
Villa vacation rentals in Longboat Key
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Top-rated villa rentals in Longboat Key
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APRIL OPEN 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...:)

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!!

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!

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 - 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

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

30 sec walk to beach 2 king beds 2 twin. Superhost
30 second walk to gorgeous beach with amazing sunsets and miles of beachfront. Tucked away on a quiet street, a hidden gem away from busy condos. 1 of 3 units in a small villa on the beach side. Walk to restaurants. Bedrooms & Comfort 🛏️ 2 bedrooms with King beds, 1 bedroom with 2 Twin beds (this room has W/D). Blackout curtains & comfy mattresses for restful nights. Amenities 🏖️ Beach towels, chairs & cooler. W/D in unit, central AC, Wi-Fi, free parking in front. Beach right there!

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

A Wave From It All Villa W King Beds
Fully renovated 2 bedrooms with 2 King beds 2bath unit, has all the stainless steel appliances everything you could possibly need for your vacation time. The home is located 7min from buccaneers stadium, 5 mins from St. Joseph hospital, 10 mins to international mall, 10 mins to Soho. Home is in the heart of Tampa Bay! -Tampa International Airport 8.6MI -Tampa Bay Buccaneers Stadium 2.2MI -Aquarium7.6MI -Busch Gardens8.4MI -Clearwater24MI -Adventure Island9.0MI

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!

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.
Popular amenities for Longboat Key villa rentals
Private villa rentals

Villa Luxe~Heated Saltwater Pool~Near Beaches

Northshore BeachHouse West Anna Maria Island

Robinhood Beach Villa near Siesta Key Beach!

Newly Remodeled Luxury Beach Villa on Siesta Key!

Coastal Cottage

10 Minutes to Beaches! Mint House

River Pointe 3/2 Lakefront Home with Heated Pool

ZoriLux Villa | Pool • Billiards • Firepit • Oasis
Luxury villa rentals

Family Haven/Kid's Amenities Near Honeymoon Island

[TRENDlNG] Modern 5BR Pool Villa + Arcade & Sauna

NEW! Waterfront Hot Tub, Heated Pool, & Golf Cart

Beachfront Paradise! Ground level with Heated pool

Luxury home in the heart of South Tampa & POOL!

Villa Blanca - Waterfront Midcentury Modern Home

Paradise with a pool, pier and private beach area

Waterfront Heated Pool, Sleeps 20 - 4plex
Villa rentals with a pool

La Villa, 1 of 4 rentals on-site. Heated Pool!

Tiki Bella Villa (Entire home with Pool)

Relax just steps from beach & Gulf of America

5 min to Siesta Key, Heated Pool, BBQ, Fast WiFi

Charming 2/2 Village des Pins close to Siesta Key

Walk to Beach (4 min), Pool, Private Roof Deck

The Citrus Hideout – SK Collection

Busch Gardens Deluxe Edition w/heatedpool
Quick stats about villa rentals in Longboat Key

Total vacation rentals
Explore 10 vacation rentals in Longboat Key

Nightly prices starting at
Longboat Key vacation rentals start at ﺩ.ﺇ404 per night before taxes and fees

Verified guest reviews
Over 320 verified reviews to help you choose

Family-friendly vacation rentals
10 properties offer extra space & kid-friendly amenities

Wi-Fi availability
10 of Longboat Key vacation rentals include wi-fi 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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