Holiday rentals with outdoor seating in Ridge Wood Heights

An open concept living area is captured, featuring a wooden coffee table centered between a light-colored sofa and loveseat. A blue bookshelf holds decorative items. A television is mounted on the wall, while the dining area is subtly visible in the background.

4.97 out of 5 average rating, 146 reviews

Near Siesta Key| Pet Friendly Sarasota Retreat.

Escape to this beach inspired bungalow with a fully equipped kitchen and a fenced yard to relax in the sunny outdoors. Only 10 minutes to Siesta Key Beach! Enjoy the Sarasota beaches, museums, parks and downtown Sarasota, all just minutes away. Centrally located to grocery stores and restaurants. From coastal decor to comfortable beds, every part of your experience was thoughtfully curated by the owners to allow you to sit back, so feel free to put your feet up and relax at Barefoot Bungalow,

4.99 out of 5 average rating, 235 reviews

A covered patio space is surrounded by lush greenery and decorative plants. A light-colored table and two chairs are arranged on a tiled floor. Large, double doors in a vibrant blue lead to the outdoors, enhancing the welcoming atmosphere.

Guest suite in Sarasota

Mid-Century Modern Beach Getaway

Heart of Southside Village 10 minutes from #1 beach in the USA, Siesta Key. Five-minute drive to downtown Sarasota, 10 minutes to St. Armand Circle, Lido & Longboat Key. Enjoy this peaceful space within walking distance to shopping, restaurants & groceries. Charming private guest house offers a queen bed, sitting chairs, table, dresser, large ensuite bathroom with a walk-in shower & private outdoor sunny space and patio. Use the grill to cook your next meal. It's the perfect couple's getaway!

4.98 out of 5 average rating, 139 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!

4.95 out of 5 average rating, 415 reviews

Tiny home in Sarasota

@Shellmateisland |tiny home| island| bikes| kayaks

⭑Octagonal 320ft² tiny home sitting on a private 1.5-acre island!⭑ ✯ Lake access ✯ Walk to dining, nightlife, and shopping ✯ Fully equipped + stocked kitchen ✯ Free bikes + kayaks +beach gear ✯ Backyard fire pit + BBQ ✯ Screened-in outdoor lounge w/ hammocks ✯ Smart TV w/ Netflix ✯ Memory foam bed ✯ 426Mbps wifi Ask which fruit trees are in season for a homegrown treat! 3 min → Siesta Key Beach 7 min → Downtown SRQ 12 min → Myakka River State Park (river kayaking + wildlife viewing)

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, 138 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 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, 32 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.

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.

4.96 out of 5 average rating, 138 reviews

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.

The outdoor area features a heated pool surrounded by a serene landscape of palm trees and decorative stones. An adjacent BBQ grill offers outdoor cooking options, while comfortable seating is available nearby. The patio area is partially shaded by a pergola, providing a relaxing space.

4.96 out of 5 average rating, 226 reviews

The Oasis-Private Heated Pool Hot Tub-5mi to beach

"The Oasis" is a renovated beach cottage with heated private pool & hot tub in the heart of Sarasota. It's 5 miles to the #1 beach in the USA: Siesta Key Beach. The cottage offers 2 bedroom & 2 bathrooms, and a bonus room that can be used to sleep 6 comfortably. The one-of-a-kind fully private, fully enclosed backyard includes heated pool, hot tub, BBQ grill, outdoor dining table & fire pit for families and snowbirds to enjoy Florida living!

4.94 out of 5 average rating, 86 reviews

The exterior of a midcentury waterfront home is showcased, featuring a smooth driveway leading to a modern facade accented with orange and white. Lush greenery surrounds the property, including palm trees and manicured lawn areas, under a bright sky with scattered clouds.

Home in South Sarasota

Waterfront Home by Ralph Twitchell

Beautiful midcentury waterfront home on Phillipi Creek close to all that Sarasota has to offer. 5 miles to America's number 1 beach Siesta Key, and only a few short blocks from stores, nightlife, & other beaches. This quaint getaway includes a kayak to enjoy the pure bliss of the calm waters of Phillipi Creek as well as a game room including a pool table, foosball table, and a fireplace to lounge around and chat.

4.98 out of 5 average rating, 117 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. 🌴