
Villa holiday rentals in Longboat Key
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Top-rated villa rentals in Longboat Key
Guests agree: these villas are highly rated for location, cleanliness and more.

The Palm Haus • Heated Pool • Near Beach • Games
Charming home with stylish baths & bedrooms. Heated pool included in the price. Gas fire-pit, outdoor games, large secluded backyard! Game room! Near Honeymoon Beach & Caladesi Island open for sunbathing & water sports; historic downtown Dunedin with cute shops, cafes, restaurants & cultural events. The area has a number of top-notch golf courses and trails. Palm Harbor's welcoming community & mild climate make it an ideal getaway for outdoor adventures, cultural experiences, and coastal views.

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!

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!!

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.

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!

Beach soo close! 1 house to beach Peaceful Cozy
1 HOUSE TO BEACH! 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. Pickle ball courts nearby! **Washer/dryer in unit. *Private patio. *Full sized kitchen. *Quiet ductless AC, *Free parking in front. *BEACH supplies-cooler, chairs, towels 1 bedroom super comfy queen bed, separate living room comfy pop-up sofa. 2 more units available; 1 bdm & 3 bdm.

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.

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

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

The Emerald Villa, Eco-Luxury by the Sea
Eco-friendly, earth conscious seaside villa. Located just steps from the soft sands of the Gulf of Mexico beach, this exquisitely designed family home offers a luxurious yet sustainable escape. Encased in natural light, 4 bedrooms and 3 baths, the villa sleeps dynamic families and small groups in uncompromising comfort and style and provides all the zen essentials. In-house health suite with gym, infrared sauna and red light therapy available upon request at small additional daily fee.

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.

Waterfront saltwater Pool home w boat slip
2 King Beds 1 bath Vintage cottage w outdoor saltwater pool on intracoastal waterway. Perfect for 1-4 guests. Bring your small boat no charge. ( Must provide your own supplies/ ties/ bumpers) Great for water sports, fishing, nature lovers. Only quiet respectful guests welcome. Work from home office with a beautiful view. This is someone's private home half of the year. It's professionally cleaned, welcoming, down to earth. BTR1587
Popular amenities for villa rentals in Longboat Key
Private villa rentals

IRB Harbor House Semiprivate Waterfront Pool Villa

Lilo & Stitch Ohana Villa|Heated Pool Near AMI

Waterfront Condo, Close to Beach, with Boat Dock!

The Tropical Oasis, w/ Solar Heated Pool and Games

Seaside Inn a waterfront in Paradise

the Seaside 21

Starfish House - 2bed/2bad

Siesta Key*PRIVATE BEACH*Gulf Side*Heated Pool
Luxury villa rentals

Private Beach Villa | Charming Decor | Sunset View

Summer Getaway with Pool and Spa

Luxury 4-Bedroom Pool Retreat Near Siesta Key

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

Bohemian Inspired Villa with Golf Cart and SUV

NEW!~ Beach Front/Heated Pool! Coconuts 107

Waterfront Heated Pool, Sleeps 22 - 4plex

Luxury Villa w/ Private Pool
Villa rentals with a pool

Paradise Villa- Sarasota

Gorgeous Villa with Heated Pool & Beach Views!

Villa Perdomo Family

Modern Luxury Villa - Heated Pool Spa, Game Room

Coastal Cottage | Top 1% Airbnb Worldwide

7891 Timberwood, Sarasota, Florida, USA

Busch Gardens Deluxe Edition w/heatedpool

Fully renovated villa on Siesta Key
Quick stats about villa rentals in Longboat Key

Total holiday rentals
Explore 10 holiday rentals in Longboat Key

Nightly prices starting at
Longboat Key holiday rentals start at €95 per night before taxes and fees

Verified guest reviews
Over 350 verified reviews to help you choose

Family-friendly holiday rentals
10 properties offer extra space & child-friendly amenities

Wifi availability
10 of Longboat Key holiday rentals include wifi access

Popular amenities for guests
Guests love Kitchen, Wifi and Pool across Longboat Key rentals

4.8 Average rating
Longboat Key stays are highly rated by guests – averaging 4.8 out of 5!
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