
Villa holiday rentals in Little Gasparilla Island
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Top-rated villa rentals in Little Gasparilla Island
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Escape to Casa Blu- private pool, minutes to beach
Your next retreat to Florida paradise should be Casa Blu with it's private pool and serene backyard. It's just minutes to area beaches, restaurants and parks. Let the stresses of daily life melt away as you float in the salt water pool, sipping margaritas, listening to Jimmy Buffett singing "It's Five O' Clock Somewhere" The single-floor layout, comfy bedrooms with private baths await. Fast WiFi, Smart TVs, and fully equipped kitchen. Everything's covered, from beach gear to a pack 'n play.
4.93 out of 5 average rating, 148 reviews
Corallo House | Heated Pool | Free BBQ
NO SERVICE FEE WE COVER IT FOR YOU Welcome to our stunning luxury AIRBNB! We're thrilled to offer you a one-of-a-kind experience that combines elegance, comfort, and convenience. We have created this space with the utmost attention to detail, so we hope you'll appreciate the high end finishes. We've also provided a range of amenities to make your stay even more enjoyable, high-speed wifi, smart Tv's, premium bedding and toiletries. Relax with the whole family at this peaceful place to stay.
4.93 out of 5 average rating, 169 reviews
SEP SALE! Cute Sarasota 2Br/2BTH Beach Villa! Pets
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!
4.89 out of 5 average rating, 179 reviews
Pool·Game Room·Beach Gear·Spotless.5 min to Beach
<b>🏖️ Come & Enjoy FL as it should be! 🏖️ Your beach paradise awaits minutes from Englewood's Gulf Coast! 🌊 Heated Pool (FREE Nov-Apr!) 🎮 Game Room - Pool, Darts, Air Hockey 🌴 Screened Lanai & Tiki Bar 🔥 Cozy Fireplace & Reading Nook 🏄 Beach Gear Included 🍹 Blackstone Grill 📺 2 Smart TVs & High-Speed WiFi 🍳 Fully Stocked Kitchen - Spices, Pots, Pans and cutlery 🗺️ Minutes to Englewood, Manasota & Gasparilla Beaches ⭐ 4.97 Rating - Book Now !Don't miss your Gulf Coast escape! 🌅
4.97 out of 5 average rating, 118 reviews
Stunning Villa in Golfer's Paradise/Canal Views
Welcome to your new home in Rotonda West! This 3-bedroom, 2-bathroom gem on Marker Rd is all about comfort, style, and tranquility. As soon as you step inside, you'll be greeted by a spacious and open floor plan that will make you feel right at home. We're excited to share that each room in the house is equipped with a TV for your entertainment pleasure. And guess what? Two of them even have Roku TV, so you can stream all your favorite shows and movies with ease.
4.96 out of 5 average rating, 28 reviews
Stunning Bay Waterfront! Jaw dropping Water Views!
Spectacular Lemon Bay views! Upstairs at Blue Island Inn, waterfront “Bella Vista” with Bay & Pool views! 2 bedrooms; kitchenette & family room. Enjoy “Lemon Bay-front beach” in backyard. Low-key quiet vacationers. 1 car parking spot. No visitor parking. Free 2 kayaks. Login to your favorite streaming services with Smart TVs. Beautiful Blind Pass Beach, Englewood Beach, 5 restaurants & Tiki Bars are just 1.5 mile away or hop on Stumpy's Free Shuttle (tip based)
4.99 out of 5 average rating, 141 reviews
Gulf Coast Floridian Villa with Pool
Your Perfect Florida Getaway Awaits! Bring the whole family to this stylish and spacious 4-bedroom villa with a heated pool. Located in a quiet neighborhood, just a short drive from beautiful beaches, lively bars, and top restaurants. Relax with a BBQ on the patio overlooking the golf course, take a swim, or cycle the scenic Cape Haze Trail. Sunshine, space, and unforgettable memories—book your stay today! Please note that the pool is heated at no extra cost.
5.0 out of 5 average rating, 83 reviews
3's Company-'Villa Jack' **1 block to the Gulf
Manasota Key is one of the best kept secrets on the Gulf coast. "Villa Jack" is only 1 block to the Gulf and walking distance to the local restaurants and shopping. We have 2 Villas that can be rented individually or as a group. "Villa Janet" is a 1 bedroom with king bed and a pull-out couch and bath. "Villa Jack" : is a 1 bedroom-king bed, 1 bath unit. Each unit has its own private entrance and a shared area in the back with outdoor furniture and grill.
4.83 out of 5 average rating, 84 reviews
Englewood Beach Villa - 3 min Walk to the Beach!
Welcome to the Beach! Relax and unwind in your own private home! Our villa is located across the street from Englewood Beach, making it about a 3-minute walk to the Gulf sands. Nothing is overlooked for your comfort. It has two beds—a king and a queen—for a good night's sleep on comfortable recently purchased mattresses. Two full bathrooms. Swim in a heated pool, then walk to one of six restaurants for your next meal. Perfect for a fun Florida getaway!
5.0 out of 5 average rating, 18 reviews
Luxury Retreats at Boca Grande - Boca Bay Watch
Watch the yachts cruise by en route to and from Miller's Dockside, while rocking on your private and serene breeze-filled balcony. Boca Bay Watch sleeps 8 and has 3 bedrooms and 3 bathrooms. This charming villa is a quick walk or golf cart ride downtown Boca Grande for shopping and dining. It is a most idyllic and exclusive community. Very walkable area allows for viewing of local palms and birds and exotic wildlife in addition to local attractions.
4.88 out of 5 average rating, 43 reviews
"Pelican Nest" Private Beach & Bay access & Pool
"Pelican Nest" Beautiful Manasota Key Beach Villa with all the amenities; heated pool, electric fireplace, skylights, granite counters, stainless appliances. Very inviting for fun with family and friends by the beach, or in the bay. Has 4bedroom , 3 bath sleeps 10 people, with 2pull up sofas, 2full kitchen, jacuzzi .The backyard has a room for play and entertaining, BBQ. We look forward to hosting you . Max 4 car parking
4.89 out of 5 average rating, 35 reviews
Fun in the Sun
FUN IN THE SUN - Come and experience fun in the sun at our Rotonda West villa. Enjoy the outdoors indoors by opening up the great room to the patio and lanai with heated pool & spa, nestled on the Rotonda River. Enjoy the views of the sunset and wildlife in the backyard. Golf at your choice of five courses in the community. Fish off the canal bank or lounge in the sun at the Boca Grande off the Gulf.
4.98 out of 5 average rating, 50 reviewsPopular amenities for Little Gasparilla Island villa rentals
Private villa rentals

Steam Shower Heat Pool, Premium Oasis, bring pets
4.85 out of 5 average rating, 34 reviews
Sun-Kissed Villa A
5.0 out of 5 average rating, 11 reviews
Waterfront Villa - Heated Pool - Pet Friendly
4.89 out of 5 average rating, 37 reviews
Waterfront Villa with heated Pool
4.83 out of 5 average rating, 52 reviews
Canal Front 3-Bedroom Grand Villa with Pool
4.81 out of 5 average rating, 53 reviews
Spacious Duplex | Sleeps 13 | 8 Beds | Near Beach
4.93 out of 5 average rating, 15 reviews
Enjoy Sunny Waterfront Beaches, Golf/fishing Home
4.97 out of 5 average rating, 65 reviews
Beach Vibes
4.86 out of 5 average rating, 7 reviewsLuxury villa rentals

Ultimate Luxury Oasis, Pool, Perfect for Family
4.78 out of 5 average rating, 37 reviews
Waterfront Unique Euro Villa heated salt pool dock
5.0 out of 5 average rating, 5 reviews
Beautiful Villa! Private Pool Bike to Boca Grande
4.6 out of 5 average rating, 10 reviews
Luxe 5 BR/4 bath. Dock/Lift. View. Pool. Hot Tub.
4.77 out of 5 average rating, 31 reviews
New Mgmt~Tropical Indoor Pool/Hot Tub+Pool Table
4.66 out of 5 average rating, 74 reviews
Luxury 4BR Villa | Heated Pool + Fireplace
5.0 out of 5 average rating, 10 reviews
Serenity’s Edge, Pool, Views & Gulf Access

Beautiful 2BR Villa near Charlotte Harbor
Villa rentals with a pool

ENDLESS SUMMER Villa with heated salt water pool
4.82 out of 5 average rating, 65 reviews
Sanctuary w/covered heated saltwater pool on canal
4.84 out of 5 average rating, 97 reviews
Direct Gulf Front – Venice Villas Coastal Chic

Coastal Retreat Villa with pool • near beaches
4.98 out of 5 average rating, 106 reviews
Secluded Paradise,Heated Pool,Beaches and Golf n.
4.99 out of 5 average rating, 90 reviews
Lakehouse
4.98 out of 5 average rating, 55 reviews
Dolphin Oasis - Villa Close to SW Florida Beaches
4.91 out of 5 average rating, 81 reviews
Spacious Home with Heated Pool Near Beaches
4.97 out of 5 average rating, 39 reviewsDestinations to explore
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