House vacation rentals in Downtown Sarasota

A quaint cottage features a vibrant red door, framed by lush greenery and colorful plants. The path leading to the entrance is bordered by neatly arranged brick landscaping, enhancing the inviting entrance to the home.

4.98 out of 5 average rating, 133 reviews

The Sweet Spot! Walk to DT & Free Trolley to Beach

Looking for the Sweet Spot in Sarasota? Look no further! This artistically updated cottage, nestled in the quiet, historic downtown neighborhood of Laurel Park is a just a short walking distance to some of the best downtown dining, shopping, arts venues and the renowned Selby Gardens. Take the free Breeze Trolley to Siesta Key and Lido beach. Relax in the private outdoor courtyard. It's is the perfect place for a couple's getaway, a family vacation, or a long term stay. So book now and welcome!

An inviting living space showcases a comfortable seating arrangement, including two black lounge chairs and a stylish dining area. Natural light floods through large windows, illuminating a decorative shelf filled with coastal decor. A circular rug adds a touch of warmth to the wood flooring.

4.96 out of 5 average rating, 129 reviews

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! 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 , 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. Take the nearby free Trolley

The spacious living area features a comfortable couch adorned with patterned pillows, a wooden coffee table, and colorful rugs. Natural light floods in through large windows, and an open layout connects to the dining area and kitchen, which is visible in the background.

4.97 out of 5 average rating, 120 reviews

Sunshine House, close to Downtown

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.

Home in Indian Beach-Sapphire Shores

A private heated pool is enclosed by a screened lanai, surrounded by lush tropical plants. Soft purple lights create a relaxed ambiance. Comfortable seating and dining areas are positioned nearby, inviting leisurely moments by the water.

4.97 out of 5 average rating, 155 reviews

ROYS PLACE private, tropical, romantic paradise.

NAMED #1 BEST AIRBNB WITH POOL IN SARASOTA BY TRIP 101 TRAVEL GUIDE FOR 2022, 2023, 2024. An exceptional vacation is a frame for an exceptional life. Offered for you, a romantic boutique home. Sarasota Chic decor, quality furnishings, lush tropical landscaping. Only property in urban Sarasota with your own private (EXCLUSIVE to you, NOT shared) CLOTHING OPTIONAL heated pool for tropical fun. One block walk to beautiful sunsets over Sarasota Bay. All tropical serenity yet close to everything.

The living area features a cozy sofa, two reclining chairs, and elegant decor. A TV is positioned above a media console, while a dining area is visible in the background. Large windows allow natural light to fill the space, highlighting the light wood flooring.

4.92 out of 5 average rating, 298 reviews

❤ Villa & Garden in Downtown ~ 5 Min to Beaches

Our bright and contemporary Heart Villa offers the quintessential Sarasota downtown and beach experience. It is nestled among tropical trees in a charming cul-de-sac in historic Laurel Park – right in the heart of downtown with loads of restaurants, boutiques, and sights on offer. Several fantastic beaches are just 5-mins ride away! And the villa's private garden is the perfect place to enjoy alfresco dining! We’ve poured our hearts & souls into this villa, it's our family business.

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, 164 reviews

Newly Renovated Ranch Minutes From Beach/Downtown

Newly renovated 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 WIFI. Grab the beach chairs and umbrella to enjoy Lido Key or Siesta Key Beaches both within a short drive. Wind down & grab drinks/dinner in downtown Sarasota or relax in the backyard. Several golf courses near-by or catch Orioles spring training at Ed Smith stadium within walking distance.

Home in Indian Beach-Sapphire Shores

A private courtyard featuring a heated pool is surrounded by lush tropical landscaping. Comfortable lounge chairs are positioned beside the pool, and a small fountain adds a soothing element. A cozy seating area is visible near the entrance to the adjoining building.

4.94 out of 5 average rating, 125 reviews

Pool Courtyard, patio w/ fire pit, 2 mls downtown

Enjoy this unique courtyard-style Spanish colonial home just steps to Sarasota Bay and 2 miles from downtown. The property consists of a 2 bed / 1 bath main house AND a detached studio. Everything pictured is yours to enjoy, nothing is shared. The houses are separated by a quaint & private pool courtyard w/ outdoor shower. Capture a photo of the local peacocks, eat fresh mangos from the yard, catch a sunset over the bay, or enjoy the sun by the pool listening to the Zen fountains.

4.96 out of 5 average rating, 102 reviews

The Wisteria Oasis W/ heated pool & hot tub

Come Relax with your family at this peaceful 3 bedroom cottage, It has a private fenced in backyard w/ new heated saltwater pool, hot tub, hammock & swings,and a fire pit to make s’mores! Yes its stocked with beach gear and a short drive to the beautiful siesta key and lido key beaches. Also minutes from the Bayfront park where u can watch amazing sunsets and the downtown sarasota dining spots! Arlington park is in the neighborhood with trails- play area- pool- outdoor gym.

A modern living area features a gray sectional sofa with white throw pillows, positioned next to a light area rug. A sleek coffee table holds a yellow tray, and a round mirror is mounted on the wall above. Green plants add a touch of nature, enhancing the space.

4.91 out of 5 average rating, 263 reviews

Cozy Getaway Home in Sarasota Near Beaches & More!

Escape to our peaceful home in Sarasota. Conveniently situated near our famous beaches, UTC, Benderson Park, downtown, and only within a mile of grocery stores and other shops. Enjoy outdoor moments on the patio and spacious yard. Modern amenities include high-speed internet, smart TVs, and a well-equipped updated kitchen and workspace. Washer/dryer on-site as well. Your gateway to relaxation and Sarasota's charm awaits! Please reach out if you have any further questions.

Home in Downtown Sarasota

A welcoming entryway features a bright door with a small window and a decorative hanging piece. Light-colored walls surround a cozy seating area with a modern sofa. A simple side table holds a lamp, and framed artwork decorates the walls, complemented by indoor plants.

4.92 out of 5 average rating, 256 reviews

*Downtown home 10min. drive to beach; walk DT*

In the heart of Gillespie Park, this bright & spacious home is a 10 min. drive to Lido Beaches and within walking distance to downtown shops, grocery, farmer's market, opera house, restaurants, bars, live music, tennis, parks, antique shops and performing arts. Old Florida bungalow on the outside, inside, it's updated with new appliances and bathrooms. A banyan tree offers private, shady repose on the back deck w/grill and dining area. Message me for room availability.

The front exterior of the home features a light grey facade with stone accents. Two comfortable chairs are positioned on the covered porch, inviting relaxation. A brick driveway with ample space leads up to the entrance, surrounded by landscaped areas and a peaceful neighborhood view.

4.93 out of 5 average rating, 194 reviews

Sea-esta Cottage- Cheerful 2bd/1ba w/ free parking

Experience ultimate relaxation in this serene and stylish rental. A brand-new home in the heart of Amish Village, Pinecraft. Two cozy bedrooms with plush bedding and soothing coastal decor. Sip your coffee on the front porch, immersed in the tranquility of this idyllic neighborhood. Take a short walk to Yoder's Restaurant, Coastal 98 Cafe, and the Pinecraft Ice Cream Shop. Just 6 miles to Siesta Key and 7 miles to Lido Beach for endless coastal adventures.