Vacation rentals with outdoor seating in South Sarasota

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.

4.89 out of 5 average rating, 136 reviews

Crystal House on Siesta Key Beach

This is an updated and renovated two bedroom suite on Siesta Key. Complete with marble dining table, stainless appliances and large televisions. There is a computer in the spare bedroom for your convenience along with an Xbox and DVD player. We tried to think of everything so please feel free to make suggestions after your stay. Your satisfaction is our number one concern. The sofa is a Laz-Y-Boy and is not a sleeper but is very comfortable!!! There is a set of twin-twin bunks in the main room!

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.

4.99 out of 5 average rating, 122 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, 532 reviews

A living area features wooden flooring with a large area rug at the center. Two gray armchairs are positioned near a media console, which supports a flat-screen television. Natural light is provided by windows adorned with sheer white curtains, and a green plant adds a touch of greenery.

Home in Arlington Park

The Cottage At Central Park

There is no more charming place to stay! From the minute you step inside this immaculate and cozy private residence you will feel right at home. With a beautiful open kitchen, natural light that pours into every room, a spacious back porch overlooking the pool and fenced in yard with a fire pit, this is the perfect place to entertain AND relax. Minutes from the #1 rated Siesta Key beach and downtown Sarasota in one of the areas most sought after neighborhoods you are in the middle of it all!

4.89 out of 5 average rating, 162 reviews

A cozy sleeping area features a queen-sized bed dressed in a vibrant teal comforter, complemented by matching pillows. A soft throw pillow with 'fun times' text sits in the center. Soft lighting is provided by wall-mounted sconces above the bed.

Guest suite in Sarasota

Daydreams of Siesta Key,Private Guesthouse in SRQ

Welcome to Daydreams Siesta key, where vacationing will be a pleasure. A cozy place just 3.8 miles from Downtown Sarasota. We have the most beautiful beach in the world “”Siesta key”” at only 4 miles, we have Lido Beach at 5.1 miles which are the closest to our home. Further north is Longboat Key Beach at 10 miles . If you want to take a boat ride and take the excursions and dine on the water's edge, you can visit the Marina Jack 4 miles away. We encourage you to visit St. Armands., too.

Cottage in Indian Beach-Sapphire Shores

The cottage features a welcoming exterior with a screened-in lanai, framed by decorative beams and charming window boxes. Lush greenery surrounds the property, and a large tree adds to the tranquil setting. A pathway leads to the front door, enhancing the inviting atmosphere.

4.8 out of 5 average rating, 280 reviews

Cozy Cottage by the Bay

Charming and historic decorator cottage near Downtown Sarasota. Located in the highly desirable, quiet, and safe neighborhood of Indian Beach - Sapphire Shores. Just a short drive to some of the nations top rated beaches like Siesta Key Beach. One of the best features of the home is the enclosed lanai at the front of the house. Perfect for enjoying Florida's coveted indoor/outdoor living. It has a private fenced in backyard, with a fire pit. Off street parking for 2 cars in the driveway.

Home in Indian Beach-Sapphire Shores

A private courtyard featuring a heated pool is surrounded by lush tropical landscaping. Comfortable lounge chairs are positioned beside the pool, and a small fountain adds a soothing element. A cozy seating area is visible near the entrance to the adjoining building.

4.94 out of 5 average rating, 132 reviews

Pool Courtyard, patio w/ fire pit, 2 mls downtown

Enjoy this unique courtyard-style Spanish colonial home just steps to Sarasota Bay and 2 miles from downtown. The property consists of a 2 bed / 1 bath main house AND a detached studio. Everything pictured is yours to enjoy, nothing is shared. The houses are separated by a quaint & private pool courtyard w/ outdoor shower. Capture a photo of the local peacocks, eat fresh mangos from the yard, catch a sunset over the bay, or enjoy the sun by the pool listening to the Zen fountains.

A person is seated at the edge of a sparkling pool, facing the clear blue water. The poolside is tiled, and the sunlight reflects off the surface, creating a serene ambiance. The individual wears a swimsuit featuring a tiger stripe pattern.

4.95 out of 5 average rating, 124 reviews

Luxury Pool Family Paradise-Siesta Beach/DT-3BR/2B

Welcome to your home away from home! This renovated, spacious and bright pool home will immerse you into a luxurious experience the minute you arrive. Located on a lush quiet street, yet close to all of Sarasota's best attractions! Close to Siesta Key Beach (#1 beach in USA), 10 minutes to downtown including fantastic restaurants and shopping and walking distance to the famous Fresh Fish Waltz Market. Easy I-75 access, Nathan Benderson Recreational Lake park and The new UTC mall!

4.95 out of 5 average rating, 189 reviews

Home in Bellevue Terrace

Modern 4BR Home *Heated Pool & Spa*

Discover elegance in this centrally located Sarasota gem, featuring four bedrooms and two bathrooms to accommodate up to eight guests. Enjoy a laid-back vibe while lounging at Sarasota's beaches or immersing yourself in local attractions. Siesta Beach and Lido Beach are within easy reach at 7.6 and 6.4 miles respectively. Rest easy knowing commitment to cleanliness aligns with your travel priorities. Your serene vacation awaits in this beautifully adorned home. VR24-00265

4.92 out of 5 average rating, 353 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!

4.97 out of 5 average rating, 104 reviews

A bright living space features a large window allowing natural light to fill the room. A modern coffee table sits atop a striped rug, with a sleek TV mounted on the wall. Decor items and a welcoming door can be seen in the background.

Home in Whitfield

Lovely Home by Sarasota Bay

Enjoy a stylish coastal bungalow in North Sarasota, just minutes from downtown’s restaurants, shops, and Sarasota Bay. Relax in modern comfort with central A/C, high-speed WiFi, and smart TVs in every room. Nearby, explore beaches like Siesta Key, Lido Key, and Anna Maria Island. The fully-equipped kitchen, comfortable bedrooms, and modern bath make for a relaxing stay. Plus, you’re close to top attractions like The Ringling Museum, Marina Jack, and more!

Home in Gulf Gate Estates

A spacious backyard features a heated private pool surrounded by a paved area. Lounge chairs are positioned around the pool, with umbrellas providing shade. Lush greenery and a fence frame the yard, creating a serene outdoor setting, ideal for relaxation.

4.78 out of 5 average rating, 114 reviews

Minutes to Siesta! 4BR 2BT Heated Pool Fenced Yard

Spacious 4-bedroom, 2-bath home with a heated private pool, just minutes from the #1 Siesta Key Beach! Located in the Gulf Gate area, you’re only a short drive to the beach, grocery stores, and dining. Enjoy a fully fenced backyard, plenty of parking, and outdoor grill. Inside, you’ll find beach supplies, a fully equipped kitchen, Keurig & drip coffee makers, and TVs in every bedroom—everything you need for a comfortable and convenient stay 🌴☀️

Popular amenities for South Sarasota outdoor seating rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

House rentals with outdoor seating

4.92 out of 5 average rating, 12 reviews

Home in South Sarasota

Endless Summer | Private Pool & HOT TUB

A spacious backyard is shown at sunset, featuring a heated pool surrounded by a tiled patio. Tropical palm trees frame the area, and a tiki bar can be seen in the background. Soft outdoor lights create a welcoming ambiance as the sky fills with vibrant orange and purple hues.

4.93 out of 5 average rating, 148 reviews

The Sand Castle - Backyard Oasis Mins from Siesta!

5 out of 5 average rating, 33 reviews

An open living area features cozy seating arranged around a coffee table, with a modern electric fireplace nearby. Sunlight filters through large windows, illuminating the space. The dining area is visible in the background, showcasing a round table with comfortable seating for four.

Home in South Venice

🌺 Stunning 2 Br/2 Ba Pool Home Near Beaches

A heated saltwater pool is surrounded by a fully screened area, providing a private outdoor retreat. Colorful lounge chairs are positioned near the pool, with grass and a fenced yard visible in the background, offering a relaxed atmosphere for leisure.

4.86 out of 5 average rating, 86 reviews

Siesta Key Private Retreat -Screened Pool Haven

The exterior of the duplex presents a welcoming facade, featuring a covered entryway with a chair and potted plants. A paved driveway leads to the porch, surrounded by a grassy area. Ample natural light highlights the subtle blue sky and greenery in the background.

4.97 out of 5 average rating, 100 reviews

2 bedroom 1 bath 7 mins to the beach

4.94 out of 5 average rating, 118 reviews

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.

Home in Southgate

Oasis by Siesta Key Beach and Downtown SRQ w/pool

4.94 out of 5 average rating, 155 reviews

A screened-in pool area is showcased, featuring a heated pool with clear blue water. Sunlight casts shadows on the tiled surface, while a picturesque view of a private lake and surrounding greenery is visible in the background.

Home in Sarasota Springs

Lake Front House with a Pool

Home in Gulf Gate Estates

A spacious living area is highlighted by a modern sectional sofa adorned with colorful pillows. Decorative shelves display vibrant accents, while a round coffee table sits atop an area rug. Light flows through large windows, enhancing the open-concept layout that connects to the dining space.

5 out of 5 average rating, 22 reviews

Mid-Mod Coastal Charm - 10 mins to Siesta Key!

Apartment rentals with outdoor seating

Apartment in Indian Beach-Sapphire Shores

A spacious living area is featured with a large flat-screen television mounted on the wall. Two comfortable chairs are placed adjacent to a round ottoman, decorated with a variety of plants and a small basket. Natural light filters in through large windows, offering a view of the surrounding landscape.

4.97 out of 5 average rating, 162 reviews

Early Chkin, Elevator-4th fl 2mins-DT, 7mins-Airpt

Apartment in Gulf Gate Estates

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

4.84 out of 5 average rating, 282 reviews

A bright blue entrance door labeled 'Poolside Suite' is visible, leading into the suite. The door is framed by a light blue exterior, with a view of the pool area and palm trees in the background. Sunlight casts gentle shadows on the patio.

Apartment in Siesta Key

Siesta Key - Poolside Suite - Studio - Free kayaks

A shared pool area is surrounded by vibrant blue walls and tropical greenery. Lounge chairs in various colors are arranged around the pool, inviting relaxation. Bright sunlight reflects off the water's surface, enhancing the welcoming atmosphere of this outdoor space.

4.82 out of 5 average rating, 291 reviews

VILLA 5 · Pool view. King bed. Daily rentals

A modern living area displays a bold palm-patterned accent wall with a mounted television. Two stylish lounge chairs are positioned nearby, accompanied by a small indoor plant on a decorative table. The open layout leads to a bright and airy kitchen area.

4.92 out of 5 average rating, 130 reviews

Funky & Fun Apartment in Central SRQ

Apartment in Indian Beach-Sapphire Shores

A cozy living room features a comfortable couch with decorative orange pillows. Bright, patterned curtains complement the colorful rug and a wooden coffee table. Large windows allow natural light into the space, while a television is positioned against a cheerful yellow entertainment unit.

4.98 out of 5 average rating, 131 reviews

Come Enjoy Our Peaceful Retreat

4.84 out of 5 average rating, 113 reviews

A spacious sleeping area features a queen-size bed with a light blue patterned bedspread. A cozy armchair is positioned beside the bed, and window treatments allow natural light to brighten the room. Light wood flooring complements the neutral-toned walls.

Apartment in Lido Key

Lido Key FL Studio/Efficiency 5

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.

4.85 out of 5 average rating, 230 reviews

Updated Old Florida Studio Getaway in Central SRQ

Condo rentals with outdoor seating

Condo in Gulf Gate Estates

The living area features a light-colored sofa complemented by an orange accent chair. A coffee table sits on a textured area rug, while wall art adds color to the red accent wall. Glass doors open to a view of outdoors, surrounded by greenery.

4.91 out of 5 average rating, 138 reviews

Sunny 2nd-Floor Condo w/ Heated Pool | 1BR

A modern kitchen features white cabinetry and a spacious counter. Stainless steel appliances, including an oven and microwave, are visible. A decorative beach sign adorns the wall, and a bowl of fresh fruit sits on the counter, adding a pop of color to the bright space.

4.86 out of 5 average rating, 189 reviews

Private Beach & Intracoastal Waterfront

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.

Condo in Sarasota

Villa Maria: Minutes to Siesta Key!

A private patio with a round wooden table and two chairs overlooks a manicured lawn leading to the beach. Palm trees sway gently beside the outdoor seating area, offering a serene view of the Gulf waters in the background.

4.97 out of 5 average rating, 365 reviews

On the Beach; Siesta Key SunBum Studio

4.98 out of 5 average rating, 121 reviews

A spacious living area is highlighted by a light-colored sectional sofa adorned with colorful pillows. A large coffee table is positioned in front of the sofa, and a dining table with six chairs is visible in the background. A fan hangs from the ceiling, and natural light enters through nearby windows.

Condo in Vamo

Lovely 2-Bedroom Condo, 7 min from Siesta Beach

4.97 out of 5 average rating, 138 reviews

The bedroom features a spacious bed with decorative pillows and a light blue throw. An accent bench sits at the foot of the bed, while a round mirror reflects soft lighting from a chandelier. A patterned wallpaper adds a coastal touch, enhancing the serene ambiance.

Condo in Bradenton

KING Bed + Anna Maria Island Beaches + Beach Gear!

4.85 out of 5 average rating, 158 reviews

A cozy living area is depicted, featuring a comfortable sofa and two light blue armchairs. A wooden coffee table is centered in the space, while a small TV is positioned on a decorative cabinet. Soft lighting from floor lamps enhances the inviting atmosphere.

Condo in Sarasota

Siesta Key Ground Floor Condo 2BR On Trolley Line

A spacious screened lanai features a circular wooden table surrounded by two wooden chairs with patterned cushions. Potted plants and decorative items are placed on the table. Beyond the railing, palm trees and the vibrant blue of the Gulf coast are visible.