Family-friendly holiday rentals 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.

Flat in Sarasota

4.85 out of 5 average rating, 243 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.

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, 125 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, 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!

4.88 out of 5 average rating, 265 reviews

Tiny home in Sarasota

@Tiffanythetinyhome| island | netflix|bike|hammock

You are about to book a famous HGTV 270ft² / 25m² tiny home on a private 1.5-acre island! ☆ Walk to dining, nightlife, and shopping ☆ Fully equipped kitchen (K-cup) ☆ Backyard fire pit + BBQ ☆ Screened-in outdoor lounge w/ hammocks ☆ 415Mbps ☆ Smart TV w/ Netflix ☆ Memory foam bed ☆ FREE Bikes + kayaks + beach gear 3 min → Siesta Key Beach 7 min → Downtown SRQ 12 min → Myakka River State Park (river kayaking + wildlife viewing) We use a compost toilet. Please read house rules for info.

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, 139 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 vibrant blue exterior of the home is highlighted by white trim and large windows. The entrance features a wooden deck with a small step, while surrounding landscaping includes gravel and small plants. Mature trees provide shade in the front yard.

4.93 out of 5 average rating, 141 reviews

Papi's House - 5 miles to Siesta Key & Downtown

This newly remodeled 2 bed, 2 bath home is centrally located in Sarasota. With plenty of space to spread out, beautiful natural light that pours into every room and a private fenced-in yard, this is the perfect place to relax. This home is located in a quiet neighborhood and just 5 miles away from the #1 rated Siesta Key Beach and downtown Sarasota. It offers plenty of driveway parking. Beach chairs and a cooler are provided for your days at the beach. Fast WIFI is also available.

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!

4.97 out of 5 average rating, 464 reviews

Guest suite in Sarasota

Adorable studio close to Siesta beach!

Come stay in this private studio with its own fenced in patio in the back! Has shared washer and dryer. New Queen bed ,pullout couch (twin). gas grill,toaster oven/airfryer, microwave , hot plate for cooking and full fridge plus ac unit. Rainfall showerhead and river stones on shower floor. beach chairs ,towels available. Off street parking in driveway. The famous, huge fresh market " Detweilers" is only 1.5 miles away

4.98 out of 5 average rating, 118 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. 🌴

Apartment in Gulf Gate Estates

A cozy living area features a blue sectional sofa accompanied by decorative pillows and a side table with a lamp. A wall clock adds a modern touch, while large sliding glass doors offer views of the outdoor space. A dark blue accent chair complements the scene.

4.89 out of 5 average rating, 189 reviews

Lake View 1BR Condo | Heated Pool Near Siesta

Bright 1-bedroom condo with peaceful lake views in a quiet residential area of Sarasota. Siesta Key Beach is a 5–10 minute drive (traffic dependent). Pet-friendly home — all pets welcome with a flat $10 pet fee per reservation, regardless of the number of pets. Guests enjoy access to a heated community pool and a calm setting close to shopping and dining.

A screened lanai features a bubbling hot tub and comfortable seating area adorned with neutral-colored cushions. Soft lighting is offered by overhead string lights. Surrounding greenery enhances the peaceful ambiance, while large windows allow natural light to flow into the space.