Family-friendly vacation rentals in Sarasota County

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.

Downtown Bungalow-Beaches, Dining, Shopping, Shows

Welcome to The Shady Place! This charming, family-friendly bungalow is a quiet, private oasis in the heart of downtown. Here, you’ll be close to all area beaches including world-famous Siesta Key-rated by Trip Advisor as the #1 beach in the US, SRQ airport, golf courses, Legacy Trail, UTC mall, Mote Aquarium, Bayfront Marina, The Bay park, St. Armands Circle, Robarts Arena, Ed Smith Stadium-spring training home of the Baltimore Orioles, & Downtown Sarasota’s restaurants, activities & nightlife.

3 bedroom Heated salt water pool close to Siesta

Your family will be close to everything when you stay at this centrally-located place. 15 minutes to Siesta Beach, 10 minutes to UTC mall, 15minutes to downtown, 20 minutes to SRQ airport. This home is fully remodeled, fully furnished, sleeps 8. We have 1 king size bed in the master, second bedroom is queen bed, 3rd bedroom is 1 full and 1 twin beds. This is open plan home with a big family room, 60" TV above electric fireplace, formal dining room seats 6 with the bar seats 4. Master has 55"TV

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

Heated&Renovated Pool•Beach Retreat•15m to Siesta

Stay at one of Sarasota’s top-rated Airbnbs, perfectly centered between the ever famous Siesta Key and several other stunning beaches. Lounge by the newly renovated heated pool with upscale chaise lounge chairs, lush garden views, and a stylish patio with ample seating. Inside, enjoy a modern, beach vacation themed design with an open layout, fully stocked kitchen, fast WiFi, and Smart TVs in every bedroom. Your on-site Superhost is nearby but works full time and gives total privacy.

The Blessing House- Htd Pool/Spa, Close to Beaches

Welcome to The Blessing House! This home has been beautifully renovated, designed & curated for you to be rejuvenated, relaxed & inspired during your stay. You will love the heated pool & spa, the spacious lanai with plant wall, the fresh and bright design, and the amazing location of this house. The Blessing House is only a 15 min drive to Lido Key Beach & Siesta Key Beach, tons of shops & restaurants and the lovely Arlington Park is only about a 7-10 min walk away.

Bee Keepers Cottage

Welcome to Bee Keepers Cottage! Your country in the city. New guest home, private parking (2), designer interior, new stainless kitchen, microwave, dishwasher, stove with oven. Full sized washer and dryer, great high speed internet, screened porch on its own pond. Located on a 16 acre wooded property with many bird feeders, nature wildlife photo ops abound in own your backyard. See deer, wading birds, Bald Eagles, song birds and acres of privacy.

Downtown Sarasota | Casa de Zara

Welcome to Casa de Zara! Immerse yourself in Sarasota history by staying in our quaint Adobe style home built in 1925 with a serene garden filled with plants and trees native to Florida. You will be 1 mile from Main St. and 4 miles to Lido Key. One block over you will find a fun filled park with tennis and pickle ball courts, a walking path and basketball courts. Less than a mile away is Bayfront Park which is perfect for watching sunsets!

Downtown Apartment-Pool, Gym, Cowork 31

This new construction apartment features an oversized kitchen island and a slider with views of Downtown Sarasota. Shared amenities include: a gym; sunset deck; massive roof deck with a pool; gazebo with big-screen TV, fireplace, and wet bar; a dog run; and access to the adjacent Cowork office space. Also on-site is Motoneko Cafe, a full-service coffee/ramen shop that also serves tea, espresso drinks, and snacks.

Sunny Paradise w/Pool&HotTub 5 min to Siesta Key!

Family-Friendly 3BR Home w/ Private Heated Pool, Hot Tub & Backyard– Near Siesta Key! Located just minutes from world-famous beaches, and a wide variety of dining, shopping, and entertainment options, this home is the perfect base for your Sarasota vacation. Whether you’re planning a family trip, a couples’ retreat, or a friends’ getaway, you’ll love the blend of comfort, convenience, and fun!

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. 🌴

JULY AVAIL! Sarasota #1 Luxury Villa w/PRIV BEACH!

BOOK 2025 NOW, and stay in Style magazines exclusive beachfront gem! This property OWNS THE BEACH!! UNIQUE PRIVATE POOL & BEACH combo is HEAVEN! Private ELEVATOR! 32,000/gl FREEFORM POOL, with 4 WATERFALLS, HOT GROTTO with HOT falls! NEW BBQ PIT AREA, BIKES, KAYAKS, and PADDLEBOARDS! WRAPAROUND BALCONY, CHEF kitchen. Hosted CELEBS! SHOPPING, FINE DINING, watch our VIDEOS!