Family-friendly holiday 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

Indoor spaces · Kitchen · Condition

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

Family · Indoor spaces · Accuracy

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

Kitchen · Indoor spaces · Sleep quality

Beachside Bliss: Family Paradise/Siesta Key3BR/2BA

Escape to this stunning, fully renovated 3BR/2BA home in the prestigious Gulf Gate Neighborhood, just 5 minutes from Siesta Key Beach – ranked the #1 beach in the U.S.! This spacious and airy retreat is designed for relaxation and making unforgettable memories. Enjoy an impeccably styled interior, modern amenities, and a prime location close to Sarasota’s best attractions. Indulge in top-rated restaurants, vibrant shopping centers, and endless beachside adventures—all just around the corner

Family · Indoor spaces · Checkout

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

Kitchen · Indoor spaces · Accuracy

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

Kitchen · Family · Nearby

Dog Friendly -4 Bed 2 Bath w/ HTD Pool (Sleeps 13)

✨ Fully Renovated & Stylish! ✨ Family & Dog-Friendly | Single-Story | Private Saltwater Pool | Secluded Backyard. Enjoy the charm of Sarasota in our completely updated home off University Parkway. Bright, open spaces with new furniture, perfect for relaxation. Features a heated saltwater pool in a private, fenced yard. Close to beautiful beaches—10 miles to N. Lido Beach and 13 miles to Siesta Key Beach. Conveniently located 4 miles from SRQ Airport, ideal for your next memorable get

Indoor spaces · Kitchen · Quiet

1 House 1400sq. ft. 12 min from Siesta Key!

12 min. from Siesta Key Beach!! Perfect cozy vacation home in quiet, friendly neighborhood. Central to lots of shopping/restaurants. 1-king, 1-queen, bunk beds w/ 1-full & 1-twin. Dog & cat friendly w/ large private fenced yard, & 1-men's & 1-women's bike. Air hockey table w/ board games & pool toys. Fully loaded kitchen & W/D. Spacious living w/ large sectional, swing chair, & all bedrooms come w/ TVs & free Netflix & Hulu. Looking forward to hosting you! Message me anytime w/ questions.

Indoor spaces · Kitchen · Hospitality

Backyard Oasis, Htd Pool/Hot Tub, Beaches, No Fees

Welcome to Siesta Fiesta, where dreams of relaxation become reality. With the backyard heated pool and hot tub, you have your own oasis to channel inner peace. If you’re feeling froggy, hop over to the beaches, take a kayak tour through the mangroves, a beautiful chartered sunset cruise, or try some of the local eateries that guests rave about! Whether you want to stay in, or go out, this home offers you everything you could need or want and will satisfy for pure relaxation or adventure!

Family · Kitchen · Comfort

The Key Lime Cottage 2 miles from Siesta Key Beach

Great location. 2 miles from the # 1 rated Beach in America , Siesta Key . The cottage is near several other beaches as well. Walking distance to a Publix grocery store and 5 good restaurants. 1 hour from Tampa and 2 hours from Orlando. 15 min from Sarasota Airport. The Cottage is totally updated with new stainless steel appliances in kitchen and inside completely repainted Sept. 2026. Both beds are new and comfortable. Quite neighborhood and great for walking .

Family · Kitchen · Sleep quality

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!

Kitchen · Indoor spaces · Quiet

Cottage on Siesta Key Beachside & Stunning sunsets

Come experience Siesta Key and relax in our beachside cottage. It is sure to refresh you , whether you prefer an incredible one of a kind sunset or a long leisurely walk on the beach with the cool sugar white sand beneath your toes! This is an escape you deserve. The pool is beautiful and conveniently located on your stroll to the beach. If you enjoy music , we are close to several places you can sit & enjoy under the Tiki Huts with refreshments!

Family · Indoor spaces · Access