beautifully updated in 2025 conveniently located BEACH SIDE on Siesta Key/Crescent Beach. Short 2 minute walk to our PRIVATE beach w/loungers. No walking across Midnight Pass. NO HUGE CROWDS. 1 large bedroom, PLUS a queen pull out sofa. FABULOUS fully equipped kitchen w/quartz counters,2 new smart TV's,GORGEOUS bathroom w/8ft shower,screened lanai,outdoor shower&electric grill. Steps to heated community pool,laundry facilities & free trolly. Walk to Stickney Point Restaurants/Bars/Rentals/Marina

4.92 out of 5 average rating, 166 reviews

The exterior of the villa features a light-colored facade with inviting landscaping. Tropical plants and palm trees are positioned around the entrance, which is framed by large windows and a welcoming pathway made of stone pavers leading to the front door.

Villa in Nokomis

APRIL OPEN 1 min to beach, New, PETS OK!, 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...:)

4.87 out of 5 average rating, 135 reviews

A light-filled living area features soft, neutral-toned sofas arranged around a glass coffee table atop a textured area rug. Decorative elements, such as a floral arrangement and softly glowing lamps, complement the inviting atmosphere. A doorway leads to the kitchen, enhancing the open layout.

Villa in Laurel Park

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!

A comfortable living and dining area is showcased, featuring a glass dining table with white wooden chairs. A cozy sectional sofa is arranged around a coffee table, with a rug underfoot. Natural light filters through two windows, complemented by decorative artwork on the walls.

4.93 out of 5 average rating, 27 reviews

Robinhood Beach Villa near Siesta Key Beach!

Now Booking winter and spring getaways! Reserve your getaway dates for December through April now! 30% off stays of 28 night or more!! Updated bath & kitchen Enjoy 4k TV and a work station inside, or our BBQ propane grill & fire pit outside in the large backyard w/ privacy fence. Walkable to great restaurants like Walt's Fish Market & Trader Joe's (across the street) & other shopping stores. We are only a few miles from the #1 Beach in the USA, Siesta Key Beach! Dogs up to 50lbs welcome.

4.9 out of 5 average rating, 225 reviews

A spacious living area is highlighted by a large sectional sofa and a wooden coffee table. A TV sits atop a media console, while glass doors provide access to the outdoor patio, allowing natural light to fill the room.

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!

A charming villa exterior is depicted, featuring a bright façade with a red-tiled roof. Lush green landscaping surrounds the property, with palm trees and various shrubs casting soft shadows on the well-maintained grass.

5 out of 5 average rating, 24 reviews

Sunshine Get a Way! Pool, Beach & Fun!

Completely Remodeled! Sunlight floods through every window of this end unit. All tile floors, granite counters, new appliances and all new furnishings. Fully equipped with everything you need to enjoy a carefree stay. King size bed in the master bedroom. Full size and twin bed in the guest bedroom. Peek a boo view of golf course and privacy green space view from lanai. Minutes from Westfiled Sarasota Square Mall, golf, restaurants and Siesta Beach which was recently named #1 beach in the USA.

4.88 out of 5 average rating, 295 reviews

A single-story home is surrounded by greenery and palm trees, showcasing a light green exterior. A narrow pathway leads to the entrance, flanked by decorative planters. The white fence adds charm and defines the front yard, with large windows allowing natural light into the interiors.

Villa in Laurel Park

Duplex - just mins to Siesta Beach - Pet Friendly

This is a 2/1 in Sarasota's Historic Laurel Park that offers a great downtown and beach experience! Walk/bike to historic downtown with shops, restaurants, bars, boutiques, parks, and music/theater. Minutes from the best beaches in the U.S. Enjoy the lanai & fenced backyard for privacy . Grill & enjoy your favorite beverage while watching your favorite show on the lanai ! Enjoy taking your pet for a walk & check out the historic homes in the area! Short term rental number VR24-00222

5 out of 5 average rating, 122 reviews

A relaxing outdoor space features a lounge chair adorned with a striped towel and a wide-brimmed hat. A tray holds a refreshing drink beside the crystal-clear pool, surrounded by lush tropical foliage and a colorful float visible in the water.

Villa in Arlington Park

Luxury Villa with Pool, Game Room, Near Beach

Welcome to your tropical luxury escape! Spacious living flows to the heated pool, game room and sunny patio—perfect for family fun. • Bedrooms: 4 private suites, plush linens to ensure restful nights. • Location: Quiet neighborhood just minutes from the sandy beach, dining and shopping hotspots. • Heated pool & sun loungers • Arcade-style game room • Fast Wi-Fi & 5-star cleanliness • Pet friendly with fenced yard Have questions? We reply in under an hour—book your stay today! VR24-00060

A light-filled bedroom contains two twin beds covered in soft blue bedding adorned with coral patterns. A dresser is positioned between the beds, and large windows with blinds provide natural light. Light curtains complement the neutral wall color, contributing to a serene setting.

4.86 out of 5 average rating, 138 reviews

Cozy, pet-friendly Home 3 miles to Siesta Key #1

Relax with your family & friends in this pet-friendly single story home in a quiet neighborhood, located within minutes from Siesta Key! This 3-bedroom home comfortably sleeps up to 7 people with 6 beds available. Other amenities include: - Central location: Siesta Key 3 miles away, Lido Key 4 miles - No stairs - Fenced in backyard, water and pet food bowls - Soft luxury bath towels - Beach chairs, umbrella, cooler, toys - Instant Pot, French press, dishwasher

A comfortable living area features a gray, U-shaped sectional sofa accompanied by a center coffee table. Natural light brightens the space, highlighting the light-colored tile flooring. The open layout connects the living area to a kitchen visible in the background.

4.92 out of 5 average rating, 39 reviews

Fully renovated villa on Siesta Key

FEBRUARY 2026 NOW OPEN SPECIAL PRICE Siesta Key, voted best in the United States, our villa is just across the street from this piece of paradise. We are in walking distance to over 15 restaurants and shops. Our villa is on ground level in a quiet area, a little tropical oasis with everything you need near by, take a stroll down Peacock Lane to the intracoastal. There is also a free trolley that runs up and down the island. Check out jkcondo for more info

A wooden walkway leads from lush greenery to the beach, flanked by palm fronds. The clear blue sky meets the horizon, and the sandy beach stretches out with colorful umbrellas and sunbathers visible in the distance.

5 out of 5 average rating, 18 reviews

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.

Popular amenities for Siesta Key villa rentals

Kitchen

Wi-Fi

Pool

Free parking on premises

Air conditioning

Private villa rentals

Villa in Lido Key

5 out of 5 average rating, 3 reviews

Beach Villa in Sarasota

A bright and open living area features comfortable seating including a gray sofa and black armchairs. A large window allows natural light, while a ceiling fan enhances airflow. The kitchen area is visible in the background, with stainless steel appliances and a dining table for four.

4.76 out of 5 average rating, 38 reviews

Clean & Modern, Close to Beach, Shopping, Food!

4.89 out of 5 average rating, 28 reviews

A charming beach home is set among palm trees, with a landscaped garden featuring colorful plants. A gravel pathway leads to the entrance, and patio seating is visible in the background, inviting guests to enjoy the outdoor space.

Villa in Anna Maria

Northshore BeachHouse West Anna Maria Island

4.76 out of 5 average rating, 21 reviews

The front entrance of a light blue house is framed by a manicured lawn and lush greenery. A clear pathway leads to the door, bordered by decorative stones and various potted plants. Tall trees provide shade and an inviting atmosphere.

Villa in Bayou Oaks

Tiki Bella Villa (Entire home with Pool)

A large, inviting pool is surrounded by lush greenery and tall pine trees. Several lounge chairs are visible around the pool area, with bright sunlight reflecting off the clear water. The depth marker indicates a shallow end of 3 feet 6 inches.

4.97 out of 5 average rating, 38 reviews

Vacation Villa/Resort Pool 4 miles to Siesta Key

The outdoor pool area features a spacious swimming pool alongside a hot tub. Surrounded by tall trees, the space offers a relaxing atmosphere with lounge chairs and umbrellas positioned around the pool deck. Clear blue skies enhance the inviting setting.

4.75 out of 5 average rating, 12 reviews

Charming 2/2 Village des Pins close to Siesta Key

A modern kitchen layout is presented, featuring sleek white cabinetry and a spacious island with seating for two. Stainless steel appliances are visible, and ample counter space enhances functionality. Bright lighting illuminates the room, promoting a welcoming environment for meal preparation.

4.94 out of 5 average rating, 18 reviews

2025 Remodeled private villa, 6 min walk to beach

A serene outdoor space is showcased, featuring lush green palm and banana trees gently swaying near a calm body of water. Sunlight reflects off the water's surface, surrounded by a natural landscape of tall grasses and distant trees under a clear blue sky.

4.77 out of 5 average rating, 117 reviews

Lakefront 2BR • Perfect for IMG & Long Stays

Luxury villa rentals

A sunlit wooden deck is lined with blue lounge chairs, facing the expansive sandy beach and the Gulf of Mexico. Gentle waves can be seen lapping at the shore, under a sky filled with fluffy clouds. The inviting atmosphere offers direct access to the beach.

A Wave From it All managed by Beach Retreats

4.98 out of 5 average rating, 45 reviews

Beachfront Paradise! Ground level with Heated pool

4.85 out of 5 average rating, 53 reviews

An outdoor dining area features a large rectangular table with seating for eight, complemented by a shaded lounge space. A heated pool is visible, along with a sunken hot tub and sun loungers. Lush greenery surrounds the area, providing a serene backdrop.

Villa in Arlington Park

Relaxation awaits in this bohemian inspired villa

A spacious outdoor area features a heated pool with a sun shelf, surrounded by lounge chairs and a dining table. Lush greenery and palm trees provide shade, while a pink umbrella adds a pop of color. A sandy pathway leads toward the house, creating a welcoming environment.

Villa in Anna Maria

Bean Point Residence Unit A by SeaBreeze Vacation

Luxury Villa · Heated Pool & Spa · Steps to Beach

5 out of 5 average rating, 12 reviews

A spacious waterfront home is surrounded by green landscaping, palm trees, and open blue skies. A large heated pool is visible in the backyard, adjacent to a well-maintained deck. Comfortable seating is positioned on the sandy area by the water, providing a relaxing atmosphere.

Villa in Osprey

Paradise with a pool, pier and private beach area

A backyard view highlights a heated pool surrounded by vibrant green grass. Lounge chairs are positioned by the poolside, and a shaded dining area is set with a table and chairs. Tropical trees and landscaping frame the open space, creating a private oasis.

4.68 out of 5 average rating, 113 reviews

Cheerful 4-bedroom Villa with heated pool.

An aerial view of a heated swimming pool surrounded by tropical landscaping. Eight lounge chairs are positioned around the pool area, offering ample space for relaxation. The pool's clear water reflects sunlight, creating a serene atmosphere. A nearby structure with a silver roof complements the setting.

Villa in Anna Maria

4.61 out of 5 average rating, 31 reviews

Bayfront Bliss! Pool, BBQ and Dolphin Views!

Villa rentals with a pool

5 out of 5 average rating, 5 reviews

Lilo & Stitch Ohana Villa | Heated Pool Sleeps 12

An inviting outdoor space features a private pool surrounded by a screened enclosure. Sun loungers line the deck, while views of the serene lake and lush greenery are prominently visible through the transparent screens, creating a peaceful atmosphere for relaxation.

4.88 out of 5 average rating, 8 reviews

Villa Bookelia - 4 Bedroom Pool Home

A charming single-story villa is visible, featuring a red-tiled roof and large front windows. Lush greenery frames the entryway, while a spacious paved driveway accommodates several vehicles. Two bicycles are parked nearby, suggesting accessibility to outdoor activities and nearby attractions.

5 out of 5 average rating, 3 reviews

Siesta Key Beach Villa

Siesta Key Beach House

A modern home is depicted, featuring a light exterior with multiple large windows and an inviting entrance. Lush greenery and landscaped gardens frame the property, providing a serene atmosphere. A spacious driveway leads up to the house, complemented by a clear blue sky.

Villa Summerwind 3bed/2bath pool villa

A single-story home is set amidst lush landscaping and palm trees. The exterior features a light green color with a covered front porch. A stone-paved driveway leads to the entrance, surrounded by neatly arranged white gravel and vibrant greenery.

4.93 out of 5 average rating, 55 reviews

Palm Paradise: Near Beach, Heated Salt Water Pool

A bright and airy living room features a spacious gray sofa, accented by two side tables with lamps. A ceiling fan circulates air above. A large window with light filtering curtains allows natural light, with patio doors leading to the outdoor area. Decorative elements include a vibrant blue cabinet.

4.5 out of 5 average rating, 4 reviews

2bed/2bath steps away from Siesta Key beach!