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Winter Haven Retreat – Steps to Bay & Ringling

Tropical Paradise by Sarasota Bay – Walk to Ringling Museum, Asolo Theatre! Just a two minute walk to New College and its beautiful bayfront promenade, this 2,200 sq ft tropical retreat beacons you to unwind. Enjoy 3 very private bedrooms, an office area, spacious living room, and a huge fenced-in backyard perfect for kids and pets—all less than 15 minutes from Lido Beach and café-lined St. Armands Circle. Kayaks, hammock, grill, foosball, sandbox, basketball hoop, and more await your stay!

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Top 5% of homes: Lowest rates right now in Sept

Welcome to your perfect Sarasota escape! Ideal for families, sports teams, or beach lovers. Enjoy a heated private pool, screened lanai, BBQ, games, corn hole, playground, basketball court, and all the beach supplies you could need for fun in the sun (beach chairs, toys, cooler, etc). Enjoy Lido Beach, Siesta Key, Anna Maria Island, IMG Academy, Benderson Park, rowing, downtown Sarasota’s shops & dining. Whether you're here for sports, the beach, or relaxation, this home has everything you need.

Cozy Beach House Including King Size Suite !

Welcome to our beach home ! Located in a beautiful neighborhood where you can unwind & relax with the family after a long day at the beach. We are located only a short drive to the finest beaches in FL where you can find sand dollars with the kids & view breathtaking sunsets ! Play a game of pool, grill out on our patio, & enjoy our fire pit & enclosed pool !! This easy access one-level home sleeps up to 8 people. Conveniently located within minutes from groceries, restaurants, and attractions.

Private Sarasota Oasis with Fenced Yard & Gazebo

City of Sarasota Vacation Rental Certificate of Registration: 26-VR-000136 Welcome to your beach escape! Perfect for families & remote work! Mins to Lido Key Beach, Siesta Key, UTC Mall, Downtown, Ringling College of Art & Design, & dining. You’ll find everything you need for a stress-free stay- including a high chair, crib, toddler bed, beach gear, yoga mat, beach towels & umbrella, washer & dryer, fully equipped kitchen, high-speed WiFi, Smart TV, home office, & free onsite parking.

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Serenity Lake

Keep it simple at this peaceful and centrally-located place. 15 minutes from beaches this lovely apartment sits on a pond full of fish with a dock. Large pool ready for swimming and sunning. Charcoal and gas grill available. Beautiful upper deck to sit and enjoy the large mango tree and view over the lake. Golf cart available for evening rides. There is a large driveway for a boat. Swim and fishing accessories available. Minutes from I-75 - also near the famous Lakewood Ranch downtown.

Beautiful and Restful Sarasota Florida Retreat

This old Florida home has been updated with granite counters in the kitchen with newer appliances, ceramic tile, and wood flooring. There is plenty of room to spread out in the main living room and within the wood wall and ceiling finished gathering room. The backyard patio area is perfect for outdoor BBQs. The lush tropical landscaping provides the old Florida home feel. The best amenity is a semi-private outdoor shower with lush vegetation screening. Perfect for the outdoor enthusiast.

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Siesta Breeze, adorable New Beach Style Studio !

Stay at our renovated beautiful beach styled studio furnishing with a queen size bed as well as a full pull out couch bed. There’s a mini fridge, a two burner electric cooktop, a microwave, a toaster, a tea pot with complementary tea bags, coffee pot with complementary coffee and keurig with complementary Starbucks k cups. Free wifi and a 50 inch tv facing the bed. 2 minutes away from the air port, 10 minutes away from IMG Academy , 30 minutes from Anna Maria Island and siesta key .

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Lovely House in Sarasota Bay

Enjoy a stylish coastal bungalow in North Sarasota, just minutes from downtown’s restaurants, shops, and Sarasota Bay. Relax in modern comfort with central A/C, high-speed WiFi, and smart TVs in every room. Nearby, explore beaches like Siesta Key, Lido Key, and Anna Maria Island. The fully-equipped kitchen, comfortable bedrooms, and modern bath make for a relaxing stay. Plus, you’re close to top attractions like The Ringling Museum, Marina Jack, and more!

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!

Cute Bohemian House in quiet, gated community

This cute little house has 2 bedrooms as well as a sleeper sofa. There is also a pack n play for your little ones. All bed and bath linens are provided. There is a fully stocked kitchen with all the basic necessities As well as a dining area and sitting room. There is free wifi and ROKU TV. Guests are also welcome to use the washer and dryer. If you are looking for a fun getaway in a quiet, laid back community this is the perfect place for you.

The Aviator | 7 Mins From SRQ | Pool | Giga Wifi

Welcome to The Aviator—a unique 3BR/2BA pool home with aviation and military décor in a quiet Old Florida neighborhood. Just 7 min to the SRQ Airport, 6 min to the Ringling Museum, 5 min to USF, and 16 min to Downtown Sarasota. Enjoy a private screened pool, comfortable living spaces, and a central location close to beaches, dining, and attractions! Laundry facilities available for a small additional fee.

Kid-Friendly • Near SRQ • Sleeps 6–8

Relax at BayBreeze Cottage—just 3 miles from Sarasota Airport! This 2BR/2BA home sleeps 6 (up to 8 with queen air mattress, upon request) with a king bed & full-over-full bunks. Perfect for families, it features a screened lanai, fully equipped kitchen, WiFi, and two full baths (one with tub). Close to SRQ Airport, beaches, downtown, and top attractions. No pets. Ideal for work trips or getaways!