Holiday rentals with outdoor seating in Sarasota

A wide view of a sandy beach features clusters of beachgoers enjoying the sun. Colorful beach chairs and umbrellas are scattered across the white sand. The gentle waves of the blue ocean can be seen in the distance, with high-rise buildings lining the shore.

4.95 out of 5 average rating, 290 reviews

2 Miles to Siesta Key

Excellent Location. Private & Quiet - Private Entrance & Quiet Surroundings - Comfortable Bedroom & Bath with King Bed - Small Kitchenette fridge/freezer/microwave/coffee maker Private entrance to Guest Suite with full bathroom, kitchenette, sink and countertop, fridge and freezer, microwave, and coffee maker. This provides ample utility to prepare simple meals, but it is not suited for cooking. Located in Gulf Gate with over 150 shops including bakeries, coffee shops, restaurants and more..

The kitchen features modern white cabinetry and appliances, complemented by a stylish wood tabletop with two stools. A large window provides natural light, while a beach-themed artwork adds a calming touch. The space is designed for functionality and comfort.

4.76 out of 5 average rating, 191 reviews

Private apartment w/King bed+full kitchen

Welcome to our newly renovated apartment with King size bed and full kitchen. Parking in the driveway and self check in process make this is a safe and convenient stay whether you’re traveling solo or as a couple. Located on a quiet street yet close to the main road and access to the Legacy Trail + Pompano pickle ball courts at the end of our street. 5 minutes to Pinecraft, local ice cream, restaurants & approximately 7 miles to Siesta Key and Lido Key Beach and 15 minutes to Sarasota airport.

A spacious king bed is centered in the room, dressed with soft gray linens and a decorative throw. Two bedside tables with lamps are positioned on either side, and wall art featuring tropical foliage is displayed above the bed. A neon sign adds a modern touch.

4.9 out of 5 average rating, 214 reviews

Private fenced yard, BEACH GEAR, and king bed!

This King studio sleeps two and Includes a private fenced outside area with EVERYTHING you need for the beach! It also features Netflix, HBO Plus, Disney+, Hulu, and Amazon. Within a mile you have everything you need! Grocery, CVS pharmacy, great dinning, Evie's mini golf & driving range, and more. Located off Bee Ridge within 10 miles from Siesta beaches, St. Armands Circle Shopping, Lido Beaches, Downtown, Moet Aquarium, Kayaking Mangroves, Big Cat Habitat, Sky Zone, Rental boats, and more!

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.

4.99 out of 5 average rating, 216 reviews

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!

4.99 out of 5 average rating, 260 reviews

A private stock tank pool is surrounded by a wooden deck and lounge chairs. An umbrella provides shade over the pool area. Colorful towels and a stylish table with refreshments are visible, set amidst a landscaped courtyard with lush greenery.

Guest house in Sarasota

Magical Guesthouse 1 mi from SRQ airport

@Aloe_Stranger Dreamy + fresh! This 1-bedroom guesthouse has a king bed, full bath, kitchen, washer/dryer, daybed + sleeper sofa. NEW STOCK TANK POOL! Full of style - it feels like you're in your own art installation. 1 mile from SRQ Airport, it boasts a great location as well cushy comforts. 1/2 mile from Sarasota Bay, 15 min from Lido Beach, 15 min from Siesta Key and many beaches around the Sarasota/Bradenton area. 10 min from downtown Sarasota, 1 mile from the historic Ringling Museum

4.95 out of 5 average rating, 126 reviews

Guest house in Sarasota

Downtown Garden Studio close to everything

Welcome to my brand new guest house! The original building has been rebuilt and completed in December 2024 to offer a more comfortable experience for my guests. Peaceful and centrally located, ideal for relaxation and easy access to explore historic Sarasota and the beaches. A quick drive, bike or a short walk to downtown Sarasota, Selby Botanical Garden and Pineapple Street antique shops. 1.5 miles to Sarasota Bay. 3.5 miles to St Armands Circle and Lido Beach. 6.5 miles to Siesta Key.

4.93 out of 5 average rating, 269 reviews

MG Tropical Stay. Fully private, no shared spaces

Welcome to your modern Sarasota Guest Suite – Adults Only, Private & Peaceful 🌞 Remodeled on January 26, 2026, this private suite offers a separate entrance and parking for two cars. Enjoy a cozy queen bed, full bathroom, and a kitchenette with microwave, mini‑fridge, coffee maker, and more. Relax on your private patio with a solar shower. Stay cool with a quiet mini‑split A/C. We provide beach essentials: umbrella, chairs, cooler, and towels—perfect for your Sarasota beach days 🌴

4.92 out of 5 average rating, 274 reviews

A welcoming entryway features a bright door with a small window and a decorative hanging piece. Light-colored walls surround a cozy seating area with a modern sofa. A simple side table holds a lamp, and framed artwork decorates the walls, complemented by indoor plants.

Home in Gillespie Park

*Downtown home 10min. drive to beach; walk DT*

In the heart of Gillespie Park, this bright & spacious home is a 10 min. drive to Lido Beaches and within walking distance to downtown shops, grocery, farmer's market, opera house, restaurants, bars, live music, tennis, parks, antique shops and performing arts. Old Florida bungalow on the outside, inside, it's updated with new appliances and bathrooms. A banyan tree offers private, shady repose on the back deck w/grill and dining area. Message me for room availability.

Guest house in Laurel Park

A private outdoor area features a cozy swing sofa under a wooden pergola, surrounded by lush greenery. Several comfortable chairs are positioned around a small fire pit, creating a welcoming space for relaxation. Natural light filters gently through the surrounding trees.

4.88 out of 5 average rating, 144 reviews

City Garden Cottage

City Garden Cottage is a cozy and comfortable cottage located in the quiet Laurel Park neighborhood in Sarasota, only a few blocks from downtown. The studio is surrounded by lush gardens and trees with a Hot Tub. Inside, you will find a kitchenette equipped with a coffee maker, toaster, refrigerator, and hot plate. The studio also has a flat-screen TV, a queen bed & private bathroom. There is also shared use a gas grill, fire pit and Hot Tub included with the rental.

4.98 out of 5 average rating, 107 reviews

The living area features a comfortable seating arrangement with a light-colored sofa and two armchairs, adorned with decorative pillows. A stone fireplace is centered against a wall, complemented by wood beams overhead. Natural light filters through sheer curtains, creating a cozy ambiance.

Guest house in Sarasota

The Cottage (In the Country) Cozy, Quiet Retreat

Relax, unwind and unplug at this cozy Old Florida-style country cottage! Here you are away from it all in peaceful bliss... but if you want to go out for dinner, it's an easy drive into town! Located on a beautiful 5 acre plot, this guest home is the perfect spot for your Florida getaway! Just 30 minutes from Siesta Key and 6 minutes from the entrance to Myakka State Park, you can see the best of Florida, both the swamps and the beaches, all in one day!

4.97 out of 5 average rating, 196 reviews

A studio apartment features a king bed against a light wall, complemented by a cozy seating area with a gray sofa and a chair nearby. Two round coffee tables sit on a neutral rug, with a wall-mounted smart TV and built-in shelves adding practical style.

Flat in Arlington Park

Studio Minutes to Siesta key, Lido Key, and SMH!

Enjoy sunny Sarasota, FL in our studio apartment. Located between Siesta Key and Lido Key. You can walk to Southside Village, Sarasota Memorial Hospital (SMH) and Arlington Park. Enjoy the beautiful neighborhood and easy access to Legacy Trail. Approximate driving times to popular local destinations: Siesta Key - 10 minutes Lido Key - 14 minutes SRQ airport - 15 minutes St Armands - 10 minutes Downtown - 7 minutes

Home in Indian Beach-Sapphire Shores

A light-filled living area features a sleek black sofa adorned with green cushions, paired with a glass coffee table. A colorful bookshelf is positioned against one wall, while large windows with unobstructed views invite natural light and views of the surrounding greenery.

4.99 out of 5 average rating, 100 reviews

Magical Secluded Retreat

Light-filled mid-century gem, newly renovated with cathedral ceilings. A lush canopy of tropical plants and trees offers privacy and calm unusual for its central location in Sarasota's historic neighborhood on the Bay. Relax inside and out, and lose yourself in birdsong, gently swaying bamboo and beautiful nature. Just 10 minutes to world-renowned beaches and even closer to dining, shopping and museums.

Popular amenities for outdoor seating rentals in Sarasota

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

House rentals with outdoor seating

A private backyard is illuminated with string lights in the evening. A fire pit table with a glass barrier features dancing flames, while a hammock is visible to the side. The space includes lounge seating with turquoise cushions, creating a relaxed outdoor atmosphere.

4.91 out of 5 average rating, 169 reviews

Quiet Retreat-5mi to Beach-Hot Tub, Outdoor Shower

An open living area is presented, featuring a blue couch and a wooden coffee table. A dining table with four chairs sits nearby, complemented by a kitchen with white cabinetry and modern appliances. A Christmas tree adds a seasonal touch, while windows allow natural light.

4.96 out of 5 average rating, 105 reviews

2 BR House 1.6 miles from Siesta Key Beach

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.

4.88 out of 5 average rating, 121 reviews

Charming Villa 14 mins away from Siesta Key Beach

A bright pink flamingo float adorns the clear, inviting waters of the heated pool. Two white umbrellas provide shade for the striped lounge chairs nearby. Flower pots add a touch of greenery to the poolside area, which is enclosed by a white privacy fence.

4.94 out of 5 average rating, 115 reviews

Oasis by Siesta Key Beach and Downtown SRQ w/pool

A modern kitchen features dark wood cabinetry and a granite countertop. Stainless steel appliances, including a refrigerator and dishwasher, are included. A doorway leads to a bright living area where natural light filters through a window, illuminating a cozy seating arrangement.

4.95 out of 5 average rating, 266 reviews

The Key Lime Cottage 2 miles from Siesta Key Beach

Home in Indian Beach-Sapphire Shores

A welcoming living room features a comfortable gray sofa adorned with patterned cushions. A coffee table centers the room, accompanied by a flat-screen TV mounted on a light metal stand. Natural light fills the space through a large window, highlighting the hardwood floor.

4.83 out of 5 average rating, 240 reviews

2/1 Ringling Townhome- 1.5 miles to Downtown SRQ!

4.96 out of 5 average rating, 146 reviews

A sparkling pool is surrounded by a spacious patio, featuring lounge chairs and a vibrant red umbrella. Lush tropical landscaping creates a serene retreat, providing an inviting space for relaxation and leisure under a clear blue sky dotted with fluffy white clouds.

Home in Arlington Park

Mid-Century Oasis with Pool in Arlington Park 1

The exterior of the duplex presents a welcoming entrance with a covered front porch and seating. Lush greenery and small potted plants enhance the home's facade. The driveway is visible, leading to the well-maintained lawn and fenced backyard area.

4.95 out of 5 average rating, 110 reviews

1 Bed 1 bath 7 mins to the beach

Apartment rentals with outdoor seating

A bright living area is viewed, showcasing a cozy sofa adorned with decorative pillows. Light drapes frame large glass doors that open to a vibrant garden patio. Two comfortable chairs and a wooden table complement the space, creating a welcoming atmosphere for relaxation.

4.98 out of 5 average rating, 183 reviews

Near Siesta Key Beaches - Quiet 1 BR apt

A spacious bedroom features a king-sized bed with a white bedspread and coordinating pillows. Two windows allow natural light to brighten the room, while a fan circulates air. A dark, modern couch and built-in shelves provide additional functionality and style.

4.8 out of 5 average rating, 157 reviews

Old Florida-Style Spacious Studio w/ Full Kitchen

4.97 out of 5 average rating, 180 reviews

A private entrance is framed by a sleek plant and modern features. The entrance door is flanked by a wall light and a smooth concrete pathway, complemented by potted plants that enhance the outdoor space.

Flat in Gillespie Park

Gillespie On The Park, Walk to Downtown

4.91 out of 5 average rating, 189 reviews

A comfortable sleeping area features a queen size bed dressed in white linens and patterned pillows. A decorative bench at the foot complements the dark blue headboard. Nightstands with lamps are positioned on each side, and artwork depicting coastal scenery adorns the wall.

Flat in Bradenton

Ocean Blue adorable new studio !

Flat in Indian Beach-Sapphire Shores

The enclosed pool area is surrounded by lush greenery and tropical plants, with vibrant purple lighting creating a serene ambiance. A spacious swimming pool reflects the colors overhead, while a decorative wall clock adds a charming touch. Comfortable seating is present along the edges.

4.96 out of 5 average rating, 177 reviews

ROYS PLACE Romantic, Private, Paradise!

4.97 out of 5 average rating, 235 reviews

A compact sleeping area is furnished with a wooden bed frame and a colorful assortment of throw pillows. A modern air conditioning unit is mounted above, while a bedside table holds a lamp. Light streams in through the window adorned with wooden blinds.

Flat in Bayou Oaks

Modern Private Apartment 1 Block from Sarasota Bay

4.97 out of 5 average rating, 430 reviews

A serene view of the Manatee River showcases calm waters reflecting the sky. Lush greenery surrounds the area, accompanied by a covered dock nearby. An American flag flutters gently, and a hint of a charming structure with a porch is visible to the right.

Flat in Ellenton

Serenity on the Manatee

A living room area is shown, featuring a light-colored couch positioned beneath two large windows. Natural light filters in, highlighting a small potted plant on a coffee table topped with a woven textile. A lamp and a dark wood side table are also present, adding to the room's ambiance.

4.96 out of 5 average rating, 157 reviews

★1 BLOCK TO SIESTA DRIVE★KING BED★FULL KITCHEN★

Apartment rentals with outdoor seating

4.83 out of 5 average rating, 259 reviews

A living area features a comfortable green sofa complemented by a lamp casting a warm glow. A white wicker chair adds a coastal touch, positioned beside a small white table. Light wooden floors extend across the space, with soft wall art and a wall-mounted TV enhancing the environment.

Apartment in Siesta Key

Cozy 1BR Beach Condo on Siesta Key!

4.92 out of 5 average rating, 148 reviews

An aerial view of the Sea Shell condominium displays a four-story building with balconies facing the ocean. The bright blue sky and ocean can be seen beyond the structure, emphasizing the inviting coastal location.

Apartment in Siesta Key

Sea Shell Ocean View On Beach Walk Everywhere Pool

4.94 out of 5 average rating, 160 reviews

A serene community pool is surrounded by a fence and complemented by lounge chairs positioned nearby. The pool's clear blue water reflects the sunlight, while the yellow exterior of the building provides a warm backdrop. Windows with awnings complete the inviting atmosphere of the area.

Apartment in Sarasota

Villa Maria: Minutes to Siesta Key!

4.9 out of 5 average rating, 134 reviews

A modern dining area is highlighted by a marble table with an elegant vase and tableware arranged for a meal. Stainless steel appliances and a large television are visible in the background, with natural light flowing in from sliding glass doors leading to an outdoor space.

Apartment in Siesta Key

Crystal House on Siesta Key Beach

4.81 out of 5 average rating, 124 reviews

Apartment in Sarasota

Spacious 2BR/2BA Garden Condo w/ Heated Pool

4.92 out of 5 average rating, 130 reviews

A stylish living room is presented, featuring a comfortable gray sofa paired with a decorative round coffee table. Brightly colored wallpaper adorned with shell patterns enhances the space, while large windows allow natural light to filter in, complemented by light-colored flooring.

Apartment in Bradenton

Mins to AMI | Walk to Beach & Bay

Apartment in Bradenton Beach

A spacious living area features a blue sofa and striped armchair, complemented by a wooden coffee table. Large windows allow natural light to illuminate the room, showcasing views of the turquoise Gulf. Light-colored cabinetry and decorative shelving enhance the inviting atmosphere.

4.99 out of 5 average rating, 163 reviews

★Right on the beach ★ Relax and Enjoy ♥ Sunsets!