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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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A welcoming living room is highlighted by a cozy yellow sofa, a hanging egg chair, and a round coffee table. Light streams through a large window, illuminating decorative plants and a vibrant area rug, while playful wall art adds a touch of charm.

4.89 out of 5 average rating, 108 reviews

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

New Solar Pool Heater just installed! Prime location, 5-9 mins drive to Indian Rocks Beach, Belleair Beach, Florida Botanical Garden, Splash Harbor Water Park, restaurants, groceries, shops. 15-20 mins drive to Clearwater Beach, Madeira Beach. Super cute, renovated, spacious, and well-stocked vacation house, featuring a dreamy pool/lanai, tropical decors, and plenty of entertainment (games, 3 Roku TVs 43'-58', beach amenities). 4 queen/full beds & all new furniture. Perfect family getaway!

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, 160 reviews

JULY SALE! Beach 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 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

4.86 out of 5 average rating, 118 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!

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

4.95 out of 5 average rating, 113 reviews

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!!

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

4.89 out of 5 average rating, 208 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!

Top guest favorite

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.

4.97 out of 5 average rating, 135 reviews

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.

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.

4.9 out of 5 average rating, 112 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.

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

4.81 out of 5 average rating, 114 reviews

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.

Villa in Drew Park

4.88 out of 5 average rating, 155 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.

Top guest favorite

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

5 out of 5 average rating, 107 reviews

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.

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, 105 reviews

Florida Living

This House has 3 bedrooms, 2 bathrooms, kitchen, living & dining, Pool, GAME ROOM (Pool Table, Fossball ,Bar ) 65 inchTV, wireless internet. It is conveniently located near local attractions, yet secluded and quiet. If you are looking for a private escape in a peaceful setting with comfortable furnishings and a lot of fun games this property is for you and your family .

Top guest favorite

A welcoming entrance is framed by lush greenery, featuring a gravel driveway leading to a modern one-story house. Large wooden doors provide access, while well-maintained landscaping adds to the inviting atmosphere.

Villa in Sarasota

4.94 out of 5 average rating, 52 reviews

Beautiful House w/ Pool, 10 Min to Siesta Beach

Take it easy at this unique and tranquil getaway. This completely remodeled 2 bedroom pool house is a stylish modern haven that's sure to delight. The striking façade and enviable location will instantly leave you in awe. Set on a long tree-lined drive with impeccable water views. Take a dip in your shimmering swimming pool or gather around the fire pit.

Vacation rentals for every style

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Quaint homes, peaceful surroundings

Popular amenities for Longboat Key villa rentals

Free parking on premises

Air conditioning

Private villa rentals

A spacious balcony showcases comfortable seating with colorful Adirondack chairs in red and yellow. The railing offers an unobstructed view of the surrounding area and the water. A bright sky with scattered clouds enhances the inviting outdoor space.

Villa in Bradenton Beach

4.8 out of 5 average rating, 30 reviews

Booking for Summer! Short walk to the beach-Unit A

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

4.9 out of 5 average rating, 20 reviews

Northshore BeachHouse West Anna Maria Island

A bright kitchen features a cheerful, colorful wallpaper with a playful design. A traditional farmhouse sink is situated on a light blue countertop, accompanied by various kitchen utensils and knives mounted on the wall. A vibrant yellow door complements the lively aesthetic, inviting natural light.

Villa in Gulfport

4.88 out of 5 average rating, 84 reviews

Cozy funky duplex with KING bed

A sparkling pool is featured within a screened-in area, surrounded by brick pavers. Comfortable lounge chairs are positioned beside the water, while a dining table with chairs is visible in the shaded area. Lush greenery is present in the background, enhancing the outdoor setting.

Villa in Bradenton

5 out of 5 average rating, 4 reviews

Florida Villa Sunrise - 4 Bedroom Home with Pool

A single-story home is set amidst lush landscaping and palm trees. The exterior features a light green color with a covered front porch. A stone-paved driveway leads to the entrance, surrounded by neatly arranged white gravel and vibrant greenery.

Villa in Sarasota

4.93 out of 5 average rating, 54 reviews

Palm Paradise: Near Beach, Heated Salt Water Pool

Top guest favorite

A modern living space is visible, featuring a spacious gray sofa facing a flat-screen television on an elegant media console. A wooden dining table with high-backed chairs is positioned near a well-equipped kitchen displaying stainless steel appliances and warm wood cabinetry. Natural light brightens the area.

4.97 out of 5 average rating, 130 reviews

A Wave From It All Villa W King Beds

A modern kitchen features sleek cabinetry, stainless steel appliances, and a central island with seating. Light-colored countertops and wood grain flooring create a bright and inviting space. Natural light is provided by a window, while an open layout connects the kitchen to the living area.

Villa in Sarasota

4.83 out of 5 average rating, 53 reviews

Your own tropical paradise in Sarasota

Top guest favorite

The image showcases a large swimming pool surrounded by a paved patio, featuring multiple lounge chairs positioned along its perimeter. Umbrellas provide shade while trees and green foliage create a natural backdrop under a clear blue sky.

Villa in Sarasota

5 out of 5 average rating, 30 reviews

NEW-Cheerful 2-bedroom villa-13 min. to Siesta Key

Luxury villa rentals

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 Pass-a-Grille Beach

5 out of 5 average rating, 3 reviews

Private Beach Villa | Charming Decor | Sunset View

An inviting outdoor space features a sparkling pool surrounded by patio furniture, ideal for relaxation. The property includes well-maintained gardens and a charming exterior of the villa, showcasing its spacious layout and resort-like atmosphere. Multiple living areas add to the comfort of the home.

Villa in Sarasota

4.97 out of 5 average rating, 38 reviews

Luxurious 4-Bedroom Retreat with Pool

A spacious outdoor area features a heated pool, surrounded by lounge chairs and tropical plants. A covered patio is seen nearby, with seating and a BBQ grill for outdoor gatherings. The pool glimmers under natural light, inviting relaxation.

4.97 out of 5 average rating, 30 reviews

(HGR) Heated pool villa. Boat rental available

Top guest favorite

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, 75 reviews

Luxury home in the heart of South Tampa & POOL!

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

4.97 out of 5 average rating, 33 reviews

4 min Walk to Beach, Pool, Hot Tub, Roof Deck

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

4.97 out of 5 average rating, 60 reviews

5 BR Luxury Beach Villa: Heated Pool & Games Room

A private heated pool is surrounded by palm trees and a meticulously paved patio. The three-story home features a covered seating area with gray outdoor furniture and a staircase leading to the upper levels. Light filters in from large windows, enhancing the inviting outdoor space.

Villa in Holmes Beach

5 out of 5 average rating, 3 reviews

La Isla Bonita by Coastal Chic Vacations

A private outdoor pool surrounded by lush greenery is featured, with a gazebo in the background. Lounge chairs are positioned nearby, and colorful pool floats are scattered on the water's surface. The space is brightened by blue skies and white fluffy clouds.

4.97 out of 5 average rating, 94 reviews

Waterfront Heated Pool, Sleeps 20 - 4plex

Villa rentals with a pool

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

4.92 out of 5 average rating, 39 reviews

Villa Luxe~Heated Saltwater Pool~Near Beaches

Villa in Seminole

4.78 out of 5 average rating, 18 reviews

Free Beachy Vibes Home

Villa in Bayou Oaks

4.75 out of 5 average rating, 20 reviews

Tiki Bella Villa (Entire home with Pool)

A two-story home is showcased with a charming balcony and large French doors overlooking a heated pool and spa. The outdoor area features a spacious patio made of pavers, along with a seating area. Lush greenery surrounds the pool, creating a private ambiance.

Villa in Davis Islands

4.98 out of 5 average rating, 51 reviews

Mediterranean Villa w/ Beautiful Heated Pool/Spa

4.86 out of 5 average rating, 64 reviews

Best deal in town!

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.

Villa in Sarasota

4.7 out of 5 average rating, 10 reviews

Charming 2/2 Village des Pins close to Siesta Key

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, 37 reviews

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

Villa in Treasure Island

4.88 out of 5 average rating, 17 reviews

Luxury waterfront in the heart of treasure island

Quick stats about villa rentals in Longboat Key

Total rentals
10 properties
Nightly prices starting at
G$20,910 GYD before taxes and fees
Total number of reviews
320 reviews
Family-friendly rentals
10 properties are a good fit for families
Wifi availability
10 properties include access to wifi
Popular amenities
Kitchen, Wifi, and Pool

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