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Villa holiday rentals in Lido Key

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Top-rated villa rentals in Lido Key

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Guest favourite
Villa in Sarasota
4.92 out of 5 average rating, 37 reviews

3685 White Pine Court, Sarasota, Florida

Village Des Pins is park like setting with lakes,pine trees, oversized heated pool,Jacuzzi,2 lighted tennis courts, Basketball court, shuffleboard,putting green and picnic area with grills. Located just minutes from white sand Siesta Key Beach - voted the best beach in USA, Westfield shopping mall with 140 stores, restaurants, movie complex and food court. This 2 bedroom/ 2 bath, very spacious villa with attached 1 car garage is very clean, comfortable, turn-key furnished with screened in lanai.

Guest favourite
Villa in Siesta Key
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

Guest favourite
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
4.92 out of 5 average rating, 162 reviews

DEC 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...:)

Guest favourite
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 Sarasota
4.87 out of 5 average rating, 128 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!

Guest favourite
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 Sarasota
4.9 out of 5 average rating, 223 reviews

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!

Superhost
Villa in Sarasota
4.67 out of 5 average rating, 9 reviews

Villa Siesta II -Dwntn Secret & pool near beaches!

Villa Siesta II! a little Paradise ,moments to downtown, private,pristine & very quiet. INSIDE- Granite, marble, mother of pearl, updated lighting- appliances.& 3 beds-3 t.vs . Outside Serenity (but excitement nearby) tropical foliage ,bromeliads, garden atrium bathroom. Singing birds ,wind chimes & Breakfast in your private patio ! We have dozens of stellar reviews but fewer since all guests have been multi month! Current guest is here May-Dec! JAN 2026 PROMO avail. Message for details

Guest favourite
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 Sarasota
4.97 out of 5 average rating, 39 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.

Top guest favourite
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 Sarasota
4.88 out of 5 average rating, 295 reviews

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

Top guest favourite
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 Sarasota
5 out of 5 average rating, 120 reviews

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

Guest favourite
A modern living area is visible, featuring a spacious sofa paired with a low coffee table. Large glass doors open to the waterfront view, allowing natural light to fill the space. A dining area with a marble table and elegant chairs is positioned nearby, accentuated by a stylish chandelier.
Villa in Sarasota
4.98 out of 5 average rating, 56 reviews

Waterfront Condo w/ Kayaks, Resort Pool, Sarasota

Indulge in serenity and style with this tranquil waterfront haven. Enjoy incredible views, a central location, and top-notch amenities! This luxurious condo boasts spacious interiors, contemporary finishes, and a balcony offering mesmerizing waterfront vistas. Proximity to restaurants, beaches, shopping, and more. Direct access to the Gulf, allows you to savor stunning Sarasota sunsets or bask in the beauty of the bayfront. Unwind and make the most of this exceptional retreat!

Guest favourite
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.
Villa in Sarasota
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

Guest favourite
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.
Villa in Sarasota
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

Popular amenities for villa rentals in Lido Key

KitchenWifiPoolFree parking on premisesAir conditioning

Private villa rentals

Villa in Bradenton
5 out of 5 average rating, 3 reviews

Lilo & Stitch Ohana Villa | Heated Pool Sleeps 12

Guest favourite
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.
Villa in Sarasota
4.8 out of 5 average rating, 35 reviews

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

Guest favourite
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
4.89 out of 5 average rating, 27 reviews

Northshore BeachHouse West Anna Maria Island

Guest favourite
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.
Villa in Sarasota
5 out of 5 average rating, 38 reviews

Cheerful 2 bd 2 bt Villa close to Siesta Key Beach

Superhost
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.
Villa in Sarasota
4.73 out of 5 average rating, 11 reviews

Charming 2/2 Village des Pins close to Siesta Key

Superhost
Villa in Siesta Key
5 out of 5 average rating, 4 reviews

The Citrus Hideout – SK Collection

Guest favourite
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.
Villa in Bradenton
4.77 out of 5 average rating, 117 reviews

Lakefront 2BR • Perfect for IMG & Long Stays

Superhost
An outdoor area features a lighted splashpad at the center, surrounded by pavers and tropical landscaping. Lounge chairs are positioned nearby, offering a relaxing spot to enjoy the serene atmosphere as soft lights illuminate the garden under a sunset sky.
Villa in Sarasota
4.9 out of 5 average rating, 52 reviews

Coastal Villa w/ Amazing Courtyard - Splash Pad!

Luxury villa rentals

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

Villa in Bradenton Beach
4.81 out of 5 average rating, 32 reviews

Short walk to the beach-Unit A

Superhost
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.
Villa in Holmes Beach

A Wave From it All managed by Beach Retreats

Guest favourite
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 Sarasota
4.84 out of 5 average rating, 51 reviews

Relaxation awaits in this bohemian inspired villa

Superhost
Villa in Sarasota

Waterfront Villa, private saltwater pool/hot tub

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.
Villa in Sarasota
4.69 out of 5 average rating, 112 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!

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.
Villa in Siesta Key
4.64 out of 5 average rating, 11 reviews

Villa Oasis in the heart of Siesta Key with 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

Top guest favourite
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.
Villa in Sarasota
4.97 out of 5 average rating, 38 reviews

Vacation Villa/Resort Pool 4 miles to Siesta Key

A contemporary living area features a comfortable gray sofa and a round marble coffee table. Natural light flows in through sliding glass doors that lead to the outdoor space. A dining area with white chairs is positioned next to the kitchen, enhancing the open concept design.
Villa in North Port
4.86 out of 5 average rating, 86 reviews

Luxurious Family Villa with pool 29 min the beach

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

A sparkling pool is featured within a screened-in area, surrounded by brick pavers. Comfortable lounge chairs are positioned beside the water, while a dining table with chairs is visible in the shaded area. Lush greenery is present in the background, enhancing the outdoor setting.
Villa in Bradenton
5 out of 5 average rating, 4 reviews

Florida Villa Sunrise - 4 Bedroom Home with Pool

Superhost
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 in Bradenton

Villa Summerwind 3bed/2bath pool villa

Guest favourite
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.
Villa in Sarasota
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.
Villa in Sarasota
5 out of 5 average rating, 3 reviews

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

Destinations to explore

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  3. Florida
  4. Sarasota County
  5. Sarasota
  6. Lido Key
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