Vacation rentals with a patio in Ridge Wood Heights

A modern kitchen is presented with warm wooden cabinetry and stainless steel appliances. A large island provides seating with two white stools. Sunlight illuminates the space through a window above the sink, where a bouquet of flowers adds a vibrant touch.

4.99 out of 5 average rating, 128 reviews

Siesta Breeze ~ Charming Coastal Cottage

Message me for 🔥🔥 last minute deals!! 5 miles from Siesta Beach, named No 1 Beach in the US, No 4 in the World by Tripadvisor; close enough to feel the sea breeze:) You will have 2 bathrooms, 2 bedrooms with queen beds and a flex room with a futon and work area, for 3 private sleeping areas. You will be located in the heart of Sarasota, with restaurants and grocers within a mile or two. The kitchen is fully equipped and the yard fully fenced. The host is conveniently located next door.

4.98 out of 5 average rating, 142 reviews

A charming outdoor patio features a wooden pergola draped with fabric, providing shade over a seating area with four chairs. Lush greenery, including a palm tree, surrounds the cottage, nestled on a gravel area, creating a serene and inviting atmosphere.

Home in South Sarasota

The Mango House Beach Cottage

Our cozy boho beach cottage, The Mango House is the perfect place for a couple or small family to relax and enjoy all the best Sarasota amenities. It’s conveniently located right between both Siesta Key entrances, walking distance to restaurants, grocery stores, Trader Joe’s, gym and a block from the popular Walt’s Fish Market. This gorgeous bungalow is the front house of a duplex on a large lot with plenty of cozy private outdoor space to relax and take in all the wonderful Florida weather!

5 out of 5 average rating, 21 reviews

4BRHeated Pool•Fire Pit•Pool Table Mins Siesta Key

Welcome to Casa Trinidad — Your Coastal Oasis in Sarasota! Escape to Casa Trinidad, a bright and stylish 4-bedroom coastal retreat located just minutes from world-famous Siesta Key Beach and vibrant Downtown Sarasota. Whether you’re planning a family getaway, a couples’ trip, or a relaxing retreat with friends, this home offers everything you need for the perfect Florida stay — a heated private pool, fire pit, BBQ area, game room, and all the cozy coastal touches that make it unforgettable.

Superhost

A swing chair hangs from the ceiling in a cozy living space, complemented by a dark sectional sofa and a round coffee table. A decorative rug adds warmth to the wooden floor, while a wall-mounted television and a piece of artwork provide visual interest.

4.81 out of 5 average rating, 182 reviews

1 House 1400sq. ft. 12 min from Siesta Key!

12 min. from Siesta Key Beach!! Perfect cozy vacation home in quiet, friendly neighborhood. Central to lots of shopping/restaurants. 1-king, 1-queen, bunk beds w/ 1-full & 1-twin. Dog & cat friendly w/ large private fenced yard, & 1-men's & 1-women's bike. Air hockey table w/ board games & pool toys. Fully loaded kitchen & W/D. Spacious living w/ large sectional, swing chair, & all bedrooms come w/ TVs & free Netflix & Hulu. Looking forward to hosting you! Message me anytime w/ questions.

A serene evening view of a swimming pool surrounded by lush landscaping. Illuminated by soft lights, the pool area features umbrellas and comfortable lounge chairs. In the background, trees and a gazebo create a tranquil atmosphere, enhancing outdoor relaxation.

4.82 out of 5 average rating, 17 reviews

Siesta Shores II

Upscale pool house close to Siesta Key and downtown on a private street. This house is designed to meet highest traveler's expectations. Fully remodeled to have the ultimate experience. But all the details inside will not beat the pool area that has been added in 2024! Also we recently added ledge loungers and pool umbrellas, a gazebo with string lights, fire table and lounger, pool and back yard illumination, plenty of landscaping for privacy and fresh lawn. Wait for our new aerial pics.

A spacious bedroom features a light-colored bed adorned with neutral bedding. A cozy chair is positioned nearby, complemented by a decorative area rug. Natural light streams through large windows, and a brick wall hosts a television above a decorative fireplace.

5 out of 5 average rating, 31 reviews

Little Creek Retreat/4.5 mi to the Beach!

Find your peace and quiet right in the heart of Sarasota. Spacious farmhouse on an acre of old Florida land, decorated with palms, oaks, giant philodendrons, colorful crotons and Korean hibiscus bushes. Wake up with birds, walk with butterflies along the quiet creek, fall asleep with the sounds of crickets. Enjoy a full body and mind recharge with the conveniences of the vibrant downtown Sarasota in your arm's reach and just moments away from the world-renowned Siesta Key Beach!

A fenced backyard showcases a heated pool surrounded by landscaped areas. Lounge chairs are positioned beside the pool, inviting relaxation. Sunlight reflects off the water, while a screened lanai provides a shaded space for enjoyment.

5 out of 5 average rating, 33 reviews

Renovated charmer w/ heated pool

Your family will be close to everything when you stay at this centrally-located place - 2 miles from Siesta Key Beach and 3 miles from downtown Sarasota. The house is fully renovated and the property enclosed with 8ft fence ensuring complete privacy. The spacious landscaped backyard with screened lanai and heated pool provides for a perfectly enjoyable and relaxing time. The 2 bedroom, 2 bathroom home is elegantly yet practically appointed for a comfortable stay for 4 people.

Home in Gulf Gate Estates

4.97 out of 5 average rating, 125 reviews

Relax+ Jacuzzi | 9 Min to Siesta Key Beach

Important for privacy-conscious guests: You are renting a fully private home. There are no shared spaces of any kind. Stylish 4BR home 9 minutes from Siesta Key. Private jacuzzi, equipped kitchen, fast Wi-Fi, and outdoor grill. Sleeps 8, 2 bathrooms. Pet-friendly with fee. Please note: A separate structure on the property has its own entrance and does not share space with the guest home.

4.98 out of 5 average rating, 121 reviews

Your DreamOasisAwaits: SiestaKeyEscape with Pool!

Welcome to your dream oasis near the world-famous Siesta Key! ✨ This immaculate 2BD/2BA home is a true coastal gem, offering a serene retreat with stylish design and luxurious amenities. Just 1 mile from the sugar-white sands of Siesta Key Beach, this home provides the perfect blend of comfort and convenience—an ideal spot to embrace relaxed Florida living at its finest. 🌴

5 out of 5 average rating, 23 reviews

Sarasota Summer House

New House, experienced host! - Bright and spacious 3-bedroom home with soaring ceilings, an open-concept kitchen, and natural light pouring in from every angle. Step outside to your private backyard oasis complete with a sparkling pool, outdoor shower,tropical landscaping, and space to lounge or play. The perfect spot to relax, recharge, and enjoy the sunshine.Maximum 2 pets

Superhost

4.85 out of 5 average rating, 26 reviews

Serene Blue House

Enjoy amazing days in a cozy home in Sarasota in the State of Florida. With lovely rooms, an ocean-inspired art painting on the walls, and accommodations up to 6 people, this is your entryway to paradise near breathtaking beaches with crystal clear waters and white sand like the worldly famous Siesta Key Beach only 10 min away. Book now and enjoy unforgettable days.