Villa holiday rentals in Longboat Key

Starfish House - 2bed/2bad

An Anna Maria Island Vacation to remember is waiting for you at Starfish Beach #4. This charming complex is small and quiet, perfect for a relaxing beach getaway. A shared pool is available in the courtyard. You'll enjoy being just steps from the Anna Maria Public beach access. With a short walk, finding your place in the sand each morning will be easier than ever! 50 yards to the BEACH! Bed size: 1 K, 1 Q, sleeper Baby accessories available for rent. Snoo Bassinet high chair pack and play

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! Cute Lux Beach Villa, 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!

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.

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.

Heated Pool+Fire Pit+Trails+4 min to Beach

A newly updated modern beach house with a resort style backyard including a HEATED pool, fire pit, outdoor TV with comfortable sectional and an eating area, grill, lounge chairs, corn hole, pool volleyball and much more! All this and it is located just 4 minutes to Indian Shores Beach, and 20 minutes north along the beach is the world famous Clearwater Beach. This house is centrally located with John's Pass only 12 mins away. Downtown Gulfport and St Pete Beach are all 25 mins away.

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

Dolphin Cove Waterfront St. Pete Beach w/ Pool

THIS is the Florida life! A private oasis with a stunning tropical backyard and an oversized SALTWATER pool. Enjoy 140+ ft of waterfront on Bear Creek canal, where manatees and dolphins visit daily! Kayak just 15 minutes to nearby islands. Beaches are a quick 7-minute drive, downtown is 15 minutes away, and shops/restaurants are right across the street. The home is simple and unupdated, but the backyard is a true paradise you won’t forget!

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

Almost beachfront! 1 house to beach. 2 King 2 twin

Just a 1-minute walk to a gorgeous Gulf beach with breathtaking sunsets and miles of white sand! Walk to restaurants, then relax in this peaceful, hidden gem tucked away from busy condo crowds. One of only 3 units in a charming Gulf-side villa. Includes beach chairs, towels, cooler, washer/dryer, Wi-Fi, free parking, central A/C, and nearby pickleball. Sleeps 6 with 2 king bedrooms and 1 bedroom with 2 twins.

Couples retreat•5 Min Walk Beach. Endless Sunsets

Fall in love with Flipper’s at Mad Beach, a private, newly renovated coastal oasis designed for romantic getaways. Located just a few steps from the sugary sands of Madeira Beach, this intimate retreat offers the perfect blend of modern luxury and relaxed beach vibes. It is the ultimate hidden gem for couples seeking a peaceful, private, and memorable vacation by the ocean.