Villa holiday rentals in Siesta Key

4.9 out of 5 average rating, 233 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, 27 reviews

Sunshine Get Away! 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.

4.9 out of 5 average rating, 173 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

AUG SALE! 1 min to beach, New, PETS OK!, 2Br/2BTH

EXCLUSVE CASEY KEY beach just .5 mi. away!! Sarasota 10 mins away! Pets total weight under 50 pounds welcome! Miles of uncrowded beach! Two KING beds.The Villa is a short 1 minute drive from Casey Key Beach! Two 55" 4K T.V's. New appliances and furnishings throughout! Kayaking, biking, boating minutes away. Lush tropical backyard and fire pit. 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!

4.98 out of 5 average rating, 42 reviews

A spacious outdoor living area features a grid of screens and glass, providing a view of the pool. A table surrounded by wicker chairs sits nearby, complemented by a barbecue grill. Light reflects off the water, while vibrant landscaping can be seen through the windows.

Villa in Gillespie Park

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.

4.88 out of 5 average rating, 297 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-near beaches-historical area- Pets welcome

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

4.98 out of 5 average rating, 131 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

4.93 out of 5 average rating, 75 reviews

Siesta Key*PRIVATE BEACH*Gulf Side*Heated Pool

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

4.83 out of 5 average rating, 93 reviews

The exterior of a single-story home is showcased, featuring a covered entryway with double doors. Lush greenery, including potted palm trees and trimmed shrubs, frames the entrance. A concrete path leads through a pebble-strewn area, offering a welcoming appearance on a sunny day.

Villa in Lake Sarasota

Paradise Villa- Sarasota

Relax with the whole family at this peaceful place to stay. Lovely furnished 3/2 home, freshly remodeled. Heated swimming pool. Great location to the word famous top-rated beaches -Siesta and Lido Key. UTC mall, restaurants, great shopping, golfing, Jungle Garden, aquarium, The John and Marble Museum of art and much more. The pool can be heated on request 72 hours notice is required and a pool heating fee of $35 per day plus tax must be paid prior to check in.

4.92 out of 5 average rating, 12 reviews

Two light blue adirondack chairs and a small table are positioned by a dock along the intercoastal waterway. The clear sky and calm water reflect greenery and colorful coastal homes in the background, creating a relaxing outdoor setting.

Villa in Longboat Key

Waterfront Condo, Close to Beach, with Boat Dock!

BEACH, BOAT, BIKE, FISH, KAYAK, TV/SPORTS, ENTERTAINMENT, FOOD, RELAX & ENJOY! Nestled between the highly sought after Anna Maria Island and St. Armand's Circle this amazing Longboat Key Boathouse offers just as much enjoyment as it does relaxation. This direct waterfront ground floor condo, packed with amenities, is just minutes away from the Gulf of Mexico. Come walk out of your back door to the intercoastal waterway, fish or sit and enjoy the tranquility.

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, 24 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.

4.86 out of 5 average rating, 109 reviews

The living room is designed with a neutral color palette, featuring a large screen TV mounted on the wall. A blue sofa and yellow armchair provide comfortable seating, while a stylish coffee table sits at the center. Natural light enhances the welcoming atmosphere.

Villa in Laurel Park

Quiet Downtown Sarasota Villa. 2 bed 2 bath. 644

Enjoy a stylish experience at this centrally-located attached villa, in the heart of Laurel Park, in downtown Sarasota. 2 bedrooms and 2 bathrooms. All the modern conveniences including a new 75" smartTV, kitchen, private yard & free parking. Ground floor villa offering 2 bedrooms & 2 bathrooms. Bedroom 1 has a king sized bed, Bedroom 2 has 2 twin beds & the living room has a pull out sleeper sofa. BBQ available out back for grilling. Updated 2023.

4.98 out of 5 average rating, 65 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 villa rentals in Siesta Key

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Private villa rentals

5 out of 5 average rating, 22 reviews

An outdoor pool is featured, surrounded by a spacious deck with lounge chairs. A hot tub is adjacent to the pool, and a waterfront view includes a wooden pier extending into the water, framed by lush greenery and a clear blue sky.

Villa in Palmetto

The Sea House

A modern living space is shown, featuring a comfortable black sofa and a cozy area rug. A large television is mounted on a stylish media unit, with light streaming in from nearby windows. A dining area with a small table and chairs is also visible.

5 out of 5 average rating, 44 reviews

Cheerful 2 bd 2 bt Villa close to Siesta Key Beach

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.

4.98 out of 5 average rating, 41 reviews

Vacation Villa/Resort Pool 4 miles to Siesta Key

5 out of 5 average rating, 3 reviews

Villa in Nokomis

Charming 1-Bedroom Villa

An aerial view captures a residential street lined with tropical greenery, showcasing a single-level home surrounded by lush palm trees. A spacious driveway leads to the property, which is flanked by neighboring homes, enhancing the tranquil atmosphere of the area.

4.83 out of 5 average rating, 6 reviews

Palm Haven Beach Side Villa

4.67 out of 5 average rating, 3 reviews

Villa

Villa Summerwind 3bed/2bath pool villa

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.

4.91 out of 5 average rating, 23 reviews

2025 Remodeled private villa, 6 min walk to beach

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.

4.67 out of 5 average rating, 12 reviews

Modern 3BR 2nd-Floor | Balcony | Pool

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.

4.88 out of 5 average rating, 8 reviews

Lautus Villa

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

Villa in Pass-a-Grille Beach

A collection of images showcasing Serenity. A close-up of seashells arranged on a decorative surface is featured, alongside a view through large windows framing lush palm trees and the beach. The living area presents comfortable seating, and a sunset view highlights the villa's exterior against a vibrant sky.

5 out of 5 average rating, 5 reviews

Private Beach Villa | Charming Decor | Sunset View

Villa in Longboat Key

Beach Castle LBK, Bayfront, Walk to Beach

A private patio area is displayed with a round table surrounded by six chairs and a large umbrella. Two lounge chairs are positioned nearby. The exterior features large windows reflecting a vibrant sunset, enhancing the tranquil atmosphere.

5 out of 5 average rating, 27 reviews

Seaside Inn a waterfront in Paradise

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!

A bright living area showcases a spacious sectional sofa with accent pillows, complemented by a patterned area rug. Large glass doors provide a view of the outdoor pool area, while artwork adorns the walls, enhancing the room's coastal ambiance. A foosball table is also visible.

4.69 out of 5 average rating, 13 reviews

Villa Oasis in the heart of Siesta Key with pool

A spacious balcony is featured, showcasing outdoor seating arrangements with a table and four black chairs, complemented by a lounge chair. The ceiling is adorned with wooden beams, and palm trees and the ocean are visible in the background, inviting a relaxed atmosphere.

4.88 out of 5 average rating, 104 reviews

Penthouse Oceanview Mermaid Villa

Villa rentals with a pool

Village West in heart of Siesta

4.78 out of 5 average rating, 27 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)

4.75 out of 5 average rating, 4 reviews

Sarasota downtown Beach getaway

Villa in Venice

Venice Golden Sunset Villa

5 out of 5 average rating, 4 reviews

Sarasota Villa with Pool Access Tennis Near Beach

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.

4.77 out of 5 average rating, 26 reviews

Remodeled Mid-century POOL house

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