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Villa vacation rentals in Longboat Key

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Top-rated villa rentals in Longboat Key

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Top guest favorite

Lush greenery frames the entrance of the villa, featuring vibrant yellow flowers and neatly trimmed hedges. Soft light filters through the palm leaves, creating a serene pathway leading to the inviting entryway, surrounded by a tropical landscape.

Villa in Sarasota

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.

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, 158 reviews

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...:)

A stylish entrance is framed by lush palm trees and neatly arranged greenery. A stone pathway leads to a spacious front porch with modern railings and a prominent double door, presenting an inviting first impression of the villa.

4.89 out of 5 average rating, 19 reviews

Luxury Pool Villa in Upscale Tampa Centrally Loctd

Surround yourself in this spacious, 3500 sf of luxurious finishes for your party to relax comfortably in. 5 Bedrms 5 Bath villa is the perfect choice. Heated Pool & outdoor entertainment awaits you. Stunning equipped kitchen, spa like bathrooms, and cozy bedrooms will astound you. The master bedroom features a king-sized bed & the other three bedrooms offer queen bed, two full-size beds & pair of twin size beds. Busch Gardens: 8min / Downtown: 17min / USF: 8min / Clearwater: 45min / Orlando :1hr

A sandy pathway leads through palm trees and lush greenery toward a wide beach. The ocean's calm surface reflects a bright blue sky with scattered clouds. A beach umbrella is visible to the left, suggesting a serene, inviting atmosphere.

Villa in Redington Shores

4.91 out of 5 average rating, 125 reviews

1 house to beach entrance. Peaceful. Walk to dine.

Amazing location tucked on quiet street beachside, Washer/Dryer IN UNIT, Central AC, WIFI, Free parking, beach supplies. 1 of 3 units in peaceful beachside villa. Private retreat away from busy condos. Short walk to restaurants Wide, pristine beach goes for miles 1 king bed 2 bedrooms. 3rd bedroom is BONUS ROOM/laundry 2 twin beds & sliding door ***PLEASE NOTE: WORKERS PRESENT IN LOWER UNITS 9A-5P weekdays thru April 30th. Other work in neighborhood possible. Contact host w/questions

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

4.85 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!

Top guest favorite

A spacious living room features a large sectional sofa adorned with green pillows and a coffee table placed on a vibrant area rug with palm leaf designs. A flat-screen TV is mounted on the wall, complemented by decorative accents and artwork throughout.

Villa in Safety Harbor

5 out of 5 average rating, 133 reviews

Villa Key West "Villas by Christine"

Perfect location, Charming Villa Guests are loving the newly renovated Villa Key West. Christine's goal was to make guests to feel the charm of a Key West Villa while experiencing the amenities of a 5 star hotel The Living room and bedrooms have large smart TV’s with complementary Roku, Netflix, Prime and Hulu. Enjoy the view out back of one of Safety Harbors 150 year old Oak & nature pond. We are per friendly. Please let us know you will be bringing pet. Pet fee of $100.00 due upon arrival.

A bright and inviting bedroom features two twin beds adorned with a coastal-themed bedspread. Large windows allow natural light to fill the space, framed by turquoise curtains. A bedside table with lamps sits between the beds, complemented by cheerful nautical decorations on the walls.

Villa in Sarasota

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

Villa in Lido Key

4.89 out of 5 average rating, 202 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!

The villa's exterior is framed by lush greenery, showcasing a spacious garden area. A large tree provides shade near the screened-in porch, where outdoor living can be enjoyed. The well-maintained lawn is vibrant under bright blue skies, enhancing the relaxing outdoor environment.

Villa in Siesta Key

4.82 out of 5 average rating, 68 reviews

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.

A bright bedroom features a spacious bed with a patterned coverlet and decorative pillows. Two lamps provide soft lighting on either side, while a ceiling fan hangs above. Sliding glass doors with vertical blinds lead to an outdoor area, complemented by neutral carpeting.

Villa in Sarasota

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.

A modern kitchen area features sleek white cabinetry, gray countertops, and stainless steel appliances. An island with two black stools offers additional seating. Well-lit by overhead fixtures, the space includes a door leading to an entrance and a doorway to a small adjacent room.

4.88 out of 5 average rating, 146 reviews

Boho -Minimalist villa

Welcome to our Boho Minimalist Villa 4311 unit B with a 2 bedroom and 1 bathroom. Conveniently located in the heart of Tampa, Florida. “Points of interest” to visit and enjoy while you are here: Raymond’s James Stadium, New York Yankees Training Camp, Hillsborough Community College, International Tampa Airport, Downtown Tampa, Midtown within less than 10-minutes’ drive enjoy a great afternoon eating at many local restaurants.

A tranquil pool area is highlighted by a sparkling blue water surface, surrounded by lush greenery. Comfortable lounge chairs are arranged nearby, adorned with striped pillows. A gentle waterfall feature adds a serene touch, while a privacy fence encloses the space.

5 out of 5 average rating, 27 reviews

(BAYC) Heated Pool Villa. Boat rental available

Discover pure luxury at our centrally-located 4-bedroom contemporary pool villa. Unwind in the game room with billiards and a 3000-game arcade machine. Engage in chess on our custom table or lounge by the pool on comfy chairs and hammocks. Delight in outdoor dining with a tranquil poolside fountain. This lavish retreat offers modern comfort and endless entertainment. Book now for an unforgettable getaway.

Vacation rentals for every style

Get the amount of space that is right for you

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Quaint homes, peaceful surroundings

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A space thats all yours, with room for everyone

Popular amenities for Longboat Key villa rentals

Free parking on premises

Air conditioning

Private villa rentals

Top guest favorite

Villa in Indian Rocks Beach

5 out of 5 average rating, 17 reviews

IRB Harbor House Semiprivate Waterfront Pool Villa

The dining area features a modern table with gold accents, surrounded by plush gray chairs. A stylish chandelier hangs above, illuminating the space. The open-concept layout offers a clear view of the adjacent kitchen and a spacious living area with a large television.

Villa in Palm Harbor

4.91 out of 5 average rating, 33 reviews

Villa Luxe~Heated Saltwater Pool~Near Beaches

Top guest favorite

A screened-in outdoor seating area is featured, furnished with a large sectional sofa adorned with red accent pillows. A low coffee table holds a bowl of fresh fruit and drinks, overlooking a sparkling pool surrounded by lush greenery.

Villa in Sarasota

4.97 out of 5 average rating, 59 reviews

SEALAND 3/2 Modern Villa w/ Pool near Siesta

A cozy living area features a dark gray sofa adorned with colorful cushions. A vibrant area rug sits beneath a rectangular coffee table. Bright orange chairs add a pop of color, while a large mirror and framed artwork enhance the space's brightness.

Villa in Clearwater Beach

4.91 out of 5 average rating, 222 reviews

V3- 1 BR, waterfront villa, 2 min walk 2 beach

A spacious outdoor area featuring a pool surrounded by lounge chairs. Lush greenery and palm trees enhance the setting, while a nearby area is prepared for games. A light-colored non-slip surface provides a safe space for relaxation and enjoyment under the clear sky.

Villa in Bradenton

4.87 out of 5 average rating, 97 reviews

Florida Living

A fire pit made of stone is surrounded by two white adirondack chairs. Flames rise energetically from the center, surrounded by logs in a gravel setting. Lush green plants are visible in the background, creating a cozy outdoor ambiance.

Villa in Sarasota

4.86 out of 5 average rating, 37 reviews

The Olive Turtle

A spacious living area is highlighted by a stone fireplace and large glass doors that open to a serene outdoor space. Wicker furniture includes a comfortable sofa and armchairs, complementing the warm, neutral tones of the walls and flooring.

Villa in Siesta Key

4.91 out of 5 average rating, 161 reviews

Mermaid Villa Ocean Front!

A shaded outdoor seating area features two wicker chairs surrounding a small table, set against a backdrop of a brick wall and a light-colored building. The garage doors are visible, along with a partially covered patio area, creating a welcoming atmosphere.

Villa in Bayshore Beautiful

4.99 out of 5 average rating, 68 reviews

Southern Charm Villa with Pool

Luxury villa rentals

The charming exterior of a beautifully restored duplex features a welcoming entrance with decorative columns and a spacious balcony. Warm lights illuminate the facade, while lush greenery surrounds the property, creating an inviting atmosphere complemented by the architectural details typical of the historic Ybor City neighborhood.

Villa in Ybor City Historic District

4.94 out of 5 average rating, 18 reviews

Luxury 5BR Ybor City Duplex Near 7th

Villa in Clearwater

4.95 out of 5 average rating, 39 reviews

Clearwater Villa Heated Pool, Golf, 4K Projector

A serene outdoor space features a circular fire pit surrounded by several adirondack chairs. Lush greenery and trees frame the area, while a vibrant sunset paints the sky in soft pastel hues. The lake is visible in the distance, enhancing the peaceful ambiance.

Villa in Thonotosassa

4.95 out of 5 average rating, 41 reviews

Lakeside Villa

A wooden deck leads down to a lush green area with artificial turf, adjacent to a tranquil canal. The water reflects the surrounding greenery and blue sky, creating a peaceful outdoor setting, ideal for relaxation.

4.85 out of 5 average rating, 62 reviews

Best deal in town!

The exterior of the villa is showcased under a sunset sky, featuring a two-story gray structure with large windows. The well-maintained lawn is complemented by shrubs and tropical plants, while a wooden fence marks the boundary of the property.

Villa in Seminole

4.86 out of 5 average rating, 22 reviews

5BR LUX Pool Villa | w/ Sauna | Near The Beach

A rooftop terrace is shown with two lounge chairs and a small table. A large umbrella provides shade, while a view of the waterfront and city skyline is visible in the background. The sky displays soft hues of purple and pink, enhancing the serene setting.

Villa in Clearwater Beach

4.96 out of 5 average rating, 25 reviews

4 min Walk to Beach, Pool, Roof Deck

A vibrant game room features colorful lighting and playful wall art. Various entertainment options are included, such as a foosball table, ping pong table, and lounge area. A refrigerator for refreshments is positioned alongside seating for relaxation.

4.89 out of 5 average rating, 36 reviews

Waterfront-6 BR-Heated Pool-Game Room-Fire Pit

Villa in Seminole

4.97 out of 5 average rating, 58 reviews

5 BR Luxury Beach Villa: Heated Pool & Games Room

Villa rentals with a pool

A screened lanai houses a private heated pool, surrounded by a spacious deck. Two chaise lounge chairs are positioned near the water, while a cozy seating area nearby invites relaxation. A green backdrop of lush vegetation enhances the tranquil outdoor setting.

Villa in North Port

4.83 out of 5 average rating, 24 reviews

Cheerful 3-bed villa with heated pool+beach staff

Villa in Dunedin

5 out of 5 average rating, 12 reviews

NEW Family Haven: Near Honeymoon Island

Villa in Venice

4.83 out of 5 average rating, 29 reviews

Peaceful bright home minutes from the beach

4.89 out of 5 average rating, 97 reviews

Solar Heated Pool Paradise/5mins 2 beach/Games/BBQ

A clear blue pool is surrounded by a decorative stone patio. Comfortable lounge chairs are positioned nearby, inviting relaxation. A covered outdoor dining area with a table and chairs is visible under a shaded awning. Lush greenery complements the serene atmosphere.

Villa in Sarasota

4.97 out of 5 average rating, 29 reviews

Luxurious Pool Retreat Near Siesta Key, Sarasota

Villa in Seminole

4.95 out of 5 average rating, 41 reviews

Modern Luxury Retreat - Heated Pool Spa, Game Room

Top guest favorite

5 out of 5 average rating, 71 reviews

Luxury home in the heart of South Tampa & POOL!

Villa in St. Petersburg

4.8 out of 5 average rating, 127 reviews

Dolphin Cove Waterfront St. Pete Beach w/ Pool

Quick stats about villa rentals in Longboat Key

Total rentals
10 properties
Nightly prices starting at
$100 before taxes and fees
Total number of reviews
300 reviews
Family-friendly rentals
10 properties are a good fit for families
Rentals with a pool
10 properties have a pool
Wifi availability
10 properties include access to wifi

Destinations to explore