Holiday rentals with a fire pit near Crescent Beach

Private Island Old FL Waterfront Heaven on Earth

Discover the hidden secret of "Terra Ceia Island" (Heaven on Earth.) This 3 bed / 2 bath completely remodeled and charming A frame home offers breath taking sunrises from the bayfront private dock. Imagine enjoying your coffee in adirondack chairs while the sun rises over the Tilette Bayou. Enjoy bike rides through the old Florida country side (Bikes included). And rent a boat and cruise the pristine waterways around the keys. This home has everything you need for relaxation, peace, and fun.

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.

Bike to Beach Double King Suites, Pool & Mini Golf

Escape to the Salt & Sol House- a luxe coastal boho getaway just minutes from the white sands of world class Siesta Key Beach. This newly designed vacation rental offers everything for your perfect Florida escape. Enjoy indoor outdoor living, a heated pool, private putting green, bikes for exploring, hammocks in the shade, and twinkling string lights that create unforgettable evenings. Experience pure relaxation with resort-style amenities and luxury in paradise. BONUS: We are pet-friendly!

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.

@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)

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.

New listing - Beach Penthouse w/ Pool

New Listing, Onyx Penthouse - Siesta Key Vacation Rental Resort-like penthouse only 500ft to private beach access and Siesta Keys whitest sand. Amenities include - fully appointed pool area, alfresco dining and lounging, in-house elevator, 14ft ceilings, open sun and covered private balconies, 4-hole putting green, top floor unit, and wraparound ocean view balcony (partial). Book your getaway now! - Tollbooth by AirbnbCorpMiddlemen, but this property is from GertrudeRentalsSiesta

Siesta Key Condo: Beach, Pool & Village Fun!

Escape to paradise in our newly renovated 2-bedroom condo, perfectly situated a block from Siesta Key Village. Enjoy the convenience of walking to bars and restaurants, plus two parking spots if you prefer to drive. Relax by the community heated pool or take an 8-minute stroll to the award-winning beach. Explore the area using the free trolley, or venture to downtown Sarasota. This dog-friendly condo offers Wi-Fi, a smart TV, in-unit laundry, and essential home and beach gear.

Cozy Coastal Getaway 2 min Walk to Beach & Village

Steps away (2+ min walk / Beach Access #3 & #4) from the #1 beach Siesta Key and to the many restaurants, bars, and shops in local village. Relax & recharge at this peaceful cozy coastal 1bd /1ba Siesta Key condo w/ queen Sofa sleeper. Fully stocked upstairs unit w/ private balcony & great natural lighting + a community deck w/ grill & fire pit. Beach gear provided: beach chairs, umbrella, cooler bags, sunscreen, toys. The warm sun, white sand & ocean waves await you!

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**

Siesta Key | Heated Pool | Sauna | Family & Pets

☞ Sauna, Fire-pit, BBQ (gas) ☞ Giant Outdoor Chess♟️ ☞ King & 2 Queen Beds ☞ Ample Parking (RV, Boat, etc) ☞ Fast WiFi 🛜 ☞ 4 Smart TVs (largest 85 inches) ☞ Gourmet Kitchen Main side ☞ Kitchenette on Guest side ☞ 2 Onsite washer + dryers ☞ 2 Outdoor Showers 》30 mins to airport 》2 mins to Siesta Key Beach Bike to America’s #1 beach, morning coffee runs, sunset rides, live music, ice cream, shops or any of the amazing restaurants in Siesta Key village.

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.