Vacation rentals with a pool in Fruitville

Sunshine House, close to Downtown

Great location! This is a family friendly home, close to downtown and beaches, with a pool, fenced yard, and a large, screened porch for lounging and having meals outside. Close to all the great things Sarasota has to offer- museums, gardens, theaters, shopping, Sarasota Bay, and beaches. The house is 1.5 miles from downtown, 10 min to St. Armands, 15 min to Lido Beach, and about 20 min Siesta Key Beach. One dog considered with a fee. Children must be supervised at all times in the pool area.

Heated 3BR Pool Home Glen Oaks | Close to Downtown

Family-friendly pool home near Bobby Jones Golf Club, perfectly located in the heart of Sarasota. You’re less than 10 minutes from top attractions, dining, and shopping, Downton Sarasota and just a short drive to the world-famous Siesta Beach or Lido Beach. This private home features its own entrance, a heated pool, and a fully fenced backyard—ideal for families and added privacy. We’re pet-friendly too! Comfortable, central, and close to everything—perfect for your Sarasota getaway VR24-00164

Luxury Pool Family Paradise-Siesta Beach/DT-3BR/2B

Embrace the height of comfort and convenience at your home away from home! Step into this meticulously renovated pool home, where spaciousness and brightness create an atmosphere of sheer luxury. Tucked away on a serene street, it offers a serene setting while keeping you close to Sarasota's prime attractions. Experience the allure of Siesta, the vibrant DT ambiance, and the Fresh Fish Waltz —all just moments away. Plus, enjoy easy access to I-75, Nathan Benderson Lake Park, and the new UTC.

Pool & fenced-in yard in downtown edge bungalow

MESSAGE ME FOR DAYS YOU DONT C. This 2 bed-2 bath house is a homey Florida bungalow with wood floors & natural light in a quiet neighborhood on the downtown core edge. Spacious and private fenced-in backyard with pool, covered grill and eating area. Minutes away from the Legacy Trail, the Bay Park, Payne Park, dining, live music, bars, theatres, comedy, opera house, performance venues, comedy club, antiquing, kayak launches, tennis and basketball courts, farmer's market, shopping and more.

The Oasis

Welcome to The Oasis, your Florida home away from home! Centrally located, between siesta key and st Armand’s circle, near many fantastic restaurants, grocery stores, and downtown. This home has everything you need for a fantastic stress free stay in Sarasota. A luxurious Italian style pool and garden area, a spacious indoor area with a full sized kitchen, king bed, queen bed, 1 twin bed and 2 twin air mattress. 4 smart tvs. We love this stunning and cozy home and we’re sure you will too!

Retro Beach House w/ Pool Walkable to downtown SRQ

Welcome to The "Retro Ringling", a unique designer heated salt water pool home in downtown Sarasota w/ tons of amenities and nostalgic charm- all within a stone’s throw from Main St, Payne Park, Legacy Trail & just a few short miles to the white sands of Siesta and Lido Beaches. This house provides comfortable sleeping for groups of up to 8 people (6 is ideal) & offers a private, fully fenced yard, outdoor kitchen, putting area, indoor & outdoor dining, & 4 Smart Tvs w/ high speed internet

Your private retreat near Siesta Key Beach.

Completely Remodeled Private Retreat. COME RELAX, UNWIND, AND MAKE LASTING MEMORIES! From the moment you arrive, you’ll feel the calm, welcoming atmosphere that makes this property stand out. This spacious 3brm 2-bath features an amazing heated pool, a private backyard, and stylish finishes throughout. Whether you’re lounging by the heated pool, enjoying meals in the bright open-concept living space, or exploring the nearby beaches this home is perfect for an unforgettable vacation

Pink Flamingo: 4 Beds/3 Baths Screened Pool Oasis

This wonderful pool home is located in the heart of Sarasota and just minutes away from the world-famous Siesta Key Beach! This fantastic vacation home offers 4 relaxing bedrooms and 3 full baths - there is also a Queen-size pull out sofa in the living room. A real bonus is having two master suites! The first offers a King-size bed with an adjoining bathroom featuring a walk-in shower plus his & her sinks. The second master is appointed with a Queen-sized bed and adjoining bathroom.

Sunshine Manor | Saltwater Pool + Electric Bikes!

BNB Breeze Presents: Sunshine Manor! Discover the magic of this wonderful beach home nestled in the sought-after community of Pinecraft, just 15 minutes from Siesta Key Beach! With a private flowing saltwater pool and INCREDIBLE patio space. Fully loaded home: - Heated Saltwater Pool - heated at NO extra cost from Nov 21 - April 1st - 2 Electric Bikes - Screened-In Porch w/ Seating - Fenced-In Backyard - Open Floor Plan w/ Beautiful Boho Design - Outdoor Dining Area w/ Grill

Sunshine House- Sarasota Pool Retreat

Welcome to the Sunshine House a sunny Sarasota retreat! This charming 3-bedroom, 2-bathroom home features a salt water heated pool and is just 20 minutes from the stunning Lido and Siesta Key Beaches. Perfect for families or groups, our home offers a spacious living area, fully equipped kitchen, comfortable bedrooms and an office setup. Relax by the pool, enjoy nearby dining and shopping, or explore the beautiful beaches. Your perfect getaway awaits!

Pool & Spa Oasis • Tiki Hut • 10 Min to Siesta Key

🌴 Heated Pool • Spa • Tiki Hut • 10 Min to Siesta Key Private pool oasis just minutes from Siesta Key — designed for relaxing days and unforgettable nights. Enjoy a heated pool, spa with waterfall, tiki hut lounge, and a fully screened lanai for indoor-outdoor living. Relax poolside, play outdoor games, and unwind under ambient evening lighting. Perfect for families, couples, and groups seeking a memorable Florida getaway.

Your DreamOasisAwaits: SiestaKeyEscape with Pool!

Welcome to your dream oasis near the world-famous Siesta Key! ✨ This immaculate 2BD/2BA home is a true coastal gem, offering a serene retreat with stylish design and luxurious amenities. Just 1 mile from the sugar-white sands of Siesta Key Beach, this home provides the perfect blend of comfort and convenience—an ideal spot to embrace relaxed Florida living at its finest. 🌴