Family-friendly vacation rentals in Sarasota

Free Heat Pool+Grotto+Spa~Pickleball~Golf~KidSuite

Modern, Stylish, & Family-Friendly! ~New Custom GROTTO WATERFALL Pool & Spa! ~Massive "KIDS SUITE” with Full-over-Full bunk + Twin bed trundle + Queen - sleeps up to 7 just in this room! ~5 Bedrooms with TVs, 2.5 Baths, 8 Beds (1 floor bed) ~FREE heated POOL+SPA, PICKLEBALL, GARAGE GAMING+TV, PUTTING, FIRE PIT, OUTDOOR COVERED DINING, and KIDS PLAYGROUND! ~Private, Fenced Yard, Perfect for Families! ~4-6 Car Parking! ~12 mins - Anna Maria Island Beaches ~5 mins - Target Sorry, no pets allowed.

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.

Family Fun•POOL•Sleep 14•Game•SRQ, Ami &Beaches

Get ready for nonstop fun at Paradise Island - an amenity-packed retreat in Sarasota! Whether you're in the heated pool or hot tub, playing mini golf, enjoying a family game night, relaxing by the fire pit, or grilling barbecue in the backyard, there’s something here for everyone. This vibrant 4-BR, 2-bath home sleeps up to 14 guests and is just 5 minutes from the airport and a short drive to world-class beaches. BOOK YOUR STAY TODAY - The Ultimate Retreat for Family Fun and Forever Memories

The Wisteria Oasis W/swings, heated pool & hot tub

A Florida wellness retreat>>> Discover the charm of our delightful cottage, exceptionally placed amidst lush greenery! The interior offers an inviting ambiance with its plush, comfortable furnishings and a well-equipped kitchen with an espresso machine. Quietly nestled away from the hubbub of city life, our cottage offers a tranquil escape yet is in close to local attractions. Relish the day exploring charming seaside villages and beaches or simply bask in the serenity of your private haven.

Luxury 3B/3B waterfront home w/ pool + boat access

Escape to this luxurious 3BR/3BA Sarasota sanctuary! 5 minutes from Siesta Key, this Mid-Century Modern gem sits on a canal with direct Bay access (no bridges). Dive into the private pool & spa, lounge on the 1,000 sq ft porch, or relax inside on cozy furnishings. Includes a private dock, kayak/SUP/canoe, bikes, and a massive driveway for boat trailers. From the hanging bed swing to the gourmet kitchen, every detail is designed for your dream waterfront getaway. Your Florida paradise awaits!

Living The Dream: Heated Pool + Mini Golf +Swings

BNB Breeze Presents: Living The Dream A purpose-built luxury family vacation home designed by parents for unforgettable stays. Enjoy swing dining chairs, a glowing neon moss wall, backyard putt-putt, and a free heated saltwater pool (Nov 21–Apr 1st). 15 minutes to Siesta & Lido Key Beaches. ✔ Private heated saltwater pool ✔ Backyard mini golf & outdoor games ✔ Luxury covered lanai w/ high ceilings ✔ Super kid-friendly (toys, Pack ’n Plays) ✔ Jura Espresso Machine ✔ 65” Frame TV w/ YouTube TV

Resort Style Retreat - Tropical Oasis - Beaches

Book your vacation knowing that a one-of-a-kind experience awaits you. This home is well-equipped for travelers of all ages, and features unique spaces and amenities throughout. The ultimate home for families and friends. Seasoned professionals in hospitality, we've worked tirelessly to create a memorable experience for guests of all ages. Book now for some fun AND relaxation! 🌴Fire Pit 🌴Sanded Beach Areas 🌴Pool Table 🌴Lighted Splash Pad 🌴Games and Books 🌴Coffee Bar 🌴Yoga/Weights

Private Oasis: Mini Golf and firepit. 2 king beds.

Enjoy an unforgettable stay in this cozy home. The property features 3 comfortable bedrooms, 2 full bathrooms, and a large outdoor area designed for relaxation and connection. The real highlight is the amazing backyard: Fully furnished with high-quality outdoor furniture Fire pit for cozy nights under the stars Mini golf for fun without leaving the house Kid-friendly play area, safe and entertaining Stylish pergola with hanging chairs to unwind and enjoy the fresh air No Parties or Events!

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

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.

Casita Lantana, a 1925 cottage in a Tropical Oasis

Welcome to my original 1925 Casita, built in the heyday of the John Ringling era. We are centrally located between Sarasota, Lakewood Ranch, and Bradenton, making it an ideal place to explore all the area has to offer. Getting around is easy since we are located very close to the Ringling Museum of Art. Plus, it is only a short 15-minute drive to downtown Lido Beach and St. Armands Circle.

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. 🌴