Villa holiday rentals in Longboat Key

4.85 out of 5 average rating, 150 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!

4.95 out of 5 average rating, 146 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!!

5 out of 5 average rating, 153 reviews

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

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.

4.9 out of 5 average rating, 232 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!

4.9 out of 5 average rating, 172 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, 165 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, 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, 129 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

4.92 out of 5 average rating, 161 reviews

Beach so close! 1 house to beach Peaceful area

BEACH ACCESS IS STEPS FROM YOUR DOOR! A 30 second walk. 1 of 3 units in a private beachside villa tucked away on a peaceful street. A hidden gem away from busy condos. Wide beautiful beach goes for miles. Walk to many restaurants. Washer/dryer in unit. *Private patio. *Full sized kitchen. *Quiet ductless AC, *Free parking in front. *BEACH supplies provided. 1 bedroom super comfy queen bed, separate living room very comfortable pop-up sofa. 2 more units available; 1 bdm & 3 bdm.

4.91 out of 5 average rating, 130 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

4.91 out of 5 average rating, 141 reviews

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.

Villa in Tampa

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.

4.83 out of 5 average rating, 150 reviews

An outdoor space features a sparkling swimming pool surrounded by a screened enclosure. A hot tub is adjacent to the pool under warm string lights. Various games are available, including a ping pong table and a billiard table, providing entertainment options for guests.

Villa in Brandon

Resort pool/ home hot tub game room near airport

Welcome to home away from home! This beautiful 4 bedroom 2 bathroom house is new with modern decor and has everything you need for a comfortable and relaxing stay. The house features a sparkling swimming pool and a hot spa, perfect for unwinding after a long day. Located in brandon, you’ll be just 15 minutes away from downtown, where you can experience the city’s vibrant culture and attractions. Get ready to create some unforgettable memories in this charming abode.

Popular amenities for Longboat Key villa rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Private villa rentals

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

4.93 out of 5 average rating, 59 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

4.78 out of 5 average rating, 58 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!

4.97 out of 5 average rating, 90 reviews

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.

Villa in Tampa

Luxury home in the heart of South Tampa & POOL!

4.83 out of 5 average rating, 6 reviews

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.

Villa in Holmes Beach

Palm Haven Beach Side Villa

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.

4.89 out of 5 average rating, 45 reviews

Robinhood Beach Villa near Siesta Key Beach!

5 out of 5 average rating, 51 reviews

Siesta Villa

5 out of 5 average rating, 46 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

Luxury villa rentals

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

Summer Getaway with Pool and Spa

5 out of 5 average rating, 20 reviews

Villa in Venice

Florida Serene Luxury Retreat | Pool & Spa Oasis

4.98 out of 5 average rating, 61 reviews

Luxury 4-Bedroom Pool Retreat Near Siesta Key

4.98 out of 5 average rating, 65 reviews

Villa in Holmes Beach

Beachfront Paradise! Ground level with Heated pool

4.77 out of 5 average rating, 31 reviews

The exterior of The Belleair Estate is showcased from an aerial view, featuring lush landscaping surrounding the home. A private pool glistens alongside the water, with the expansive lawn leading to a private boat dock, creating a serene waterfront setting.

Villa in Clearwater

The Belleair Estate | Waterfront & Heated Pool

5 out of 5 average rating, 27 reviews

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.

Villa in Holmes Beach

Seaside Inn a waterfront in Paradise

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, 49 reviews

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

4.91 out of 5 average rating, 121 reviews

A charming gazebo is positioned beside a serene pool, surrounded by vibrant greenery. The calm waters of Lake Seminole reflect the pastel colors of the sunset sky, while the gazebo offers shaded seating for relaxation.

Villa in Largo

Waterfront Heated Pool, Sleeps 20 - 4plex

Villa rentals with a pool

4.86 out of 5 average rating, 63 reviews

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.

Villa in Tampa

Serene Heated Pool Oasis Tampa Vacation

4.97 out of 5 average rating, 37 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

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

4.94 out of 5 average rating, 53 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!

4.94 out of 5 average rating, 93 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

4.67 out of 5 average rating, 3 reviews

Villa in Bradenton

Villa Summerwind 3bed/2bath pool villa

A single-story villa is framed by landscaped greenery, featuring shrubs and palms. The exterior showcases a tile roof and light-colored walls, with windows allowing for natural light. A paved driveway is visible, leading to the entrance.