Family-friendly vacation rentals in Sarasota County

Beachy Cottage close to Siesta | 3 Bed | Huge Pool

Welcome to The Salty Unicorn, your cheerful Sarasota escape just five miles from Siesta Key Beach. This fully renovated 3-bedroom home is designed for relaxation and fun, with a bright open layout, stylish coastal décor, and plenty of space to gather with family or friends. Start your mornings with coffee by the pool, spend sunny afternoons swimming or lounging in the spacious backyard, and end the day with dinner in the screened lanai. Whether you’re here for beach days, family time, or a peace

Sun-filled cottage with pool, walk to beach

Welcome to Palm Cottage. Our space is the perfect cozy getaway for any time of year. Recently renovated three bedrooms and one bathroom make this the perfect spot for two couples or a family. The private backyard includes a brand new pool with a hot tub and a sun shelf, as well as outdoor dining area and fire table. Enjoy a leisurely stroll to Siesta Key to play at the beach or grab a meal at one of the many restaurants. Home includes two bikes and all the gear you need for a day at the beach.

Sunshine House, near Downtown, Legacy Trail, Beach

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.

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!

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. *Brand new pool* VR24-00265

@Shellmateisland |tiny home| island| bikes| kayaks

⭑Octagonal 320ft² tiny home sitting on a private 1.5-acre island!⭑ ✯ Lake access ✯ Walk to dining, nightlife, and shopping ✯ Fully equipped + stocked kitchen ✯ Free bikes + kayaks +beach gear ✯ Backyard fire pit + BBQ ✯ Screened-in outdoor lounge w/ hammocks ✯ Smart TV w/ Netflix ✯ Memory foam bed ✯ 426Mbps wifi Ask which fruit trees are in season for a homegrown treat! 3 min → Siesta Key Beach 7 min → Downtown SRQ 12 min → Myakka River State Park (river kayaking + wildlife viewing)

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

Welcome to The Blessing House, a beautifully curated Sarasota retreat designed for relaxation, comfort, inspiration, and quality time together. Enjoy a heated pool & spa, lush lanai, bright designer interiors, and a peaceful residential setting just 15 minutes from Siesta Key, Lido Key, and downtown Sarasota. Thoughtfully maintained and enjoyed by our family throughout the year, this home is ideal for couples, families, and discerning travelers seeking a restful and memorable getaway.

Luxury Pool Family Paradise-Siesta Key Beach/DT

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!

The Cottage (In the Country) Cozy, Quiet Retreat

Relax, unwind and unplug at this cozy Old Florida-style country cottage! Here you are away from it all in peaceful bliss... but if you want to go out for dinner, it's an easy drive into town! Located on a beautiful 5 acre plot, this guest home is the perfect spot for your Florida getaway! Just 30 minutes from Siesta Key and 6 minutes from the entrance to Myakka State Park, you can see the best of Florida, both the swamps and the beaches, all in one day!

Luxury 3/3 with Heated Pool, Spa, & Putting Green!

Experience luxury at this newly remodeled home with a brand-new pool, spa, and putting green. Centrally-located near downtown Sarasota, Siesta Key, Lido Key beaches, and St. Armand’s Circle, it features a full kitchen, 3 king bedrooms, 3 full bathrooms, outdoor dining, high speed internet, a 75” outdoor TV, fire pit, and EV charger. Pet-friendly with a fenced yard, pet crate, bowls & treats. License # VR24-00208

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. 🌴

DEC SALE! 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!