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,

Superhost

A spacious bed with a white coverlet is flanked by two nightstands featuring soft lighting. Decorative pillows rest atop the bed, and a tasteful piece of wall art adds a touch of color to the neutral backdrop.

Apartment in Sarasota

4.85 out of 5 average rating, 247 reviews

Updated Old Florida Studio Getaway in Central SRQ

This apt is a breath of fresh air- you'll feel it when you enter and immediately feel calm and at peace. Sparkling clean & spacious with a king-sized, comfortable bed, a full bathroom and kitchenette, & special old Florida style decor gives you the sense of southern hospitality that you're looking for. Central to much of Sarasota, you can be from here to the island of Siesta Key in less than 10 minutes! Whether you're here for business or pleasure, this sweet studio is sure to be a highlight.

4.98 out of 5 average rating, 129 reviews

Condo in Sarasota

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.

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, 183 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.

4.95 out of 5 average rating, 418 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)

5 out of 5 average rating, 112 reviews

Home in Arlington Park

The Blessing House- Htd Pool/Spa, Close to Beaches

Welcome to The Blessing House, a beautifully curated Sarasota retreat designed for relaxation, comfort, inspiration, and quality time together. Enjoy a heated pool & spa, lush lanai, bright designer interiors, and a peaceful residential setting just 15 minutes from Siesta Key, Lido Key, and downtown Sarasota. Thoughtfully maintained and enjoyed by our family throughout the year, this home is ideal for couples, families, and discerning travelers seeking a restful and memorable getaway.

The kitchen area features a white cabinetry design with open shelving. A round dining table is set for four with a grey tablecloth. Modern appliances, including a stainless steel refrigerator and a mixer stand, are visible along with a sleek, well-lit countertop.

4.96 out of 5 average rating, 231 reviews

Adorable Bungalow Fire pit/outdoor shower 2/1 Cute

Charming and tranquil two bedroom home located in central Sarasota. This adorable bungalow is just 6 miles from world famous Siesta Key Beach. Located on a quiet street you are just minutes from great restaurants and shopping. The house is an adorable bungalow with a sweet cottage feel inside. The backyard is private with a fence all around. You can enjoy laying in the hammock and by night sit around the fire pit. There is an outdoor shower with cold and hot water to enjoy.

4.92 out of 5 average rating, 363 reviews

A private caged pool area is surrounded by lush tropical greenery. A turquoise umbrella provides shade over a lounge chair, while a series of blue-tiled steps lead into the pool. Potted roses add a touch of color beside the water.

Guest suite in Sarasota

Beach & Town Posh Location! Jungle Paradise Studio

PRIME! To Town&Beach Locations! *Private Studio* *NO Smoking *NO Children. *Shared Pool. Studio w/private entrance & patio @Designers private Home,Tropical Jungle, like Posh Resort! Quiet, residential area. Sought-after amenities. 10 min/Siesta Beach, shops, dining, & 5mins/Downtown Sarasota. Walk/local markets/ dining/movies & shopping New King bed. New 50" TV. Off street parking. No Smoking/Vaping! No kitchen. No Hotels in my exclusive area! Live like a local!

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.

4.95 out of 5 average rating, 145 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-Heated Private 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 & snowbirds to enjoy Florida living!

4.98 out of 5 average rating, 122 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. 🌴