Holiday rentals with outdoor seating in Gulf Gate Estates

One of Florida's BEST! On Venice Island near BEACH

Perfectly located in a quiet friendly area with groceries, shopping and dining are blocks away. Across the street is the Venitian waterway trail that connects to the Legacy trail. Bike, walk, run this award winning trail. Venice beach 1.9 Miles, Casperson Beach 3.6 world renowned for great shark tooth hunting. Downtown Venice 1.2 Miles filled with restaurants, shops, boutiques, specialty items, stores, parks, entertainment and events. Benches and beautiful park to absorb the culture and vibe.

Gertrude's Siesta | Patio & 1-min to Beach/Village

The Village Studio Top location on island! Apartment with full kitchen, private patio, gated courtyard, in world famous Siesta Village! Leave the car behind and walk to white-sand beaches, 20 bars and restaurants, ice-cream, shopping, daiquiris, live music, craft beer, fresh oysters and seafood. Experience a combination of fun ease and relaxation you can't get in other vacations! Book a special getaway now! - Tollbooth by AirbnbCorpMiddlemen, but this property is from GertrudeRentalsSiesta

☀ Villa & Garden in Downtown ~ 5 Min to Beaches

Our coastal chic, contemporary Sun Villa is situated in Sarasota’s charming downtown historic neighborhood of Laurel Park. The villa's garden hideaway is a real Floridian oasis, complete with fire pit and sun loungers. Downtown and all its restaurants, bars and shops is just on your doorstep. Plus 3 sugar white beaches – including Siesta Beach one of the most beautiful beaches in the world – are only a 5-min ride away! We’ve poured our hearts & souls into this villa, it's our family business.

Heated Pool Oasis 3BR/2BA near Siesta Key Beach

Relax at this modern heated pool house located just 15 min from the famous Siesta Key Beach. Nested in a quiet neighborhood with a lot of privacy, the house has plenty of space for an entire family or a group of friends. An additional family room with a TV for kids. Relax by the pool in the spacious outdoor area or explore the beautiful downtown filled with restaurants. Recently renovated, this home offers handmade authentic Mexican tile flooring to compliment a cozy and contemporary design.

The Bradford Cottage/Heated Pool /Mins to Siesta

If you are looking for a cozy retreat in a safe and private neighborhood than look no further! From the minute you step inside this immaculate private residence you will feel right at home. With a beautiful open floor plan with plenty of room to spread out, natural light that pours in every room and a spacious back porch overlooking the heated pool this is the perfect place to unwind and relax. Minutes from the #1 rated Siesta Key beach and downtown Sarasota you are in the middle of it all!

Sunshine Awaits- Heated Pool Home! 6 min to DWTN!

Escape to your own private Sarasota oasis! This 3-bed, 2-bath vacation home boasts a heated pool for sun-soaked days & unforgettable evenings under the stars. Find a fully-equipped kitchen, comfy living space, Smart TVs, & free WiFi. Included are a gas grill & board games for poolside BBQs & family fun. Close to local shops, restaurants, & parks. World-famous Siesta Key Beach & Lido Beach are a short 15 min away, along with a 10 min drive to vibrant downtown Sarasota & its cultural scene.

Cute Little Getaway

Close to the beach and walking distance to 5 restaurants, including one on the water. Our place is less than 2 miles from Nokomis Beach! We have you covered on beach equipment, wagon, chairs, towels and umbrella. The backyard boasts a relaxing, beautiful escape with resort style touches. We have a gas grill to cook your catch, a high powered outdoor fan, and comfy seating in the shade. The house is freshly modernized, open and airy. You will enjoy an outfitted kitchen.

Peace in Palmetto

A spacious 2/1 home in a peaceful setting amongst large mossy oak trees. Full kitchen, 3 smart TV’s , 2 queen beds, Coffee/Tea bar, private fenced patio & sitting area with grill. Also available on premises: full size washer & dryer, boat & RV parking. Near by: Felts Audubon, world class fishing & boating, upscale outlet mall, stores, restaurants, pubs & breweries. Centrally located to award winning beaches, theme parks, & 3 airports: Tampa, St Pete, and Sarasota.

Sunny Vida - Heated Salt Pool & Separate Chic Loft

Escape to a serene retreat in the heart of Sarasota, FL, where modern design meets tranquility. This stylish 3 bedroom 2 bathroom sanctuary is ideal for travelers seeking a peaceful haven in Sarasota. Take advantage of our comfortable and newly renovated private unit separated from the main house. Step outside to the private patio or take a leisurely stroll downtown to cafes, restaurants, and attractions, immersing yourself in the vibrant local culture.