Villa vacation rentals in Siesta Key

An open living area features a gray sectional sofa paired with colorful throw pillows, a white circular coffee table, and a brown armchair. Large sliding doors provide views of the pool area, while natural light brightens the space through sheer white curtains.

4.93 out of 5 average rating, 15 reviews

Remodeled Mid-century POOL house

Enjoy the pool and the Beach ! NOW NO PET FEE! Close to Sarasota Center, only a 15-minute drive from Siesta Key Beach, the number one beach in the U.S. Enjoy nearby restaurants and the bike trail. Featuring a unique in-ground pool that is the showcase of the L-shaped courtyard. Featuring new beds and comfortable mattresses. 3 beds, 2 baths, the living space is open to the kitchen. The open family living room is filled with light. If you haven’t found your happy place yet, this could be the one!

4.92 out of 5 average rating, 160 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

OCT SALE! 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...:)

4.86 out of 5 average rating, 120 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!

4.9 out of 5 average rating, 217 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!

4.84 out of 5 average rating, 50 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

Welcome to Paradise Villa! Location is everything! Come vacation in this gorgeous new modern farmhouse, right in the heart of Sarasota. You’ll be just a short drive from the world famous Siesta Key Beach, Downtown Sarasota, and Lido Key Beach. Within walking distance is Morton’s Gourmet Market. Also featuring a new heated Pool, Hot Tub and Sunken Gas Fire Pit. For the “work from home” travelers we feature a work station and two independent sources of internet. FIOS & Starlink Satellite.

4.93 out of 5 average rating, 72 reviews

Siesta Key*PRIVATE BEACH*Gulf Side*Heated Pool

Beautifully updated villa conveniently located BEACH SIDE on Siesta Key/Crescent Beach. Short 3 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 & air mattress. FULLY equipped kitchen w/granite counters,2 new smart TV's,GORGEOUS bathroom w/8ft shower,screened lanai, & outdoor shower. Steps to heated community pool,laundry facilities & free trolly. Walk to Stickney Point Restaurants/Bars/Rentals/Marina

4.88 out of 5 average rating, 289 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, 114 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

Tropical Luxury Villa: 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 and blackout shades 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!

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.

4.85 out of 5 average rating, 137 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 private pool area is surrounded by tropical greenery, featuring a wooden deck with smooth steps leading down to the water. Bright lounge chairs sit nearby, and pool floats are casually draped over the railing, inviting relaxation and enjoyment.

4.76 out of 5 average rating, 117 reviews

5 min to Siesta Key, Heated Pool, Grill, WiFi

Welcome to 'Villa Tropicana' 'Villa Tropicana' is a 3BD/2BA home featuring a pool with a deck. Enjoy a beverage in the tropical front garden or sunbathe by the pool out back for a dream vacation. The best part is the location - less than 5 minutes away from the gorgeous beaches of the world famous Siesta Key. In case you need any additional information, please try prefix 941, followed by 376, and finally 8679. Thank you, Ven & The Hacienda Team

5 out of 5 average rating, 4 reviews

The Citrus Hideout – SK Collection

Winter season (Jan–Mar): 1-month minimum stays. Check-in/out on the 1st or last day of the month. Bright tropical condo with vibrant lime, orange, and red accents, 2 bedrooms, and 2 baths. Relax on the screened porch or gated patio. Walk 5 minutes to deeded beach access with chairs and towels or swim in the pool across the street at Aloha Kai. Assigned parking and trolley stop just 2 minutes away. Part of the SK Collection by Siesta Stays.

5 out of 5 average rating, 21 reviews

Beachfront Paradise! Ground level with Heated pool

Gulf-front getaway with unbeatable beach access—step out your back door and right onto the sand! Enjoy a king bed, queen sleeper, fully stocked kitchen, in-unit washer/dryer, and professional linen service. Beach towels, two chairs, and an umbrella are included. Relax or grill by the shared heated pool and soak in the stunning Gulf views. Everything you need for the perfect beach escape—just bring your sunscreen and unwind!

Popular amenities for Siesta Key villa rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Private villa rentals

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.

4.8 out of 5 average rating, 35 reviews

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

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.

5 out of 5 average rating, 36 reviews

Vacation Villa/Resort Pool 4 miles to Siesta Key

The exterior of the home features a well-manicured lawn and colorful landscaping. A bright red front door serves as a focal point against the neutral-colored facade. Palm trees and shrubs frame the entrance, complemented by a two-car garage on the right.

Villa in North Port

5 out of 5 average rating, 4 reviews

Family pool home near beaches & golf. May-June

An open-concept living area showcases a comfortable sofa and a modern coffee table, surrounded by large windows offering views of the patio. A dining area is visible, leading to a sleek kitchen equipped with stainless-steel appliances. Ceiling fans and recessed lighting provide ambient illumination.

Villa in Venice

5 out of 5 average rating, 3 reviews

Luxury house with huge patio

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.

4.7 out of 5 average rating, 10 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.

4.76 out of 5 average rating, 107 reviews

Mi Pequeña Casa - 2/2 on a lake

The image showcases a large swimming pool surrounded by a paved patio, featuring multiple lounge chairs positioned along its perimeter. Umbrellas provide shade while trees and green foliage create a natural backdrop under a clear blue sky.

5 out of 5 average rating, 32 reviews

NEW-Cheerful 2-bedroom villa-13 min. to Siesta Key

Luxury villa rentals

A serene outdoor area features a newly renovated salt swimming pool accompanied by a jacuzzi. Lush greenery and tropical plants surround the space, offering privacy. A comfortable seating arrangement is positioned beside the pool, enhancing the outdoor experience.

Lautus Villa

A bright living area features a grey sleeper sofa adorned with colorful cushions. A round coffee table is positioned in the center, surrounded by a dining table with black chairs. The kitchen is equipped with stainless steel appliances and vibrant tile backsplash, enhancing the modern decor.

4.81 out of 5 average rating, 37 reviews

Beachside Bliss! With Pool, Near Beach and

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.

4.61 out of 5 average rating, 28 reviews

A Wave From it All managed by Beach Retreats

A serene outdoor pool area is surrounded by lush tropical foliage. Soft lighting is present along the pool's edge, enhancing the relaxing environment. Two lounge chairs are positioned nearby on a patterned stone deck, providing a tranquil spot for relaxation.

Villa in Anna Maria

North Beauty/pool deal 2Master x4 pax+ 25PP PN

4.35 out of 5 average rating, 34 reviews

2bedroom/2bath steps away from siesta key beach!

4.89 out of 5 average rating, 38 reviews

Heated Pool & Spa • Outdoor Kitchen/Theater/Games

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

The outdoor area features a private pool surrounded by a paved patio and lush greenery. Two lounge chairs are positioned near the pool, and an outdoor dining table with umbrella is visible, providing a shaded space for meals or relaxation.

4.5 out of 5 average rating, 8 reviews

Welcoming 3BR 2nd-Floor | Balcony | Pool

Villa rentals with a pool

The outdoor lanai features a screened enclosure with a private swimming pool. Two lounge chairs are positioned near the pool's edge, accompanied by a colorful pool float. Lush greenery surrounds the area, providing a serene backdrop under a partly cloudy sky.

Villa in North Port

4.85 out of 5 average rating, 26 reviews

Cheerful 3-bed villa with heated pool+beach staff

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

An outdoor area features a spacious patio with a large dining table and several chairs, set among lush tropical greenery. A pool is visible nearby, surrounded by lounge chairs. A spiral staircase leads to an upper level, adding architectural interest to the space.

Villa in Anna Maria

4.71 out of 5 average rating, 7 reviews

Bean Point Residence Unit B by SeaBreeze Vacation

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.

4.86 out of 5 average rating, 7 reviews

Villa Bookelia - 4 Bedroom Pool Home

5 out of 5 average rating, 8 reviews

An inviting screened lanai features a heated swimming pool surrounded by a spacious deck. Comfortable lounge chairs are positioned beneath a large umbrella, and lush greenery is visible through the transparent enclosure, providing a serene atmosphere for relaxation.

Villa in Venice

VIlla Venice

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 spacious living area is furnished with a sectional sofa and a wooden coffee table, surrounded by large windows that allow natural light. Rattan chairs are placed nearby, with indoor plants adding a touch of greenery. Decorative accents enhance the beach-themed decor.

4.54 out of 5 average rating, 13 reviews

Welcome to Casa Covella in Polynesian Gardens

The exterior of a modern beachfront home is depicted, featuring a light blue facade with white trim. Lush palm trees and neatly maintained landscaping surround the entrance, and a driveway with pavers leads to the garage areas below. A staircase on the right leads to the home's elevated entrance.