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Holiday rentals with outdoor seating in Downtown Sarasota

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Top-rated rentals with outdoor seating in Downtown Sarasota

Guests agree: these rentals with outdoor seating are highly rated for location, cleanliness and more.

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Top guest favourite
A quaint cottage features a vibrant red door, framed by lush greenery and colorful plants. The path leading to the entrance is bordered by neatly arranged brick landscaping, enhancing the inviting entrance to the home.
Home in Laurel Park
4.98 out of 5 average rating, 146 reviews

The Sweet Spot! Walk to DT & Free Trolley to Beach

Looking for the Sweet Spot in Sarasota? Look no further! This artistically updated cottage, nestled in the quiet, historic downtown neighborhood of Laurel Park is a just a short walking distance to some of the best downtown dining, shopping, arts venues and the renowned Selby Gardens. Take the free Breeze Trolley to Siesta Key and Lido beach. Relax in the private outdoor courtyard. It's is the perfect place for a couple's getaway, a family vacation, or a long term stay. So book now and welcome!

Top guest favourite
A vibrant courtyard is filled with tropical plants, colorful lounge chairs, and a tiki bar. Unique garden decorations and a fish pond with a waterfall enhance the lively atmosphere. Striped umbrellas provide shade over the seating areas, creating a welcoming outdoor space.
Townhouse in Gillespie Park
4.95 out of 5 average rating, 388 reviews

Peacock🦚1/2 m Walk to Downtown #TheTropicalNut ☀️🥳👙

You are safe with me!Enhanced cleaning protocol in place- as per Airbnb guidelines. Welcome! Be yourself! A five star stay, guaranteed. You WILL be happy here! Special occasion? My favorite. I like doing special things for special people. Courtyard w/ lounge chairs, tiki bar, pond & cafe seating! Queen bed and a pullout couch with new mattress! A 1/2 m walk to downtown. 1 of 2 upstairs apartments at The Tropical Nut! We aim to please! No-regret-booking! Will consider-if asked-pets of all kinds!

Guest favourite
A light-filled living area features soft, neutral-toned sofas arranged around a glass coffee table atop a textured area rug. Decorative elements, such as a floral arrangement and softly glowing lamps, complement the inviting atmosphere. A doorway leads to the kitchen, enhancing the open layout.
Villa in Laurel Park
4.85 out of 5 average rating, 150 reviews

Updated Downtown Sarasota Villa, 2b/2b

Enjoy a stylish experience at this centrally-located 2 bedroom, 2 bathroom attached villa in historic Laurel Park, downtown Sarasota. New 75” smart TV! Sleeps 6. Bedroom 1: King bed w/ en suite bathroom. Bedroom 2: 2 queen beds. Granite kitchen. 2 bathrooms. Fenced outdoor paver patio w/washer & dryer. Updated 2022. Free parking outside villa. Walking distance to downtown Sarasota, Selby Gardens, Marina Jack, Main St & more. Pottery Barn furnishing, beachy vibe & free WiFi! Free parking too!

Guest favourite
An inviting living space showcases a comfortable seating arrangement, including two black lounge chairs and a stylish dining area. Natural light floods through large windows, illuminating a decorative shelf filled with coastal decor. A circular rug adds a touch of warmth to the wood flooring.
Home in Sarasota
4.96 out of 5 average rating, 132 reviews

5 Star! Walk/Bike DTN ~ 5 mi to Lido Beach Pets Ok

Bright & Comfy Downtown Home | Walk to Main St, Near Trolley to Lido Beach & St Armands. Centrally located in a quiet downtown neighborhood along the Legacy Bike Trail & Payne Park, this updated 3BR/2BA home is clean, cozy, and filled with coastal charm. Enjoy a screened-in lanai, a large, fenced backyard, WiFi, Smart TV with YouTube TV, BBQ, beach gear, washer/dryer and carport. Pets welcome! Prime Location: 1 mi to Main St dining. 2 mi to waterfront dining and boat tours. 5 mi to Lido Beach.

Guest favourite
A single-story home is surrounded by greenery and palm trees, showcasing a light green exterior. A narrow pathway leads to the entrance, flanked by decorative planters. The white fence adds charm and defines the front yard, with large windows allowing natural light into the interiors.
Villa in Laurel Park
4.88 out of 5 average rating, 297 reviews

Duplex-near beaches-historical area- Pets welcome

This is a 2/1 in Sarasota's Historic Laurel Park that offers a great downtown and beach experience! Walk/bike to historic downtown with shops, restaurants, bars, boutiques, parks, and music/theater. Minutes from the best beaches in the U.S. Enjoy the lanai & fenced backyard for privacy . Grill & enjoy your favorite beverage while watching your favorite show on the lanai ! Enjoy taking your pet for a walk & check out the historic homes in the area! Short term rental number VR24-00222

Top guest favourite
Guest house in Sarasota
4.95 out of 5 average rating, 145 reviews

Downtown Garden Studio close to everything

Welcome to my tropical 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.

Guest favourite
A well-lit bedroom features a spacious bed dressed in crisp linens, accented with an orange throw blanket. Two decorative wall sconces illuminate the room, while striped curtains frame the window, adding a modern touch. A woven basket and art pieces enhance the inviting decor.
Home in Gillespie Park
4.96 out of 5 average rating, 124 reviews

Mid-Century Circus Charm Near Downtown Sarasota

Retro circus romance & mid-century style near downtown Sarasota. ✅ Main Street, Downtown Sarasota 2 miles - 6 mins ✅ St. Armand’s Circle: 4.5 miles - 15 mins ✅ Lido Key Beach 5 miles - 15 mins ✅ Siesta Key Beach: 6 miles - 18 mins ✅ Downtown Bradenton 12 miles - 25 mins ✅ Bradenton Beach 14 miles - 30 mins ✅ Casey Key 16 miles - 30 mins ✅ Airport: Sarasota–Bradenton International Airport 6 miles - 12 minutes

Top guest favourite
Home in Bellevue Terrace
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

Top guest favourite
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
4.92 out of 5 average rating, 277 reviews

*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 favourite
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.
Guest house in Laurel Park
4.89 out of 5 average rating, 156 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.

Guest favourite
An outdoor area is shown with a walkway made of red pavers leading to a yellow building. A dining set with an umbrella is situated on a gravel surface, surrounded by potted plants. Decorative stones and landscaping enhance the inviting outdoor space.
Guest house in Gillespie Park
4.91 out of 5 average rating, 161 reviews

Perfect Florida location: Craftsman Carriage House

Beautiful accessory dwelling in downtown Sarasota designed to match and complement our historic 1920s bungalow main house, which can be booked separately on AirBnB. The 1BR/1BA carriage house apartment has all modern amenities, with a dedicated garage parking spot and a lovely outdoor porch. The carriage house features Craftsman-style details and is available for short- or long-term stays. Locally-based property management team on-call to ensure a pleasant stay.

Top guest favourite
The exterior of a charming adobe-style home is highlighted, featuring a light blue facade and a decorative entrance. A pathway leads to the door, bordered by colorful plantings and a white picket fence. Tropical plants add to the serene ambiance of the front garden.
Home in Sarasota
4.94 out of 5 average rating, 108 reviews

Downtown Sarasota | Casa de Zara

Welcome to Casa de Zara! Immerse yourself in Sarasota history by staying in our quaint Adobe style home built in 1925 with a serene garden filled with plants and trees native to Florida. You will be 1 mile from Main St. and 4 miles to Lido Key. One block over you will find a fun filled park with tennis and pickle ball courts, a walking path and basketball courts. Less than a mile away is Bayfront Park which is perfect for watching sunsets!

Popular amenities for outdoor seating rentals in Downtown Sarasota

KitchenWifiPoolFree parking on premisesAir conditioning

House rentals with outdoor seating

Top guest favourite
Home in Sarasota
4.98 out of 5 average rating, 110 reviews

Your DreamOasisAwaits: SiestaKeyEscape with Pool!

Guest favourite
A serene outdoor space features a circular fire pit surrounded by comfortable seating. Lush greenery enhances the setting, while the warm colors of a sunset fill the sky. The guest house is visible in the background, contributing to a cozy atmosphere for relaxation.
Home in Gillespie Park
4.94 out of 5 average rating, 86 reviews

Downtown Sarasota Guest House

Top guest favourite
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.
Home in Indian Beach-Sapphire Shores
4.99 out of 5 average rating, 104 reviews

Magical Secluded Retreat

Guest favourite
Home in Downtown Sarasota
4.96 out of 5 average rating, 48 reviews

Beach Escape+Downtown | large yard/Heated pool

Guest favourite
Home in Sarasota
4.93 out of 5 average rating, 104 reviews

[The Bay St. Hideaway]Private Swimming Pool& Patio

Guest favourite
The front entrance features a light pink facade with teal accents. A small, covered porch leads to a white door, bordered by decorative shutters and framed by a circular window. Lush greenery compliments the charming, inviting exterior.
Home in Laurel Park
4.95 out of 5 average rating, 22 reviews

Historic Cottage in Downtown Sarasota

Top guest favourite
Home in Arlington Park
4.97 out of 5 average rating, 129 reviews

The Wisteria Oasis W/swings, heated pool & hot tub

Guest favourite
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 Sarasota
4.98 out of 5 average rating, 131 reviews

The Mango House Beach Cottage

Apartment rentals with outdoor seating

Guest favourite
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.
Flat in Indian Beach-Sapphire Shores
4.97 out of 5 average rating, 165 reviews

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

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.
Flat in Sarasota
4.9 out of 5 average rating, 135 reviews

Funky & Fun Apartment in Central SRQ

Guest favourite
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.
Flat in Lido Key
4.85 out of 5 average rating, 119 reviews

Lido Key FL Studio/Efficiency 5

Top guest favourite
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.
Flat in Indian Beach-Sapphire Shores
4.99 out of 5 average rating, 134 reviews

Come Enjoy Our Peaceful Retreat

Top guest favourite
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.
Flat in Indian Beach-Sapphire Shores
4.96 out of 5 average rating, 180 reviews

ROYS PLACE Romantic, Private, Paradise!

Top guest favourite
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
4.97 out of 5 average rating, 235 reviews

Modern Private Apartment 1 Block from Sarasota Bay

Top guest favourite
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
4.97 out of 5 average rating, 450 reviews

Serenity on the Manatee

Guest favourite
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.
Flat in Sarasota
4.77 out of 5 average rating, 200 reviews

Private apartment w/King bed+full kitchen

Apartment rentals with outdoor seating

Top guest favourite
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.
Apartment in Siesta Key
5 out of 5 average rating, 156 reviews

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

Guest favourite
The balcony features a cozy seating arrangement comprising two chairs and a coffee table, all set against a stunning ocean view. The turquoise waters and sandy beach are visible beyond the railing, offering a serene backdrop for relaxation.
Apartment in Sarasota
4.99 out of 5 average rating, 105 reviews

6 Siesta Breakers - Condo, Ocean View, Heated Pool

Guest favourite
A cozy bedroom features a large green bed with multiple white pillows, complemented by two bedside lamps. The ceiling showcases a tropical leaf pattern, and mirrors adorn the walls. Natural light enters through a window, with white curtains framing the view.
Apartment in Bradenton
4.95 out of 5 average rating, 176 reviews

KING bed + Anna Maria Island Beaches + Beach Gear!

Top guest favourite
Apartment in Sarasota
4.98 out of 5 average rating, 125 reviews

Lovely 2-Bedroom Condo, 7 min from Siesta Beach

Guest favourite
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.
Apartment in Sarasota
4.97 out of 5 average rating, 130 reviews

Modern Studio · 5 min from Siesta Beach

Superhost
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.
Apartment in Sarasota
4.88 out of 5 average rating, 179 reviews

Lake View 1BR Condo | Heated Pool Near Siesta

Guest favourite
A bright living area features a white sectional sofa facing a modern fireplace set in a textured stone wall. A wooden coffee table sits atop a striped rug, with a beach-themed painting and a ceiling fan visible above, contributing to a relaxed ambiance.
Apartment in Siesta Key
4.88 out of 5 average rating, 117 reviews

Perfect Location in Siesta Key

Guest favourite
A private outdoor patio is highlighted, featuring a round table surrounded by four chairs. A large blue umbrella provides shade, while tropical greenery adds a natural backdrop. Paved brick flooring completes the inviting outdoor space, ideal for relaxation.
Apartment in Siesta Key
4.92 out of 5 average rating, 226 reviews

Steps to Beach & Siesta Key Village-Village condo

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Quick stats about holiday rentals with outdoor seating in Downtown Sarasota

  • Total holiday rentals

    Explore 70 holiday rentals in Downtown Sarasota

  • Nightly prices starting at

    Downtown Sarasota holiday rentals start at £51 per night before taxes and fees

  • Verified guest reviews

    Over 3,570 verified reviews to help you choose

  • Family-friendly holiday rentals

    40 properties offer extra space & child-friendly amenities

  • Pet-friendly holiday rentals

    Find 40 rentals that welcome pets

  • Holiday rentals with a pool

    20 properties feature pools

  • Rentals with dedicated workspaces

    40 properties have a dedicated workspace

  • Wifi availability

    70 of Downtown Sarasota holiday rentals include wifi access

  • Popular amenities for guests

    Guests love Kitchen, Wifi and Pool across Downtown Sarasota rentals

  • 4.9 Average rating

    Downtown Sarasota stays are highly rated by guests – averaging 4.9 out of 5!

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