Family-friendly vacation rentals in Sarasota County

4.91 out of 5 average rating, 123 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.

An outdoor area features a heated pool surrounded by a spacious deck. Lounge chairs are positioned nearby for relaxation, and a dining set offers seating for outdoor meals. A screened enclosure provides protection from insects while allowing natural light to filter through.

4.92 out of 5 average rating, 131 reviews

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

A charming outdoor patio features a wooden pergola draped with fabric, providing shade over a seating area with four chairs. Lush greenery, including a palm tree, surrounds the cottage, nestled on a gravel area, creating a serene and inviting atmosphere.

4.98 out of 5 average rating, 137 reviews

The Mango House Beach Cottage

Our cozy boho beach cottage, The Mango House is the perfect place for a couple or small family to relax and enjoy all the best Sarasota amenities. It’s conveniently located right between both Siesta Key entrances, walking distance to restaurants, grocery stores, Trader Joe’s, gym and a block from the popular Walt’s Fish Market. This gorgeous bungalow is the front house of a duplex on a large lot with plenty of cozy private outdoor space to relax and take in all the wonderful Florida weather!

4.88 out of 5 average rating, 265 reviews

Tiny home in Sarasota

@Tiffanythetinyhome| island | netflix|bike|hammock

You are about to book a famous HGTV 270ft² / 25m² tiny home on a private 1.5-acre island! ☆ Walk to dining, nightlife, and shopping ☆ Fully equipped kitchen (K-cup) ☆ Backyard fire pit + BBQ ☆ Screened-in outdoor lounge w/ hammocks ☆ 415Mbps ☆ Smart TV w/ Netflix ☆ Memory foam bed ☆ FREE Bikes + kayaks + beach gear 3 min → Siesta Key Beach 7 min → Downtown SRQ 12 min → Myakka River State Park (river kayaking + wildlife viewing) We use a compost toilet. Please read house rules for info.

An aerial view showcases a tranquil pool area surrounded by lush landscaping. Comfortable lounge chairs are positioned around the curved pool, accompanied by several shaded umbrellas. A covered seating area and palm trees enhance the inviting outdoor space.

4.91 out of 5 average rating, 23 reviews

Modern Escape with Pools Near Sarasota’s Best!

Modern Skye Ranch townhome perfect for tourists or families .Features 2 master suites upstairs (each with private bath) plus a half bath downstairs. Fully equipped kitchen, Wi-Fi, Smart TVs, washer/dryer & lanai. We provide full beach gear (chairs, umbrella, cooler, towels) plus bathroom essentials (shampoo, dryer, blankets). Pet-friendly! Enjoy 2 resort pools, sports courts, trails & dog park. Minutes from Siesta Key, Lido Beach & downtown Sarasota. 5-star reviews! Book your getaway today!

4.93 out of 5 average rating, 397 reviews

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.

A covered patio area features modern wicker furniture with white cushions, positioned around a glass coffee table. The inviting space overlooks a pristine pool, surrounded by a protective screen. Lush greenery is visible in the background, enhancing the tranquil setting.

4.96 out of 5 average rating, 136 reviews

Luxury Pool Family Oasis-Siesta Beach Beac-3BR/2BA

Welcome to your home away from home! This renovated, spacious and bright pool home will immerse you into a luxurious experience the minute you arrive. Located on a lush quiet street, yet close to all of Sarasota's best attractions! Close to Siesta Key Beach (#1 beach in USA), 10 minutes to downtown including fantastic restaurants and shopping and walking distance to the famous Fresh Fish Waltz Market. Easy I-75 access, Nathan Benderson Recreational Lake park and The new UTC mall!

4.95 out of 5 average rating, 192 reviews

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

A modern house is presented with a neatly manicured lawn and a driveway leading to a garage. Lush palm trees and potted plants frame the entrance, while large windows allow natural light to fill the interior. The structure has a welcoming white facade under a gray roof.

4.96 out of 5 average rating, 105 reviews

Casa Cruz-3RM/2BA w/Heated Salt Water Pool

You'll have a great time at this modern 3RM/2 BA house with a heated salt water pool. This beautiful home is located 6 minutes to SRQ Airport, 20 minutes to the #1 rated beach in the country, Siesta Key, 5 minutes to Publix and local restaurants, and 10 minutes to high-end shopping at UTC mall. You’ll have access to major FL highways. The home is equipped with all the essentials needed for short term/long term stays. Book your stay today! Casa Cruz es su Casa!

A charming 1920s cottage is set in a lush green landscape, accentuated by carefully arranged flowerbeds. The light yellow exterior is complemented by a white porch and a metal roof. The surrounding trees provide shade, creating a peaceful and inviting outdoor space.

4.97 out of 5 average rating, 133 reviews

Bright & Peaceful 1920s Cottage: Close to UTC!

Experience the timeless charm of this 1920s beautifully preserved cottage – where original details meet modern comforts. A bright & peaceful property nestled on half an acre with plenty of space to spread out, natural light that pours into every room, & a private fenced in yard - it's an ideal spot to entertain AND unwind. Whether you are headed to the beach, Benderson Park, Downtown or UTC mall, this neighborhood is central to anything you'll need!

4.98 out of 5 average rating, 116 reviews

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. 🌴