Holiday rentals with outdoor seating in South Sarasota

A well-lit dining area features a modern table with four chairs, complemented by a floral artwork on the wall. Natural light enters through French doors, enhancing the bright and open atmosphere. A stainless steel refrigerator is visible, maintaining a clean and functional kitchen space.

4.9 out of 5 average rating, 115 reviews

Tropical Paradise minutes to #1 Siesta Key Beach

Location! Just minute to the #1 Beach in USA , Siesta restaurant and shopping. This cozy 2 bedroom/1 bath home feels very modern, comfortable and very functional. Tropical landscaping .Fully equipped kitchen. Beautiful private fenced backyard with Yoga platform. Beach chairs available. Perfect for a budget oriented traveler looking for immaculate home and convenient location close to Hwy 41 Siesta Beach and shopping and walking distance to restaurants. Primary guest must be 25 years of age.

ValueOutdoor spacesFamily

4.99 out of 5 average rating, 234 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!

ValueLocationKitchen

4.98 out of 5 average rating, 137 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!

Outdoor spacesLocationDecor

4.98 out of 5 average rating, 203 reviews

An indoor pool is enclosed within a screened area, offering a clear view of tranquil blue water and surrounding trees. Comfortable outdoor seating is visible, complemented by a sunlit patio space. Large glass doors provide access to the pool area, enhancing the open feel.

Home in South Sarasota

The Bradford Cottage/Heated Pool /Mins to Siesta

If you are looking for a cozy retreat in a safe and private neighborhood than look no further! From the minute you step inside this immaculate private residence you will feel right at home. With a beautiful open floor plan with plenty of room to spread out, natural light that pours in every room and a spacious back porch overlooking the heated pool this is the perfect place to unwind and relax. Minutes from the #1 rated Siesta Key beach and downtown Sarasota you are in the middle of it all!

Outdoor spacesValueHospitality

4.95 out of 5 average rating, 414 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)

Outdoor spacesValueBiking

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.

4.87 out of 5 average rating, 136 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.

ValueLocationBackyard

Guest suite in South Sarasota

The studio features a spacious layout with a king size bed adorned with light bedding. A comfortable chair is positioned beside the bed, and a patterned area rug covers the floor. Natural light filters in through the window with striped blinds.

4.87 out of 5 average rating, 198 reviews

Cozy Eco Private Studio 10 min to Downtown & Beach

This is a delightful, renovated eco-friendly little studio attached to the right side of the main house. We clean everything with natural products. It is bright and spacious and it has a private entrance, and a parking space. There is a small kitchenette with cooking basics, a separate full bathroom, and a king size bed. It is nested in very convenient location, close to everything. It is located a few miles from downtown Sarasota as well as 5-6 miles from Siesta Key and Turtle Beach.

LocationValueTV

4.96 out of 5 average rating, 162 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

A perfect blend of Sarasota’s architectural heritage and contemporary elegance right in the heart of Arlington Park. This bright, newly renovated 2 bed/2 bath & pull out sofa in a mid-century gem offers a serene escape, providing a refreshing interplay of historical charm and modern luxury. Enjoy the separate sunroom/office for those working from home, or use as an extra sleeping space with comfy pull out sofa. Take a break with a quick dip in the sparkling pool. VR24-00160

Outdoor spacesValueNearby

4.95 out of 5 average rating, 192 reviews

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

Outdoor spacesValueCheckout

4.98 out of 5 average rating, 116 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. 🌴

Outdoor spacesLocationBarbecue

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.

4.9 out of 5 average rating, 151 reviews

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

Bright second-floor 1-bedroom condo 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 convenient location close to shopping and dining.

LocationValueAccess

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.

4.99 out of 5 average rating, 192 reviews

Turtle Nest Oasis • Hot Tub • 5 mi to Siesta Key

🐢Escape to 'The Turtle Nest,' a peaceful 3BR/2BA Sarasota oasis for 6. Just 5 miles from Siesta Key Beach, this private home is perfect for families or romantic getaways. Enjoy a lush backyard with a bubbling hot tub, a dedicated workspace, and all the beach gear you need for a seamless tropical retreat. Your perfect Florida vacation starts here!

ValueLocationHot tub

Popular amenities for South Sarasota outdoor seating rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Holiday House Rentals with Outdoor Seating

4.98 out of 5 average rating, 113 reviews

Pool, Shuffleboard, EV charg, Near beach, UTC mall

ValueOutdoor spacesParking

4.91 out of 5 average rating, 22 reviews

A private backyard features a heated in-ground pool surrounded by spacious pavers. Lounge chairs are positioned along one side, with a shaded table and umbrella nearby. Lush greenery lines the perimeter, providing a natural backdrop for relaxation and leisure.

Home in South Sarasota

The Pink Pineapple - Your Cozy Sarasota Home

LocationGetting aroundBathroom

Home in Gulf Gate Estates

A private backyard features a large fire pit surrounded by six wooden chairs, offering an inviting space for gatherings. Lush greenery decorates the perimeter, with a colorful game set visible in the background. A shaded seating area with a blue canopy is positioned nearby.

5 out of 5 average rating, 27 reviews

Big backyard hangout, firepit, large primary suite

Outdoor spacesLocationBackyard

4.93 out of 5 average rating, 397 reviews

Heated&Renovated Pool•Beach Retreat•15m to Siesta

ValueLocationBackyard

A vibrant sunset lights up the sky in shades of orange and pink, framed by tall trees that line a quiet street. The silhouettes of palm trees add to the tropical ambiance, while homes are visible in the background, nestled among the lush landscaping.

4.92 out of 5 average rating, 106 reviews

Spectacular Sunsets! 15 min Siesta Key!

Outdoor spacesValueHot tub

4.79 out of 5 average rating, 19 reviews

The Siesta Key Pool House – Private Inland Oasis

Outdoor spacesLocationComfort

4.95 out of 5 average rating, 108 reviews

A single-story home is showcased with a light exterior and grey roof. Blue shutters adorn the windows, while lush greenery and colorful landscaping enhance the front yard. A screened wraparound porch offers additional outdoor space. The property is bordered by a paved walkway.

Home in Arlington Park

Sarasota 2B/2B Near Siesta Key/Arlington Park/SMH

LocationValueCondition

Home in Gulf Gate Estates

The exterior of a charming cottage is framed by a white fence and lush greenery. A welcoming archway leads to a porch adorned with large windows, offering glimpses of the intricate woodwork and vibrant flowering plants that enhance the entrance.

4.96 out of 5 average rating, 47 reviews

The Ashton Retreat

Outdoor spacesLocationTV

Apartment rentals with outdoor seating

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, 169 reviews

Free Prkn, Early Chkin, Elevator-4th fl airport/DT

LocationValueView

A modern studio layout features a queen bed with a blue floral bedspread, complemented by a comfortable futon and decorative pillows. A small dining table with two chairs is positioned near the seating area, while large blue curtains frame the window, allowing natural light to enter.

4.87 out of 5 average rating, 184 reviews

Chic & Cozy Getaway • Near Siesta Key Beach

Outdoor spacesValuePets

Superhost

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.

4.9 out of 5 average rating, 138 reviews

Funky & Fun Apartment in Central SRQ

Outdoor spacesValueCheck-in

4.84 out of 5 average rating, 126 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

ValueLocationCondition

A covered seating area is furnished with comfortable wicker chairs and lounge chairs featuring green cushions. Lush plants and palm trees enhance the outdoor space, while a view of the shared garden can be seen in the background. A book and a sun hat rest on a side table.

4.9 out of 5 average rating, 116 reviews

Minutes to Siesta or DT w/heated pool and Hot Tub

Outdoor spacesValueBiking

4.99 out of 5 average rating, 112 reviews

A modern living area features a comfortable white sofa adorned with decorative pillows and a light-colored coffee table. A wall-mounted TV is positioned above a stylish console, while a cozy armchair and indoor plants add warmth. Soft lighting is diffused through natural daylight.

Apartment in Siesta Key

Modern Chic Getaway 2 Min. Walk to Beach & Village

LocationValueFamily

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.

4.97 out of 5 average rating, 240 reviews

Modern Private Apartment 1 Block from Sarasota Bay

ValueOutdoor spacesAmenities

4.97 out of 5 average rating, 459 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.

Apartment in Ellenton

Serenity on the Manatee

ValueLocationHeating

Condo rentals with outdoor seating

A modern living room features a light-colored leather sofa and armchairs, complemented by a colorful area rug. A wall-mounted TV is positioned against a textured stone wall, with natural light filtering through sliding glass doors that lead to a screened-in patio.

5 out of 5 average rating, 161 reviews

❤️ Hidden Gem steps away from #1 beach 🏖 Siesta Key

ValueLocationAccess

A spacious bedroom features a modern white bed with plush pillows and a decorative brown pillow. A mirrored closet reflects the elegantly decorated space, which includes a stylish bedside table and soft lighting from a lamp. Natural light filters through the vertical blinds.

4.91 out of 5 average rating, 122 reviews

The Honeymoon Suite on Siesta Key Beach

Outdoor spacesLocationComfort

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, 382 reviews

On the Beach; Siesta Key SunBum Studio

Outdoor spacesValueBathroom

4.98 out of 5 average rating, 127 reviews

Condo in Sarasota

Lovely 2-Bedroom Condo, 7 min from Siesta Beach

Outdoor spacesLocationParking

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

Outdoor spacesLocationSleep quality

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.

4.84 out of 5 average rating, 163 reviews

Siesta Key Ground Floor Condo 2BR On Trolley Line

ValueLocationHospitality

4.79 out of 5 average rating, 105 reviews

Beachwalk Townhouse with view of Gulf of Mexico

ValueOutdoor spacesCheckout