Holiday rentals in Downtown Sarasota

Cozy and Private Studio Near Downtown & Beaches

Welcome to your private Sarasota retreat! This cozy and well-appointed studio offers everything you need for a comfortable stay—spacious bath, kitchenette, washing machine, WiFi, cable TV, a comfy recliner, work desk, and wall A/C. Step outside to a fenced backyard with a BBQ grill, perfect for relaxing. Enjoy a private entrance and driveway parking. Just 15 minutes from Siesta Key Beach and 10 minutes from downtown, you’re close to shops, dining, and the Legacy Trail. Relax, unwind, and enjoy!

Sarasota Getaway Guest House

Fully private & not shared with others Seasonal rates commence Nov 1 2023 - April 30, 2024 Longer Term Lower Rate Rentals commence May 1, 2024 - Nov 24 (Long Term rental rates available - please contact) Enjoy the luxuries of staying in the Gillispie Park area Dog Park, Tennis, Pickleball...... Walking distance to downtown where guests can find wonderful dining, entertainment, Saturday morning Farmers Market and much more Close to beaches and Arts and Entertainment and St. Armands Circle

Duplex - just mins to Siesta Beach - Pet Friendly

This is a 2/1 in Sarasota's Historic Laurel Park that offers a great downtown and beach experience! Walk/bike to historic downtown with shops, restaurants, bars, boutiques, parks, and music/theater. Minutes from the best beaches in the U.S. Enjoy the lanai & fenced backyard for privacy . Grill & enjoy your favorite beverage while watching your favorite show on the lanai ! Enjoy taking your pet for a walk & check out the historic homes in the area! Short term rental number VR24-00222

SUPER CLEAN 100% Private Downtown Location

A very private, quiet and secure space with a new comfortable Queen size bed, best of linens, 100% private attached bathroom and shower. Walk to downtown, waterfront and Payne Park. Complimentary bicycles, beach cooler, beach towels and umbrella! 100 Meg WiFi, large desk, LED TV. Delightful husband/wife "Superhosts" tend to your every need including complimentary bottled water, Starbucks coffee and Bigelow tea. We utilize the Airbnb and State of Florida anti-bacterial cleaning protocols.

MG Tropical Stay. Fully private, no shared spaces

Welcome to your modern Guest Suite in Sarasota – Adults Only, Private & Peaceful 🌞 Enjoy your own private space—no shared areas—with a separate entrance and parking for two cars. The suite includes: A cozy queen bed A full bathroom A well-equipped kitchenette with a microwave, small refrigerator, coffee maker, and 2-burner cooktop A secluded outdoor patio with a solar shower, ideal for rinsing off after a beach day A mini-split A/C unit to keep you cool during Florida’s sunny days

Perfect Florida location: Craftsman Carriage House

Beautiful, recently built accessory dwelling in downtown Sarasota designed to match and complement our historic 1920s bungalow main house, which can be booked separately on AirBnB. The 1BR/1BA carriage house apartment has all modern amenities, with a dedicated garage parking spot and a lovely outdoor porch. The carriage house features Craftsman-style details and is available for short- or long-term stays. Locally-based property management team on-call to ensure a pleasant stay.

Unique tropical stay - 5 minutes to Siesta Key

Welcome to “The Stream” — a hidden tropical retreat tucked away in the heart of Sarasota. This one-of-a-kind space offers the perfect blend of seclusion and convenience. Just 5 miles from the world-famous Siesta Key Beach and 3 miles from downtown Sarasota. Stroll or bike to nearby cafés, acclaimed restaurants, boutique salons, Publix, Trader Joe’s, CineBistro, and more. Whether you’re here to unwind or explore, “The Stream” is your private paradise.

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. 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 and fire pit included with the rental.

Maggie's Hideaway

This adorable little bungalow is hidden away in one of Downtown Sarasota's oldest historical neighborhoods and only a couple miles from Sarasota Bay and surrounding beaches. Beautiful Lido Beach is only five miles west, Siesta Key is seven miles southwest, with Benderson Park being only seven miles east. Fabulous shopping and world class dining is plentiful in this downtown community. There is plenty to see and do in Sarasota - Come see us!

Studio Minutes to Siesta key, Lido Key, and SMH!

Enjoy sunny Sarasota, FL in our studio apartment. Located between Siesta Key and Lido Key. You can walk to Southside Village, Sarasota Memorial Hospital (SMH) and Arlington Park. Enjoy the beautiful neighborhood and easy access to Legacy Trail. Approximate driving times to popular local destinations: Siesta Key - 10 minutes Lido Key - 14 minutes SRQ airport - 15 minutes St Armands - 10 minutes Downtown - 7 minutes

Downtown Apartment w/ Pool, Gym, & Coworking 329

This 2/2 apartment features an oversized kitchen with island, slider with views of Downtown. Primary has a king bed and en-suite bathroom. 2nd bedroom has a twin bed with twin trundle. Shared amenities include: gym; sunset deck; massive roof deck with heated pool; gazebo with big-screen TV, fireplace, wet bar, dog run and access to the adjacent Cowork office space building. Also on-site is a full service cafe.

Centrally Located Beach Suite - Fenced in Backyard

Welcome to your private guest suite in the heart of Sarasota - just minutes from Siesta Key, St. Armands Circle, and the best beaches, shops, and dining in town. Thoughtfully designed for comfort and convenience, this studio-inspired suite is the perfect home base for your Florida getaway. Whether you’re here to soak up the sun, explore Sarasota’s vibrant culture, or simply relax, you’ll feel right at home.