Charming Gillespie Park Bungalow with Pool in Downtown Sarasota
Step into this cozy yet elegant retreat nestled on a quiet street in the heart of Gillespie Park. This home blends vintage character with modern updates, offering everything you need for a relaxing vacation.
Situated less than 4 1/2 miles from Lido Beach and the famous St. Armands Circle, this home offers convenient access to sun, sand, and seaside dining and shopping. Close to Citrus Square and Downtown Sarasota, you'll enjoy world-class restaurants, theaters and shopping a short walk away.
The home features a recently updated kitchen that screams cottage charm, 2 walk-in showers, a sunroom, a butler's pantry/mudroom and the most relaxing sunroom around. There are also a washer and dryer on the premises.
The home features 2 bedrooms, one with a king size bed, the other with a queen bed and twin bed. Both bedrooms have a TV and there is a desk for remote work in the primary bedroom.
There is Wi-Fi and a 55" smart TV in the main living room for entertainment. If you would rather unwind without technology, there is a record player, games, puzzles and tons of books to enjoy during your stay.
This home is located less than a mile from the bay and bayfront park. It is half a block from Gillespie Park with the playground at the end of the street, 10 acres of walking trails, and access to tennis and pickleball courts (tennis rackets and pickleball paddles are available for you to use at the house).
But the best part is your very own backyard oasis with multiple seating areas, a grill area, an outdoor dining space, a beautiful mature oak tree dripping with Spanish moss, and your very own pool.
Guest Access & Parking
-Driveway and street parking available -Quiet, walkable neighborhood with sidewalks -Car recommended for beach and downtown access
Location Highlights
-Less than 4.5 miles to Lido Beach and St. Armands Circle -Minutes from Citrus Square and Downtown Sarasota’s dining and shopping -Easy access to parks, cultural attractions, theaters and local markets
Whether you're planning a beach getaway, a family vacation, or a peaceful retreat, this charming Sarasota bungalow offers the perfect blend of comfort, style, and location.
This is a vacation rental only. No bookings for group work trips, companies, or travel agencies. Reservations made on behalf of employees or coworkers will be canceled.
PLEASE NOTE: This home has a pool in the backyard for you to use when you stay with us. The pool is heated from November 15th to April 15th. Please observe pool rules posted. No diving allowed. By booking with us, you agree to use the pool at your own risk and we take no responsibility for injury or any accidents caused while utilizing the pool.
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The host requires you to complete the following before checking out:
Load and start the dishwasher
Remove personal items, remove leftover food and drinks and take out the rubbish
Turn off the lights and lock the doors
Please leave towels hanging and check them for stains and shout them before you go. We will gather them and wash them.
Please re-cover outdoor furniture.
Please make sure any books, beach towels & anything else borrowed from the home is returned.
Failure to complete these may result in a negative review from the host.
-Please observe pool rules posted. No diving allowed. By booking with us, you agree to use the pool at your own risk.
-Please no shoes in the house
-No use of home or internet for any illegal activities.
-No packages or mail delivered or accepted to the home.
-No Pets, we have major allergies.
-Please be mindful of keeping our couches and furniture clean or additional cleaning fees may apply.
-Please be respectful of our neighbors.
Important information
You need to know
Property # 4914028vb
Extra-person charges may apply and vary depending on property policy
Government-issued photo identification and a credit card, debit card or cash deposit may be required at check-in for incidental charges
Special requests are subject to availability upon check-in and may incur additional charges; special requests cannot be guaranteed
On-site parties or group events are strictly prohibited
Host has indicated that there is a carbon monoxide detector on the property
Host has indicated that there is a smoke detector on the property
About the area
Sarasota
Central Sarasota, a neighbourhood in Sarasota, is home to this holiday home. St. Armands Circle and Mall at University Town Center are worth checking out if shopping is on the agenda, while those wishing to experience the area's natural beauty can explore Lido Beach and Siesta Key Beach. Looking to enjoy an event or a game while in town? See what's happening at Ed Smith Stadium or Longboat Key Public Tennis Center.
Van Wezel Performing Arts Hall - 15 min walk - 1.3 km
Sarasota Opera House - 18 min walk - 1.6 km
Marina Jack - 5 min drive - 2.4 km
Marie Selby Botanical Gardens - 5 min drive - 2.4 km
Ringling College of Art and Design - 7 min drive - 2.8 km
Getting around
Sarasota, FL (SRQ-Sarasota-Bradenton Intl.) - 11 min drive
Restaurants
Kahwa Coffee - 14 min walk
Popeyes Louisiana Kitchen - 9 min walk
Rosemary & Thyme - 9 min walk
Rosemary Food + Beer - 11 min walk
Lefty's Oyster & Seafood Bar - 11 min walk
Frequently asked questions
Does Charming Gillespie Park Bungalow with Pool in Downtown Sarasota have a pool?
Yes, this property has an outdoor pool. Pool types include heated pools.
How much does it cost to stay at Charming Gillespie Park Bungalow with Pool in Downtown Sarasota?
As of 13 May, 2026, prices found for a 1-night stay for 2 adults at Charming Gillespie Park Bungalow with Pool in Downtown Sarasota on 23 Jul, 2026 start from S$286, including taxes and fees. This price is based on the lowest nightly price found in the last 24 hours for stays in the next 30 days. Prices are subject to change. Choose your dates for more accurate prices.
Is Charming Gillespie Park Bungalow with Pool in Downtown Sarasota pet-friendly?
No, pets are not allowed at this property.
How much is parking at Charming Gillespie Park Bungalow with Pool in Downtown Sarasota?
On-site parking is available at the property.
What time is check-in at Charming Gillespie Park Bungalow with Pool in Downtown Sarasota?
Check-in begins at 4:00 PM.
What time is check-out at Charming Gillespie Park Bungalow with Pool in Downtown Sarasota?
Checkout is at 10:00 AM.
Where is Charming Gillespie Park Bungalow with Pool in Downtown Sarasota located?
Located in Central Sarasota, this holiday home is within 1 mile (2 km) of Regal Hollywood - Sarasota, Sarasota County Visitor Information Center and History Museum and Sarasota Opera House. Van Wezel Performing Arts Hall and Florida Studio Theatre are also within 1 mile (2 km).
Reviews
10
Exceptional
Reviews are presented in chronological order, subject to a moderation process, and verified unless otherwise labelled.
This Florida-style bungalow is indeed charming and is in a great location. We could walk only 2 minutes to the public tennis courts in Gillespie Park and to shopping and restaurants downtown. The host is an excellent communicator and extremely attentive and friendly. We loved sitting and reading on the veranda the living and dining room are well-appointed. Great place to relax and enjoy Sarasota.
This home was lovely! It was comfortable for my husband and me. The location was close to great restaurants and the downtown area. Unfortunately, the weather didn’t cooperate with our plans, so we only used the pool once, but it was heated to a nice temperature. The outdoor space had plenty of seating options.
Jean S.
Stayed 7 nights in Feb 2026
About the host
Hosted by Shannon
We’re a couple raising young triplets who absolutely love Sarasota and everything it has to offer. Traveling with 3 little ones we felt that we needed a home base to make it easier and more realistic to travel often to visit friends and family in the area. We love hosting because we love when our guests fall in love with Sarasota the way we did and make it their home away from home too!
Why they chose this property
Gillespie park is the best neighborhood! It's close by Citrus Square, Gillespie park with its playground for our kids and walking trails and pickleball courts for us. We love how walkable everything is and how close we are to everything downtown has to offer. Lido is also our favorite beach in the area so it's so nice to be just 4 miles or a short 10 minute car ride away.
What makes this property unique
This property is so charming and when you walk through the front door into the sunroom, you can feel your shoulders drop and your brain switch into vacation mode. We love that the house is 100 years old and has withstood the test of time and it has been our honor to lovingly update it so it can continue to stand for another 100 years. We love the pool and the backyard reminds us of a little European courtyard.
Languages:
English
Premier Host
They consistently provide great experiences for their guests