Pet-friendly holiday rentals in Downtown Sarasota

Cozy 2 Bedroom Private Unit

This thoughtfully designed space offers a cozy ambiance with all the comforts you need for a relaxing stay. Step inside to find a warm and welcoming living area, perfect for unwinding after a day of exploring. The well-equipped kitchen allows you to prepare your own meals, complete with essential appliances and utensils. The unit's prime location offers convenience and easy access to local attractions, restaurants, and shops. We can't wait to welcome you and create lasting memories together.

Early Chkin, Elevator-4th fl 2mins-DT, 7mins-Airpt

Beach ready Apt!! Echo/white noise machine Beside Ringling College! 2 minutes from downtown Sarasota 7 mins - Airport Corner Apt Steps to the elevator 2 bicycles & 2 escooters Escape the ordinary and immerse yourself in an extraordinary stay at our unique Airbnb that's on a main road . 60+ amenities from a secure room safe to a luxurious, indulgent bed. Essential amenities such as grocery stores/pharmacies/ & CVS. less than a mile away. Send me a message if you have any questions .

Updated Ranch Near Beaches/Downtown - Pet Friendly

Updated cozy home with all new furnishings and appliances. 2 bedrooms 1 bathroom with an eat-in kitchen, sun room, and comfy living room. Stream shows or work virtually with our high-speed Wi-Fi. Grab the provided beach chairs, umbrella, and cooler to enjoy Lido or Siesta Key Beaches, both within a short drive. Wind down & grab drinks/dinner in downtown Sarasota or relax in the fully fenced private backyard. Enjoy several nearby golf courses, or catch Orioles spring training at Ed Smith Stadium

Downtown Bungalow-Beaches, Dining, Shopping, Shows

Welcome to The Shady Place! This charming, family-friendly bungalow is a quiet, private oasis in the heart of downtown. Here, you’ll be close to all area beaches including world-famous Siesta Key-rated by Trip Advisor as the #1 beach in the US, SRQ airport, golf courses, Legacy Trail, UTC mall, Mote Aquarium, Bayfront Marina, The Bay park, St. Armands Circle, Robarts Arena, Ed Smith Stadium-spring training home of the Baltimore Orioles, & Downtown Sarasota’s restaurants, activities & nightlife.

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.

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.

Sarasota Getaway Guest House

Cute guest room with private access, featuring a comfortable queen‑size bed, spacious bathroom, coffee bar with Keurig, microwave & mini fridge. Enjoy a short walk to downtown shopping, dining, live music, Whole Foods, galleries, and fine shops. Gillespie Park is just across the street with tennis, pickleball, basketball, dog‑walking areas, & walking/running paths. You’re only minutes from Lido Beach, St. Armands Circle, Mote Marine, museums, theaters, and Sarasota’s top coastal attractions.

Beautiful Historic District Walkable Near Marina

My historic building was built in the 1950's and has clean character and ambiance. Walking distance to Whole Foods/Publix, fabulous restaurants, diverse shopping options, performance theaters, movie theaters, nightlife, public transport, boat/water activity rentals, parks, spas, and a short distance to Siesta Key & Lido beach or Sarasota airport. You’ll love my place. It is good for couples, solo adventurers, and business travelers. I have lots of regulars who come back time and time again.

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

Sarasota 2B/2B Near Siesta Key/Arlington Park/SMH

This newly renovated property is equipped with 2 bedrooms and 2 full bathrooms, full kitchen with all appliances, washer/dryer, screened wraparound patio, and fenced-in yard. Safe and beautiful walking neighborhood - 15 minute walk to Arlington Park and Recreation Center. 7 minute walk to Sarasota Memorial Hospital and Southside Village restaurants & shops. 15 minute drive to Bayfront Park, Selby Botanical Gardens, Marina Jack, St. Armand's/Lido Key and Siesta Key Beach.

Perfect Florida location: Craftsman Carriage House

Beautiful 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.