Holiday rentals with a fire pit near Crescent Beach

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.

Sweet, pet friendly Siesta Suite

Sweet spot with the best of both Sarasota and Siesta Key - your private oasis for relaxing and rejuvenating. Whether you choose to chill or find adventure it is all within reach! Siesta Key beaches, Village with shops, restaurants, and bars; Sarasota culture, arts, and entertainment; quaint Gulf Gate shops and eateries ...the possibilities truly are endless. Regardless of how you choose to spend your time here, you will be sure to create lasting memories to share and leave wanting more.

Luxury Villa with Pool, Game Room, Near Beach

Welcome to your tropical luxury escape! Spacious living flows to the heated pool, game room and sunny patio—perfect for family fun. • Bedrooms: 4 private suites, plush linens to ensure restful nights. • Location: Quiet neighborhood just minutes from the sandy beach, dining and shopping hotspots. • Heated pool & sun loungers • Arcade-style game room • Fast Wi-Fi & 5-star cleanliness • Pet friendly with fenced yard Have questions? We reply in under an hour—book your stay today! VR24-00060

@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)

Beach Retreat•Renovated & Heated Pool•Near 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.

Mid-Century Circus Charm Near Downtown Sarasota

Retro circus romance & mid-century style near downtown Sarasota. ✅ Main Street, Downtown Sarasota 2 miles - 6 mins ✅ St. Armand’s Circle: 4.5 miles - 15 mins ✅ Lido Key Beach 5 miles - 15 mins ✅ Siesta Key Beach: 6 miles - 18 mins ✅ Downtown Bradenton 12 miles - 25 mins ✅ Bradenton Beach 14 miles - 30 mins ✅ Casey Key 16 miles - 30 mins ✅ Airport: Sarasota–Bradenton International Airport 6 miles - 12 minutes

Peaceful waterfront home

Take it easy at this unique and tranquil getaway. Nestled alongside a serene canal, our home is a sanctuary of tranquility and natural beauty. From the moment you step onto the property, you are met with charm and allure that only canal front residence can offer. For those who enjoy outdoor activities, the canal provides a perfect venue for kayaking, fishing and lounging in our cocktail pool and hot tub. Surrounding sliding glass doors opens up to 3 separate patios.

Home near Anna Maria Beach w/ Hot Tub + Fire Pit

Come find a space away in this 1 bedroom Guest House with a private patio and inflatable hot tub located less than 15 Minutes away from Anna Maria Island Beach. Enjoy all that the area has to offer, and come home to the private ambience of an outdoor fire pit and relaxing hot tub, or play a fun game of corn-hole on the back patio. (The outdoor area is completely enclosed for your exclusive use) The home is a quaint 627 square feet in a safe and friendly neighborhood

City Garden Cottage

City Garden Cottage is a cozy and comfortable cottage located in the quiet Laurel Park neighborhood in Sarasota, only a few blocks from downtown. The studio is surrounded by lush gardens and trees with a Hot Tub. Inside, you will find a kitchenette equipped with a coffee maker, toaster, refrigerator, and hot plate. The studio also has a flat-screen TV, a queen bed & private bathroom. There is also shared use a gas grill, fire pit and Hot Tub included with the rental.

Cozy Studio - quick walk to #1 Siesta Key Beach!

Recently renovated and updated! Adorable studio just steps from Siesta Key Village, and a quick walk to the beach. Spend your day exploring the key, swimming in the ocean, and experiencing the local restaurants and shops. Enjoy coffee in the mornings on the patio, and use the available bikes to catch a beautiful sunset each night. **Please note: - No excessive noise or Parties/Events will be allowed** - No Smoking inside the unit** - Quiet hours from 10 PM to 7 AM**

Florida Cracker Cabin on cattle ranch/Myakka River

We are located in Myakka City, FL, which is a short drive to Siesta Key and Lido Beach and Sarasota! Enjoy a peaceful stay in our newly built, unique, air-conditioned cracker cabin. The cabin sleeps 4 guests and is located in the middle of our 1,100 acre working cattle ranch. Step outside and you are right on the Myakka River and can sit by the fire-pit at night and enjoy the sounds of nature. While your visiting, enjoy a kayak down the Myakka River.

Luxury Canal-Front Home + Heated Pool Near Beach

This is a thoughtfully renovated canal-front residence near Siesta Beach. A private pool and screened patio offer a refined and tranquil retreat with direct canal views. Bright interiors and carefully curated details create an atmosphere of timeless, understated luxury. Just an 8-minute walk from the world-famous beach, yet surrounded by complete peace and privacy. This home is designed for guests who appreciate discreet luxury and elevated comfort.