
Holiday houses in Sarasota County
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Top-rated holiday rentals in Sarasota County
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FlipFlopsOn III • ½ Mile Siesta Key • Walk to Bay
Experience life 4 blocks from the Gulf, ½ mile to Siesta Key — America’s #1 Beach. With effortless access to Sarasota’s dining & arts scene, Siesta’s white sand beaches, St. Armand’s, & Gulf Coast adventure! 2BR boutique bungalow • Sleeps 6 • 4 beds Situated in the coveted Coastal District (‘West of Trail’) — chef kitchen, beach gear, Smart TVs, marble spa bath, laundry, fast Wi-Fi. Grill lobster under stars, unwind in your tropical garden, & walk palm lanes to cafes, and waterfront sunsets.

5 Star! Walk/Bike DTN ~ 5 mi to Lido Beach Pets Ok
Bright & Comfy Downtown Home | Walk to Main St, Near Trolley to Lido Beach & St Armands. Centrally located in a quiet downtown neighborhood along the Legacy Bike Trail & Payne Park, this updated 3BR/2BA home is clean, cozy, and filled with coastal charm. Enjoy a screened-in lanai, a large, fenced backyard, WiFi, Smart TV with YouTube TV, BBQ, beach gear, washer/dryer and carport. Pets welcome! Prime Location: 1 mi to Main St dining. 2 mi to waterfront dining and boat tours. 5 mi to Lido 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.

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

Sarasota Florida -Wild Orchid Creek Cottage Home
Come enjoy old Florida living at this completely renovated cottage style home on nearly seven acres. Relax and unwind in this 1000 square foot private home with king bed and queen sleeper to accommodate up to four people. Open concept living, dining room and full kitchen. Laundry facilities available. Equipped with WiFi and direct tv. While enjoying the private backyard space, it is common to spot abundant wildlife and wildflowers. Wild orchids in many of the oak trees bloom in early summer.

Private Heated Pool Retreat for Two Families
🌴 Welcome to your private Sarasota escape - designed for easy, extended stays, where two families can relax together around a private heated pool. With generous living spaces and thoughtful touches throughout, the home balances comfort and connection. Located minutes from Siesta Key, Lido Beach, and downtown Sarasota, and within walking distance of a park with playground, public pool, courts, fitness areas, and scenic trails. Relaxed, comfortable, and ideal for memorable family getaways.

I -75 exit 210 5 minute private sleeps 2 no pets
Off I-75 exit 210. one bedroom apartment tucked away on 5 acres Sarasota. 5 minutes off I -75 in a private neighborhood 8 minutes from restaurants and shops at University Town Center and 20-30 mins from Siesta Key and Lido Beach. Has 1 bedroom, 1 bath apartment has a queen size bed. Living room with love seat, TV. Equipped with a refrigerator, double burner cook top, coffee pot, toaster, and microwave.The apartment also has a washer and dryer and a carport for parking No pets!

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

Beautifully Remodeled Home with Pool Near Siesta
It’s all about Siesta! Newly remodeled, 2 bedrooms, 2 baths, heated pool home is located in the Gulf Gate Estate neighborhood. 2,5 miles from the famous Siesta Key Beach. Great split plan bedrooms and bathrooms. High-speed Wi-FI. Located less than a mile from Publix Grocery, Gulf Gate shopping mall, grocery store, restaurants, cafes, pubs. Walking distance from the nearest convenient/gas station-7Eleven (5min). Parking for up to 3 cars maximum. Must be at least 25 years old.

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

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!

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!
Popular amenities for Sarasota County holiday rentals
Other great holiday rentals in Sarasota County

Paradise Villa- Sarasota

Spacious Cozy Tropical Retreat!

Botanical Bungalow at THE BAY

The Palms Away

"Little Siesta" - Farm home near Terra Nova

Sarasota House• Fenced Yard• King Beds• EV Charger

J&K Dream Home in Sarasota

The Ashton Retreat
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- Anna Maria Island
- Siesta Beach
- Crescent Beach
- Captiva Island
- John's Pass
- Turtle Beach
- Coquina Beach
- Vinoy Park
- Lido Key Beach
- Caspersen Beach
- Tiny House Siesta
- Bean Point Beach
- Cortez Beach
- Jannus Live
- Anna Maria Public Beach
- Manasota Key Beach
- River Strand Golf and Country Club
- North Beach At Fort DeSoto Park
- Englewood Beach
- The Don CeSar
- Lakewood National Golf Club
- Myakka River State Park
- Tropicana Field
- Img Academy
- Things to do Sarasota County
- Things to do Florida
- Entertainment Florida
- Sports activities Florida
- Wellness Florida
- Food and drink Florida
- Tours Florida
- Art and culture Florida
- Nature and outdoors Florida
- Sightseeing Florida
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