Pet-friendly holiday rentals in Sarasota County

A welcoming entryway showcases a simple wooden console table with small potted plants. Above, a serene painting depicting a boat complements the neutral wall. The view to the right reveals a sun room filled with natural light, providing a connection to the private backyard.

4.95 out of 5 average rating, 187 reviews

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

4.97 out of 5 average rating, 133 reviews

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.

5 out of 5 average rating, 6 reviews

Luxury 4B Home & Heated Pool, Resort for 10 guests

Minutes to Siesta Key Beach, this Sarasota home is made for effortless group getaways. Start your mornings by the private screened pool, unwind on the cabana daybed, and gather in bright open living spaces designed for connection. Enjoy a fully equipped kitchen, 3 full bathrooms, and a separate studio offering extra space and privacy. Centrally located with quick access to St. Armands Circle, The Ringling, and Mote Marine Laboratory & Aquarium—perfect for dining, culture, and family fun 🌴

The exterior of the villa is displayed, featuring a welcoming blue-green door and two large windows framed in white. A small potted plant accents the entrance, while a pathway leads to the door, surrounded by well-maintained grass and greenery.

4.86 out of 5 average rating, 137 reviews

Charming Villa 14 mins away from Siesta Key Beach

This villa close to Siesta Key Beach serves as the perfect escape for those looking to enjoy Sarasota. The property comes fully equipped with amenities such as a BBQ, outdoor umbrella, lounge chairs, beach chairs, pickleball rackets, washer/dryer and carport. Featuring 2 bedrooms, this charming home exudes a warm vibe. You can reach Siesta Key Beach, St. Armands Circle, and Downtown Sarasota in under 15 minutes, making it easy to explore all that Sarasota has to offer during your stay.

A distinctive triangular structure features large glass windows, showcasing vibrant lighting from within. The exterior is surrounded by landscaped greenery and decorative white stones, enhancing the inviting appearance. Palm trees and a tidy paved driveway contribute to the overall charm and unique architectural design.

4.95 out of 5 average rating, 242 reviews

Modern, Bright Downtown SRQ A-Frame West of Trail

Enjoy this bright, newly renovated unique pool home on a street with mostly waterfront homes featuring 4 beds & 3 baths, office area options, loft reading nook, Bosch appliances, bedroom skylights, artful light fixtures and fully fenced with heated pool. Central to & minutes from Siesta Key, St. Armand's Circle/Lido Key, downtown. Walk to the Sarasota Arts Museum, grocery, Southside and downtown Restaurants & shops, Selby Botanical Gardens, Bayfront Park, & Marina Jack. VR24-00157

A single-story home is showcased with a light exterior and grey roof. Blue shutters adorn the windows, while lush greenery and colorful landscaping enhance the front yard. A screened wraparound porch offers additional outdoor space. The property is bordered by a paved walkway.

4.95 out of 5 average rating, 108 reviews

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.

A bright pink flamingo float adorns the clear, inviting waters of the heated pool. Two white umbrellas provide shade for the striped lounge chairs nearby. Flower pots add a touch of greenery to the poolside area, which is enclosed by a white privacy fence.

4.95 out of 5 average rating, 133 reviews

Oasis by Siesta Key Beach and Downtown SRQ w/pool

Enjoy Sarasota in one of the most desirable neighborhoods by Siesta Key! Truly an elite location, take Siesta Dr down to the well-documented #1 beach in the US in around 10 mins. Flourishing Downtown Sarasota is just 5 mins away. The house features a brand new heated pool, fenced in back yard with pavers, open concept living, beautiful kitchen with everything you need, upgraded bathrooms and plenty of space for a big family. We look forward to hosting you and yours!

4.96 out of 5 average rating, 138 reviews

The studio features a modern kitchen with white cabinetry and a large countertop. A flat-screen TV is mounted on the wall, and natural light enters through sliding glass doors that lead to the private garden. A compact dining table and a plush blue ottoman add functionality.

Condo in Sarasota

Modern Studio · 5 min from Siesta Beach

Stylish ground-floor studio designed for couples or solo travelers, just a 5-minute drive from world-famous Siesta Key Beach. A great choice if you’re looking for a calm, well-located space with thoughtful comfort. Pet-friendly stay – $10 one-time pet fee per booking, unlimited pets. An ideal base for beach days, local dining, or a relaxed Florida getaway. About 1 mile from the property, guests may also enjoy access to a beautiful community pool that is heated.

An open living area features a large flat-screen television on a modern stand, complemented by a glass dining table with stylish stools. Natural light enters through large windows, while a contemporary ceiling fan hangs above, enhancing the inviting atmosphere of the space.

4.94 out of 5 average rating, 136 reviews

Hyde Park/Southside Village Modern 5 Star Home

BEST LOCATION/BEST VALUE ON 5 STAR HOME All 5 Star Reviews! Love This Location! Recently fully remodeled home. Three blocks to Southside Village, Morton's Market, fantastic shops and restaurants. Beautiful Arlington Park is down the street with pool, tennis, walking trails and dog park. 7 Minute Drive to Siesta Key or Downtown. **We love and welcome small dogs in our home. We need them declared at the time of booking. There is a small pet fee.

4.93 out of 5 average rating, 148 reviews

Cottage in Sarasota

Private Heated Pool Casita Near Downtown & Beaches

Built in 1925, Casita Verde blends classic vintage charm with modern comforts. This 2-bedroom, 1-bath home features a 55" flat-screen TV with HD cable and fast Wi-Fi. Relax by the private pool or enjoy peaceful evenings on the deck with your favorite drink. Pet-friendly and conveniently located near Downtown Sarasota on Bahia Vista, with an easy drive to Lido Key, world-famous Siesta Key, and I-75 for day trips and longer adventures. 🌴 Cert# VR24-00152

The exterior of a charming adobe-style home is highlighted, featuring a light blue facade and a decorative entrance. A pathway leads to the door, bordered by colorful plantings and a white picket fence. Tropical plants add to the serene ambiance of the front garden.

4.95 out of 5 average rating, 116 reviews

Casa de Zara| Downtown Sarasota- 5mi Lido Beach

Welcome to Casa de Zara! Immerse yourself in Sarasota history by staying in our quaint Adobe style home built in 1925 with a serene garden filled with plants and trees native to Florida. You will be 1 mile from Main St. and 4 miles to Lido Key. One block over you will find a fun filled park with tennis and pickle ball courts, a walking path and basketball courts. Less than a mile away is Bayfront Park which is perfect for watching sunsets!