
Holiday rentals with outdoor seating in Downtown Sarasota
Find and book unique Holiday Houses with Outdoor Seating on Airbnb
Top-rated Holiday Houses with Outdoor Seating in Downtown Sarasota
Guests agree: These Holiday Houses with Outdoor Seating are highly rated for location, cleanliness and more.

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!

Early Chkin, Elevator-4th fl 2mins-DT, 7mins-Airpt
Beach ready Apt!! Echo/white noise machine Beside Ringling College! 2 minutes from downtown Sarasota 7 mins - Airport Corner Apt Steps to the elevator 2 bicycles & 2 escooters Escape the ordinary and immerse yourself in an extraordinary stay at our unique Airbnb that's on a main road . 60+ amenities from a secure room safe to a luxurious, indulgent bed. Essential amenities such as grocery stores/pharmacies/ & CVS. less than a mile away. Send me a message if you have any questions .

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.

Sunshine House, close to Downtown
Great location! This is a family friendly home, close to downtown and beaches, with a pool, fenced yard, and a large, screened porch for lounging and having meals outside. Close to all the great things Sarasota has to offer- museums, gardens, theaters, shopping, Sarasota Bay, and beaches. The house is 1.5 miles from downtown, 10 min to St. Armands, 15 min to Lido Beach, and about 20 min Siesta Key Beach. One dog considered with a fee. Children must be supervised at all times in the pool area.

Duplex - just mins to Siesta Beach - Pet Friendly
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

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.

❤ Villa & Garden in Downtown ~ 5 Min to Beaches
Our bright and contemporary Heart Villa offers the quintessential Sarasota experience, combining downtown and beach attractions. It is nestled among tropical trees in a charming cul-de-sac in historic Laurel Park – right in the heart of downtown with loads of restaurants, boutiques, and sights on offer. Several fantastic beaches are just a 5-minute ride away! And the villa's private garden is the perfect place to enjoy alfresco dining! Certificate of Registration Number: VR24-00113

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

*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.

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.

Quiet Downtown Sarasota Villa. 2 bed 2 bath. 644
Enjoy a stylish experience at this centrally-located attached villa, in the heart of Laurel Park, in downtown Sarasota. 2 bedrooms and 2 bathrooms. All the modern conveniences including a new 75" smartTV, kitchen, private yard & free parking. Ground floor villa offering 2 bedrooms & 2 bathrooms. Bedroom 1 has a king sized bed, Bedroom 2 has 2 twin beds & the living room has a pull out sleeper sofa. BBQ available out back for grilling. Updated 2023.

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 Downtown Sarasota outdoor seating rentals
Holiday House Rentals with Outdoor Seating

Magical Secluded Retreat

Historic Downtown Sarasota - Gem I

Downtown Sarasota retreat. Home in Arlington Park.

Take a Siesta off Bahia Vista

Serenity Springs | Private Heated Pool + Waterfall

Private Siesta Beach House Oasis with Heated Pool.

Spacious Luxury Home/7 mi to Siesta Key/2 mi to DT

Sunshine House- Sarasota Pool Retreat
Apartment rentals with outdoor seating

Gillespie On The Park, Walk to Downtown

Funky & Fun Apartment in Central SRQ

Lido Key FL Studio/Efficiency 5

Come Enjoy Our Peaceful Retreat

Updated Old Florida Studio Getaway in Central SRQ

Modern Private Apartment 1 Block from Sarasota Bay

Serenity on the Manatee

Private apartment w/King bed+full kitchen
Condo rentals with outdoor seating

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

Crystal House on Siesta Key Beach

Lovely 2-Bedroom Condo, 7 min from Siesta Beach

Modern Studio · 5 min from Siesta Beach

Sun-Kissed Memories!

Near beach. Daily rentals. Pool. king bed

The Seashell Cottage with peaceful water views!

Siesta Key Condo. Checkout our great rates!
When is the best time to visit Downtown Sarasota?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $270 AUD | $300 AUD | $296 AUD | $229 AUD | $181 AUD | $180 AUD | $184 AUD | $190 AUD | $175 AUD | $187 AUD | $228 AUD | $249 AUD |
| Avg. temp | 16°C | 18°C | 20°C | 22°C | 25°C | 27°C | 28°C | 28°C | 27°C | 24°C | 20°C | 18°C |
Quick stats about holiday rentals with outdoor seating in Downtown Sarasota

Total holiday rentals
Explore 60 holiday rentals in Downtown Sarasota

Nightly prices starting at
Downtown Sarasota holiday rentals start at $99 AUD per night before taxes and fees

Verified guest reviews
Over 3,240 verified reviews to help you choose

Family-friendly holiday rentals
40 properties offer extra space and kid-friendly amenities

Pet-friendly accommodation
Find 40 rentals that welcome pets

Holiday rentals with a pool
10 properties feature pools

Rentals with dedicated workspaces
40 properties have a dedicated workspace

Wi-Fi availability
60 of Downtown Sarasota holiday rentals include Wi-Fi 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!
Destinations to explore
- Pet-friendly rentals Downtown
- Rentals with a fire pit Downtown
- Apartment rentals Downtown
- Family-friendly rentals Downtown
- Rentals with pools Downtown
- Rentals with a patio Downtown
- Rentals with a hot tub Downtown
- House rentals Downtown
- Fitness-friendly rentals Downtown
- Rentals with a washing machine and dryer Downtown
- Condo rentals Downtown
- Rentals with outdoor seating Sarasota
- Rentals with outdoor seating Sarasota County
- Rentals with outdoor seating Florida
- Rentals with outdoor seating United States
- Anna Maria Island
- Siesta Beach
- Crescent Beach
- Raymond James Stadium
- Busch Gardens Tampa Bay
- John's Pass
- Turtle Beach
- Coquina Beach
- Vinoy Park
- Caspersen Beach
- Lido Key Beach
- Amalie Arena
- Cortez Beach
- Bean Point Beach
- Anna Maria Public Beach
- Jannus Live
- ZooTampa at Lowry Park
- Manasota Key Beach
- River Strand Golf and Country Club
- Hard Rock Casino
- Englewood Beach
- North Beach At Fort DeSoto Park
- Splash Harbour Water Park
- Adventure Island




