Villa holiday rentals in Longboat Key

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 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!

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!

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!

Villa at Harbor House "Villas by Christine"

Welcome to The Villa at Harbor House, located just steps from Safety Harbor’s Main Street, ranked the #10 Main Street by USA Today in 2025. Enjoy convenient walkable access to charming shops, dining, and pubs. This villa is perfect for solo travelers or couples, offering a queen bedroom, fully stocked kitchen, spacious living room, smart TVs, full laundry, and more. Pet-friendly ($100 fee). Beach gear included. For larger groups, consider booking Villa Key West or Villa Italia, steps away.

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

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.

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

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

Water Front Villa 1; 5 min walk to beach & dinning

Beautiful Clearwater Beach, 2 bedroom villa direct waterfront located on the Mandalay Channel. WE feature 2 queen bed units with full kitchen and dining area as well as a beautiful waterfront view from the nicely appointed living room. Check out all our 5 STAR reviews and you will want to stay here too !! Very short 2 min walk to Clearwater Beach. We now have washer and dryer on site for guest use, no fee.