Condo holiday rentals in Sarasota County

A modern bedroom features a spacious bed with crisp linens and a light-colored throw. A wooden dresser stands against the wall, and a framed artwork of a cow adds a touch of character. Subtle lighting from the bedside lamps enhances the inviting atmosphere.

4.86 out of 5 average rating, 348 reviews

[Beach Retreat] modern condo +5 min. walk to beach

5 min walk to beach and bikes onsite to rent.. Relax and recharge at this beautiful modern two bedroom Siesta Key condo. This is a fully remodeled second floor end unit with no unit above. The open layout provides excellent light throughout. Wonderful tile wood floors and a private screened in patio to sip your morning coffee. The warm sun and white sand beach awaits... beach gear (2chairs, towels, beach wagon)included complimentary -plus 2 beach cruisers to rent ($40 each per stay)

Superhost

A bright studio features a spacious queen-sized bed adorned with a light-colored blanket and a blue accent pillow. A kitchenette is visible in the corner, equipped with a mini fridge and a microwave. Soft lighting emanates from two bedside lamps, enhancing the inviting atmosphere.

4.87 out of 5 average rating, 134 reviews

Luxury Queen Suite just steps to Siesta Key beach

Wake up with a fresh cup of coffee, then take a short stroll to Siesta Key’s world-famous white sands. Feel the cool, powder-soft quartz beneath your feet as the ocean breeze melts your worries away. Spend your days basking in paradise, swimming in crystal-clear water and watching breathtaking sunsets. Afterward, return to your spotless Queen suite, refresh, and enjoy Siesta Key’s vibrant nightlife. A true beach oasis in the perfect location—book now before it’s gone! Note: No parking available

4.98 out of 5 average rating, 131 reviews

Lovely 2-Bedroom Condo, 7 min from Siesta Beach

Welcome to our beautiful condo, which is located just 4 miles to Siesta Key! Enjoy Vamo Park, just steps from our door, where you can launch a kayak or paddle board. Fishing is also allowed from this location. There are also picnic tables at the park where you can enjoy sunset. Our condo is fully equipped with all the necessary things you need. Beach chairs, shops, theaters, gyms, and the legacy trail, Sarasota Sharks Inc. Plus more. These are just a few of the things available in the area.

4.83 out of 5 average rating, 115 reviews

LJ's Cottage 2

STEPS TO THE SAND - Welcome to your tranquil oasis on Siesta Key at our first floor 2 bedroom, 2 bathroom beach bungalow style cottage unit with plenty of room for family and friends. Enjoy the Siesta Key sands and famous Point of Rocks beach access just steps away. Relax in our expansive living/dinning room while watching large 60in TV's, perfect after a long day at the beach. The properties amenities boast private balconies, tiki hut, pool, hot tub, grill, and parking.

Condo in Gulf Gate Estates

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.

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.

4.96 out of 5 average rating, 157 reviews

5.0 out of 5 average rating, 109 reviews

Quiet Gulf & Canal View 1 BR -2 Supyaks-Htd Pool

💙 Rare 2-week opening for February 2027! Escape the winter together at BayDreaming, a romantic 1BR/1.5BA retreat just an 8-minute walk from Turtle Beach. Sip sunset cocktails on your private canal- and Gulf-view deck, enjoy a heated pool, paddle the included SUPYAKs, and unwind in a plush king bed. With garage parking, beach gear, and peaceful waterfront surroundings, it’s the perfect Siesta Key escape to relax, reconnect, and soak up the sunshine.

4.96 out of 5 average rating, 123 reviews

A sandy pathway leads to the beach, framed by lush greenery and tall grasses. The gentle waves of the ocean are visible in the distance, with a clear blue sky overhead. Sunlight casts a warm glow on the pathway, inviting relaxation.

Condo in Venice

Steps to Beach + Walk Dwntwn | King | Dogs | #4

Location Location Location! A few steps to beach, and short walk or bike ride down the tree lined boulevard takes you to Historic Downtown Venice where you'll find, Restaurants, Cafes, and Boutiques. Experience island life from this 1 BR, 1st floor condo, walk to everything. Pack your bathing suit, and flip flops, with all the comforts of home, beach towels, umbrella, and chairs, provided, that's all you'll need here! Sofa bed also available.

4.92 out of 5 average rating, 172 reviews

Cottage on Siesta Key Beachside & Stunning sunsets

Come experience Siesta Key and relax in our beachside cottage. It is sure to refresh you , whether you prefer an incredible one of a kind sunset or a long leisurely walk on the beach with the cool sugar white sand beneath your toes! This is an escape you deserve. The pool is beautiful and conveniently located on your stroll to the beach. If you enjoy music , we are close to several places you can sit & enjoy under the Tiki Huts with refreshments!

A serene lanai view features a dining table with chairs overlooking the community pool. Lush palm trees frame the scene, while sunlight reflects off the water's surface. A doorway is visible, leading to the interior of the condo.

4.96 out of 5 average rating, 225 reviews

Gateway to Siesta Key - 1/2 Mile to the Beach

Beautiful and comfy 2 bedroom/2 bathroom condo that sleeps 4. The condo is located only 1/2 mile from the Gulf Of Mexico. Spacious, comfortable, in a small & quiet complex that provides easy access to restaurants and stores on or off Siesta Key. You'll get super easy Siesta Key access (3 min drive/20 min walk) at a very affordable price in a perfect location to avoid traffic and enjoy the rest of Sarasota when you're not at the beach.

A bright and airy living space features a modern sofa facing a sleek coffee table. The open kitchen is visible in the background, showcasing white cabinetry and bar seating with stylish stools. Light fills the room through large windows, enhancing the spacious feel.

4.96 out of 5 average rating, 165 reviews

Modern Coastal Oasis - Beach and Private Patio

Search no more… we have it all! Enjoy this newly remodeled Siesta Key beachside retreat with a sleek modern kitchen and luxury king-sized bed. You're a 3-minute walk to private beach access and right across the street from local shops, dining, and the Siesta Key Trolley. Unwind in your private tropical patio or take a dip in the resort-style pool. With dedicated parking, you have everything needed for the ultimate getaway!

A serene beach scene captures calm waves gently lapping at the shore under a sky filled with scattered clouds. Soft hues of orange and blue reflect in the water, suggesting an approaching sunset over the tranquil coastline.

4.87 out of 5 average rating, 107 reviews

Private Beach | Gulf Views | Pool | Walk to Dining

Wake up to Gulf views, spend the day on the white quartz sand of Crescent Beach, and watch the sunset from your private balcony. Our 2-bedroom, 2-bath condo offers private beach access, a heated pool, beach chairs, umbrellas and towels, plus a fully equipped kitchen and free parking. Restaurants, bars, coffee and ice cream are within walking distance, so you can enjoy Siesta Key without spending your vacation in the car.