Villa holiday rentals in Longboat Key

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...:)

Villa in Indian Rocks Beach

4.92 out of 5 average rating, 129 reviews

Heated Hybrid Pool~Modern Beach House~Walk 2 beach

Welcome to Sweet Serenity! A newly renovated modern beach house that comes with an endless amount of amenities including all your beach needs and a large brand new HEATED Hybrid Pool that has room for the whole family. Just pack your clothes & we will provide the rest. This home is perfect for your family vacation w/ a very open layout, tons of beach decor to get you in that island mood & 3 large bedrooms. Located in a quiet family friendly neighbourhood, a short, less than 10 min walk 2 beach!

The kitchen features modern cabinets with white finishes and granite countertops. A round dining table with four chairs is situated near a large window, allowing natural light to fill the space. Stainless steel appliances, including a full-size refrigerator, are arranged along the wall.

4.91 out of 5 average rating, 208 reviews

Busch Gardens, Moffitt, USF Charming Villa

Cozy 1 bedroom and 1 bathroom villa, completely renovated in Live Oaks Square. 3 minutes away from Busch Gardens, Adventure island, MOSI and USF. It is about 21 minutes from Tampa Airport. The back yard has been accommodated so you can enjoy every minute of your stay. -Tampa International Airport 15MI -Tampa Bay Buccaneers Stadium 8.0MI -Aquarium8.3MI -Busch Gardens1.6MI -Clearwater32MI -Adventure Island2.2MI -Epperson Lagoon23MI -James Haley Veterans2.9MI -USF3.2MI -Moffitt3.5MI -Publix4.1MI

4.9 out of 5 average rating, 218 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!

4.97 out of 5 average rating, 144 reviews

The exterior of the home is surrounded by lush tropical foliage, including palm trees and native plants. A covered patio area can be seen, leading to a pathway of gravel that weaves through the vibrant garden. The inviting entrance is framed by greenery, creating a serene atmosphere.

Villa in Largo

Quiet 3BD Huge Tropical Garden & Patio. 5min Beach

Escape to our tranquil tropical paradise! Our private garden overflows with emerald palm trees, exotic foliage and native blooms, while the covered patio offers a place to relax and savor nature's natural sounds. Grill area, outdoor seating, lounge chairs. 5 minutes to Indian Rocks Beach and downtown amenities. Embark on bike rides on the nearby Pinellas Trail and Tailor Park with our complimentary bikes. Enjoy fun and fishing with our provided kayaks and gear, easily loaded onto your car.

4.88 out of 5 average rating, 290 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, 115 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!

Villa in Indian Beach-Sapphire Shores

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.

4.98 out of 5 average rating, 55 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!

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, 172 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.

5 out of 5 average rating, 23 reviews

Villa in Holmes Beach

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!

5 out of 5 average rating, 112 reviews

A modern living area features a large black leather sectional sofa adorned with decorative pillows, complemented by a polished coffee table. Above, a flat-screen TV is mounted on a light-colored wall. Art pieces showcase scenic landscapes, and natural light filters in through white-shuttered windows.

Villa in Safety Harbor

Villa Italia "Villas by Christine"

Perfect location, Charming Villa!! Guests are loving the newly renovated Villa Italia. Two luxury Masters with separate bathrooms - one upstairs & one down. Within the upstairs bedroom you have a queen size bed along with a full size couch for lounging during the day. We are pet friendly. Please let us know you will be bringing your pet. Pet fee of $100. can be paid beforehand or is due upon arrival.

4.9 out of 5 average rating, 116 reviews

Villa in Largo

Heated Pool Paradise/Billiards/BBQ/5 min 2 Beach

Welcome to your private, tropical escape! Unwind by the solar-heated pool in a screened, 🚫🦟 mosquito-free lanai. FUN & GAMES: Enjoy Billiards 🎱, Foosball, games, and 3 Smart TVs 📺. PRIME LOCATION: Only 5 min 🚗 to Indian Rocks & Bellaire Beach, FL Botanical Garden, and dining. Essentials: 🌞 Heated Pool (Private!) 🎮 Game Room 🛏️ 4 Queen/Full Beds 🧺 Beach Amenities

Popular amenities for villa rentals in Longboat Key

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Private villa rentals

5 out of 5 average rating, 16 reviews

Villa in Siesta Key

The Beachwood Hideout | SK Collection

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, 38 reviews

Cheerful 2 bd 2 bt Villa close to Siesta Key Beach

4.68 out of 5 average rating, 65 reviews

A large heated swimming pool is surrounded by lounge chairs and tiki huts, set against the backdrop of a sandy beach and the shimmering Gulf waters. Sunlight reflects off the water, creating a tranquil atmosphere for relaxation and leisure.

Villa in Indian Shores

Relax just steps from beach & Gulf of America

A villa with a light-colored exterior features a spacious driveway made of pavers. Lush tropical landscaping adds color, while a large parking garage is visible on the right side. In the background, a multi-story building is partly shown under a partly cloudy sky.

5 out of 5 average rating, 9 reviews

Newly Remodeled Luxury Beach Villa on Siesta Key!

5 out of 5 average rating, 35 reviews

A charming exterior of a townhome is presented, featuring a bright red front door. Lush greenery and colorful plants frame the pathway leading to the entrance, with a well-maintained lawn inviting guests to explore. The surrounding area is dotted with additional townhomes.

Villa in Fox Chase

Coastal Cottage

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.

4.94 out of 5 average rating, 47 reviews

Coastal Villa w/ Amazing Courtyard - Splash Pad!

The living area features a green sofa adorned with decorative pillows, paired with a round coffee table on a jute rug. A warm brick fireplace complements the space, which opens up to the pool area through large windows framed by sheer curtains.

4.74 out of 5 average rating, 247 reviews

Perfect Location w/ pool -close to beach or DT!

5 out of 5 average rating, 18 reviews

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.

Villa in Siesta Key

Modern, Walkable, Updated, Private.

Luxury villa rentals

Villa in Indian Rocks Beach

An aerial view showcases a coastal neighborhood along the intracoastal waterway, featuring a single-story home with a gray roof and a landscaped front yard. Palm trees line the driveway, and nearby properties reflect a variety of architectural styles, emphasizing the serene waterfront setting.

5 out of 5 average rating, 38 reviews

IRB Harbor House Semiprivate Waterfront Pool Villa

4.98 out of 5 average rating, 47 reviews

Luxury 4-Bedroom Pool Retreat Near Siesta Key

4.96 out of 5 average rating, 48 reviews

An outdoor space features a circular fire pit surrounded by several black Adirondack chairs, all set on gravel. The background showcases a heated pool and spa, with a vibrant sunset sky illuminating the scene. The villa and dining area are visible, enhancing the inviting atmosphere.

Villa in Seminole

Modern Luxury Villa - Heated Pool Spa, Game Room

A serene outdoor pool area is enclosed by a screened structure, allowing for a private retreat. Sun loungers are positioned beside the clear, inviting water, and lush greenery surrounds the pool, enhancing the tranquil setting.

5 out of 5 average rating, 79 reviews

Luxury home in the heart of South Tampa & POOL!

Villa in Redington Shores

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.

4.92 out of 5 average rating, 138 reviews

1 House to beach! Peaceful beachside getaway

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

5 out of 5 average rating, 29 reviews

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.

Villa in Bay Crest Park

(BAYC) Heated Pool Villa. Boat rental available

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

Villa rentals with a pool

A covered outdoor area showcases a glowing blue pool, surrounded by sleek lounge chairs and a playful pool float. Glass sliding doors offer a view of the comfortable seating area, where a table and chairs provide an inviting space for relaxation.

4.84 out of 5 average rating, 50 reviews

Serene Heated Pool Oasis Tampa Vacation

4.96 out of 5 average rating, 23 reviews

A spacious heated saltwater pool is surrounded by a screened enclosure, featuring colorful inflatable floats. A playroom is visible with cheerful decor, while a cozy media room offers comfortable seating. The exterior showcases a welcoming home, with a yard perfect for children’s play.

Villa in Dunedin

Family Haven/Kid's Amenities Near Honeymoon Island

4.94 out of 5 average rating, 47 reviews

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

Villa Luxe~Heated Saltwater Pool~Near Beaches

4.8 out of 5 average rating, 49 reviews

A spacious pool area is highlighted, showcasing a turquoise pool surrounded by potted plants and tropical foliage. The villa's exterior features large windows that emit a warm glow, creating an inviting ambiance as dusk sets in.

Villa in Clearwater

La Villa, 1 of 3 rentals on-site, pool, near beach

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

4.75 out of 5 average rating, 20 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)

4.95 out of 5 average rating, 81 reviews

An outdoor space features a basketball hoop and a putting green, surrounded by fresh landscaping. A spacious covered area is seen in the background, providing shade. Palm trees and a clear blue sky enhance the inviting environment.

Villa in Seminole

Perfect location 6BR/4BA Pool GameRoom 5 min Beach