Villa holiday rentals in Longboat Key

4.91 out of 5 average rating, 167 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

APRIL OPEN 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...:)

4.85 out of 5 average rating, 141 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!

4.94 out of 5 average rating, 140 reviews

An outdoor patio area features a dining table adjacent to a heated pool. Lounge chairs are positioned nearby, under a screen enclosure. The pool is framed by a laid stone surface, with a view of lush greenery beyond the surrounding fence.

Villa in St. Petersburg

Heated Pool! Huge Walk In Shower! 5 min to beach!

Welcome to Coastal Paradise! This modern villa is newly remodelled and professionally furnished with a beautiful coastal theme. It has a very spacious open layout with plenty of space for the whole family. A huge master walk in shower with two shower heads and four body jets! Out back is a private heated pool with lounge chairs, grill, a hammock, corn hole and a beautiful patio set to enjoy a meal outdoors. Madeira beach is only a 5 min drive away! We also provide all your beach necessities!!

4.9 out of 5 average rating, 226 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, 157 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, 296 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, 122 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

Villa in Redington Shores

4.91 out of 5 average rating, 144 reviews

Beach 1 house away Walk to dine. 2 King 2 twin

1 of 3 units in a small villa Gulf side. Walk to restaurants. 30 second walk to gorgeous beach with amazing sunsets and miles of beachfront. Tucked away on a quiet street, a hidden gem away from busy condos. Beach towels, chairs & cooler. Washer/Dryer in unit, central AC, Wi-Fi, free parking in front. This unit features 2 bedrooms with King beds and 1 bedroom with 2 Twins (this bedroom has additional sofa and washer/dryer). Blackout curtains & comfy mattresses in all bedrooms.

4.9 out of 5 average rating, 125 reviews

Villa in Largo

The Tropical Oasis, w/ Solar Heated Pool and Games

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

A saltwater pool is featured with a large yellow inflatable duck wearing sunglasses. Water splashes create a lively ambiance, while a shaded patio area is visible in the background. Roller coasters can be seen beyond the pool area, highlighting the proximity to attractions.

4.91 out of 5 average rating, 135 reviews

Busch Gardens Deluxe Edition w/heatedpool

Accommodation that you choose can make a big difference to your trip. Busch Gardens Royal Experience offers an exciting villa taking your adrenaline limit to the next level. Get out of that overwhelming routine. Create extraordinary memories in this full renovated house 3bedrooms/2bathrooms located 3 minutes away of Busch Gardens Tampa Bay. From its cozy pool area with a majestic pergola you can see several roller coasters. Just a VIP experience so Put it slow motion.

4.86 out of 5 average rating, 138 reviews

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 Southgate

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

4.77 out of 5 average rating, 183 reviews

A spacious saltwater pool stretches across the backyard, bordered by a paved area featuring lounge chairs. Lush greenery, including palm trees and a nearby canal, enhances the serene outdoor setting under a clear blue sky.

Villa in St. Petersburg

Dolphin Cove Waterfront St. Pete Beach w/ Pool

THIS is the Florida life! A private oasis with a stunning tropical backyard and an oversized SALTWATER pool. Enjoy 140+ ft of waterfront on Bear Creek canal, where manatees and dolphins visit daily! Kayak just 15 minutes to nearby islands. Beaches are a quick 7-minute drive, downtown is 15 minutes away, and shops/restaurants are right across the street. The home is simple and unupdated, but the backyard is a true paradise you won’t forget!

Popular amenities for villa rentals in Longboat Key

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Private villa rentals

4.92 out of 5 average rating, 53 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

4.83 out of 5 average rating, 89 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

4.89 out of 5 average rating, 28 reviews

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

Northshore BeachHouse West Anna Maria Island

5 out of 5 average rating, 7 reviews

A shaded outdoor seating area features a dark wicker table with matching chairs, positioned on a decorated patio. Lush greenery and water views are visible beyond, enhancing the serene atmosphere. The space is designed for relaxation and offers a scenic spot to enjoy the surroundings.

Villa in Nokomis

Dockside 1-Bed Villa

4.76 out of 5 average rating, 55 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 4 rentals on-site. Heated Pool!

4.89 out of 5 average rating, 35 reviews

A comfortable living and dining area is showcased, featuring a glass dining table with white wooden chairs. A cozy sectional sofa is arranged around a coffee table, with a rug underfoot. Natural light filters through two windows, complemented by decorative artwork on the walls.

Villa in South Sarasota

Robinhood Beach Villa near Siesta Key Beach!

4.77 out of 5 average rating, 129 reviews

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 South Bradenton

Lakefront 2BR • Perfect for IMG & Long Stays

A comfortable living area features a gray, U-shaped sectional sofa accompanied by a center coffee table. Natural light brightens the space, highlighting the light-colored tile flooring. The open layout connects the living area to a kitchen visible in the background.

4.93 out of 5 average rating, 41 reviews

Fully renovated villa on Siesta Key

Luxury villa rentals

4.97 out of 5 average rating, 33 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

4.98 out of 5 average rating, 45 reviews

An outdoor patio area features a private pool surrounded by a spacious deck. A seating arrangement with chairs and a table is positioned nearby, along with a sauna. The setting is complemented by lush green grass and a colorful sunset sky.

Villa in Seminole

[TRENDlNG] Modern 5BR Pool Villa + Arcade & Sauna

5 out of 5 average rating, 4 reviews

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.

Villa in St. Pete Beach

Private Beach Villa | Charming Decor | Sunset View

Villa in Indian Rocks Beach

4.98 out of 5 average rating, 42 reviews

NEW! Waterfront Hot Tub, Heated Pool, & Golf Cart

Villa in Gulf Gate Estates

4.98 out of 5 average rating, 53 reviews

Luxury 4-Bedroom Pool Retreat Near Siesta Key

4.98 out of 5 average rating, 52 reviews

Villa in Holmes Beach

Beachfront Paradise! Ground level with Heated pool

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.

4.99 out of 5 average rating, 85 reviews

Luxury home in the heart of South Tampa & POOL!

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.

4.9 out of 5 average rating, 60 reviews

Coastal Villa w/ Amazing Courtyard - Splash Pad!

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, 57 reviews

Serene Heated Pool Oasis Tampa Vacation

4.98 out of 5 average rating, 59 reviews

A heated pool and spa are illuminated by warm outdoor string lights in the evening. The pool area features a red umbrella-covered table and chairs, along with lounge seating arranged on a brick patio surrounded by greenery.

Villa in Davis Islands

Mediterranean Villa w/ Beautiful Heated Pool/Spa

4.94 out of 5 average rating, 49 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 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!

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.

4.75 out of 5 average rating, 119 reviews

5 min to Siesta Key, Heated Pool, BBQ, Fast WiFi

5 out of 5 average rating, 49 reviews

Siesta Villa

Villa in Clearwater 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.

4.98 out of 5 average rating, 46 reviews

Walk to Beach (4 min), Pool, Private Roof Deck