Villa holiday rentals in Longboat Key

4.92 out of 5 average rating, 161 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

NOV 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, 130 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, 210 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

5 out of 5 average rating, 143 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, 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, 146 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, 294 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, 116 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!

4.9 out of 5 average rating, 117 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

4.83 out of 5 average rating, 132 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

Tampa heat pool /hot tub lake view 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.

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, 173 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, 27 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!

Popular amenities for villa rentals in Longboat Key

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Private villa rentals

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)

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

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!

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.

5 out of 5 average rating, 44 reviews

Siesta Villa

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

Luxury villa rentals

4.98 out of 5 average rating, 55 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

4.98 out of 5 average rating, 47 reviews

Luxury 4-Bedroom Pool Retreat Near Siesta Key

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

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, 41 reviews

4 min Walk to Beach, Pool, Roof Deck

4.95 out of 5 average rating, 66 reviews

A heated pool is surrounded by comfortable loungers and shaded by a stylish cabana. A spacious patio area features outdoor seating, while lush greenery and tall trees create a serene backdrop under the clear blue sky.

Villa in Seminole

5 BR Luxury Beach Villa: Heated Pool & Games Room

Villa rentals with a pool

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

5 out of 5 average rating, 16 reviews

Villa in Siesta Key

The Beachwood Hideout | SK Collection

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.

4.97 out of 5 average rating, 38 reviews

Vacation Villa/Resort Pool 4 miles to Siesta Key

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

Villa in Bradenton

4.85 out of 5 average rating, 41 reviews

Heated Pool & Spa • Outdoor Kitchen/Theater/Games

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.

4.73 out of 5 average rating, 11 reviews

Charming 2/2 Village des Pins close to Siesta Key

4.78 out of 5 average rating, 172 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

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.