House holiday rentals in Pinecraft

4.93 out of 5 average rating, 101 reviews

[The Bay St. Hideaway]Private Swimming Pool& Patio

Welcome to Bay Street Hideaway VR24-00156 A beautiful home to make your next family vacation the best one yet! The whole group will enjoy easy access to everything from this centrally located place. The patio fenced in backyard with a private HEATED pool provides a quiet and peaceful area if you want to avoid the crowds.The house is a 2 story completely furnished with 4 bedrooms and 3.5 bathrooms. TV's are provided in the living room, a few bedrooms, and lounge area upstairs. 3 E-bikes included

A heated saltwater pool is framed by a privacy fence, with lounge chairs positioned nearby. Lush palm trees add greenery to the space, creating an area for relaxation. The clear water reflects the sky, enhancing the tranquil ambiance of the outdoor setting.

4.86 out of 5 average rating, 204 reviews

~Flamingo House~heated private pool~

Welcome to The Flamingo House! Settle in and enjoy the beautiful private pool area surrounded by privacy fence and palms, totally secluded. Take a short drive to beautiful Downtown Sarasota or Marina Jack for the sunset. Plus Legacy Trail is accessible from our street (a highlight for hikers or bikers)w/Pompano Pickleball court close by. This home is situated on a quiet street while still being close to main roads, and an easy 20 minutes to Siesta Key and Lido Key beaches,5 minutes to Pinecraft.

4.91 out of 5 average rating, 121 reviews

Coastal Farmhouse - 3/2 with heated saltwater pool

Experience relaxation at this tranquil 3BD/2BA home with a heated pool, perfect for a family retreat! Prepare meals in the fully equipped kitchen or savor local delights on the screened-in lanai. Each bedroom boasts plush bedding, ensuring a restful night's sleep. Plus, a cozy living room. Conveniently located, just under 9 miles from Siesta & Lido Key Beach, Der Dutchman 2.2 miles and 2.5 miles from Yoder's Restaurant. Shopping and dining options at University Town Center, only 7.7 miles away.

A welcoming entryway showcases a simple wooden console table with small potted plants. Above, a serene painting depicting a boat complements the neutral wall. The view to the right reveals a sun room filled with natural light, providing a connection to the private backyard.

4.95 out of 5 average rating, 182 reviews

Updated Ranch Near Beaches/Downtown - Pet Friendly

Updated cozy home with all new furnishings and appliances. 2 bedrooms 1 bathroom with an eat-in kitchen, sun room, and comfy living room. Stream shows or work virtually with our high-speed Wi-Fi. Grab the provided beach chairs, umbrella, and cooler to enjoy Lido or Siesta Key Beaches, both within a short drive. Wind down & grab drinks/dinner in downtown Sarasota or relax in the fully fenced private backyard. Enjoy several nearby golf courses, or catch Orioles spring training at Ed Smith Stadium

4.97 out of 5 average rating, 149 reviews

A single-story home is set on a corner lot, featuring a large, mature tree with lush green foliage. The property includes a light-colored exterior, a well-maintained lawn, and a gravel driveway leading to a garage. A wooden fence encloses the backyard, providing privacy.

Home in Arlington Park

Ruby's Place - Close to Beach, Downtown, Pinecraft

Ruby's Place is only 6.7 miles from the white sands of Siesta Key Beach, 5.7 miles to Lido Key and St Armand's Circle. 1/2 mile from Pinecraft and 1/2 mile from the New Legacy Trail for biking and walking. 2 Miles from Downtown Sarasota. Enjoy the beaches, explore downtown Sarasota, Kayak through the mangroves, or go see the alligators at Myakka State Park. Pompano Park Pickleball is only 5 minutes away Our house is on The corner of a popular Street in Sarasota and on a no-through street.

4.96 out of 5 average rating, 24 reviews

The Gerhardt Place (swim spa)

Welcome to The Gerhardt Place, a newly remodeled home, nestled in a quiet neighborhood right along the Philippe Creek. In this home, you will find a fully stocked kitchen, a lovely sectional couch in the living room, 4 bedrooms and 2 bathrooms, and an outdoor kitchen, perfect to cook your meals! The outdoor area in the back is fenced off. There is a roof and couch area along with a swim spa and table and chairs for you to enjoy to eat those splendid meals that you make on the grill!

4.95 out of 5 average rating, 191 reviews

Home in Bellevue Terrace

Modern 4BR Home *Heated Pool & Spa*

Discover elegance in this centrally located Sarasota gem, featuring four bedrooms and two bathrooms to accommodate up to eight guests. Enjoy a laid-back vibe while lounging at Sarasota's beaches or immersing yourself in local attractions. Siesta Beach and Lido Beach are within easy reach at 7.6 and 6.4 miles respectively. Rest easy knowing commitment to cleanliness aligns with your travel priorities. Your serene vacation awaits in this beautifully adorned home. VR24-00265

4.95 out of 5 average rating, 125 reviews

Luxury Home Near Downtown & Siesta Key Beach

Escape to this serene and spacious 3BR/2BA house on a peaceful, traffic-free street. With its high-beamed ceilings and charming details, this property exudes luxury and comfort. Discover the nearby attractions, with Siesta Key Beach just 7 miles away, Lido Beach only 6 miles away, and Downtown a mere 2.5 miles away. Start your day on the lanai with the cup of coffee before heading out to explore the shops and restaurants located just a 7-minute drive from the property.

5 out of 5 average rating, 7 reviews

Retro | Mid-Century - Pickleball, Stock Tank Pool

Retro vibes meet Florida fun in this spacious Sarasota getaway! This home features stylish vintage décor, a comfortable living space, and a huge private backyard built for play. Enjoy the pickleball court, basketball hoop, mini golf, heated or chilled stock tank pool, outdoor kitchen, huge, covered lanai and bed swing. Perfect for families or groups looking to relax, play, and make unforgettable memories just minutes from Sarasota’s beaches, downtown, and attractions.

A modern two-story home is featured, showcasing a combination of light-colored exterior panels and stone accents. Lush tropical landscaping surrounds the property, with manicured shrubs and decorative plants lining the driveway, which is paved with stones.

4.95 out of 5 average rating, 104 reviews

Linda's Place

Come enjoy our family's brand-new, meticulously manicured home in Pinecraft! Located on a quiet, dead-end street, but just minutes from all Sarasota has to offer. With 5 bedrooms -each being a suite with a private bathroom- and a sprawling, open floor plan, our home is ideal for larger families or groups. The screened-in, heated, pool in the private backyard surrounded by lush landscaping provides a quiet place to relax and make memories! Minutes away from the beach!

Superhost

4.77 out of 5 average rating, 128 reviews

4bd/3bth Renovated With Heated Pool near Downtown

Located in one of Sarasota’s most sought-after central neighborhood. Enjoy a short drive to the Downtown Sarasota Farmers Market, local art festivals, theaters, and vibrant dining. You’re just minutes from St. Armands Circle, and the award-winning beaches of Siesta Key, Lido Key, and Longboat Key. The nearby Legacy Trail —perfect for walking, biking, running, or rollerblading while enjoying Florida’s natural beauty and Sarasota’s rich history. CERT #VR24-00203

A charming cottage exterior is surrounded by lush landscaping, featuring vibrant flowering plants and manicured greenery. The front porch is accessed by a walkway, with a welcoming entrance illuminated by natural light. The garage door adds functional design to the home.