Located in Central Sarasota within a short walk of Westcoast Black Theatre Troupe, Charming Gillespie Park Bungalow with Pool in Downtown Sarasota is within a mile (2 km) of Regal Hollywood - Sarasota.
Van Wezel Performing Arts Hall - 15 min walk - 0.8 miles
Sarasota Opera House - 15 min walk - 0.8 miles
Marina Jack - 18 min walk - 1.0 mile
Ed Smith Stadium - 6 min drive - 1.3 miles
Ringling College of Art and Design - 6 min drive - 1.5 miles
Getting around
Sarasota-Bradenton Intl. Airport (SRQ) - 11 min drive
Restaurants
Kahwa Coffee - 14 min walk
Popeyes Louisiana Kitchen - 9 min walk
Rosemary Food + Beer - 11 min walk
Rosemary & Thyme - 9 min walk
Lefty's Oyster & Seafood Bar - 11 min walk
About this property
Entire place
You'll have the entire home to yourself and will only share it with other guests in your party.
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.
For entertainment, guests can enjoy TVs. Private pools, washing machines, and 2 bathrooms are other standard amenities.
You will receive an email from the host with check-in and check-out instructions
Information provided by the property may be translated using automated translation tools
Check-out instructions
The host requires you complete the following before checking out:
Load and start the dishwasher
Remove personal items, remove leftover food and drinks, and take out the trash
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.
Rules
-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.
Pets
This property doesn't allow pets
Children and extra beds
Children allowed: ages 0-17
Events
No events allowed
Smoking
Smoking is not permitted
Important information
You need to know
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
Onsite parties or group events are strictly prohibited
Safety features at this property include a carbon monoxide detector and a smoke detector
This property is managed through our partner, Vrbo. You will receive an email from Vrbo with a link to a Vrbo account, where you can change or cancel your reservation
Check-in: 4:00 PM
Check-out: 10:00 AM
Minimum check-in age: 25
We should mention
Details about charges, deposits, or other important information:
This property is managed by a professional host. The provision of housing is linked to their trade, business, or profession.
Charges for extra guests may apply and vary depending on the property's policy.
A cash deposit, credit card, or debit card for incidental charges, as well as a government-issued photo ID, may be required at check-in.
Special requests are subject to availability at the time of check-in and can't be guaranteed. Certain requests may come with additional charges.
Onsite parties or group events are strictly prohibited.
Onsite safety features include a carbon monoxide detector and a smoke detector.
Frequently asked questions
Will I be able to park at Charming Gillespie Park Bungalow with Pool in Downtown Sarasota?
Does Charming Gillespie Park Bungalow with Pool in Downtown Sarasota feature a casino at the property?
No, Charming Gillespie Park Bungalow with Pool in Downtown Sarasota doesn't have a casino.
Does Charming Gillespie Park Bungalow with Pool in Downtown Sarasota have a restaurant with a breakfast menu?
No, Charming Gillespie Park Bungalow with Pool in Downtown Sarasota doesn't have a restaurant that serves breakfast.
Will Charming Gillespie Park Bungalow with Pool in Downtown Sarasota allow pets to stay for free?
No, pets aren't allowed at Charming Gillespie Park Bungalow with Pool in Downtown Sarasota.
How close is the airport from Charming Gillespie Park Bungalow with Pool in Downtown Sarasota?
The closest major airport to Charming Gillespie Park Bungalow with Pool in Downtown Sarasota is Sarasota-Bradenton Intl. Airport (SRQ), which is 4.1 mi away (11 minutes by car). Another top airport is St. Petersburg, FL (SPG-Albert Whitted), which is around 29.7 mi away.
Charming Gillespie Park Bungalow with Pool in Downtown Sarasota Reviews
Reviews
10
Exceptional
All reviews shown are from real guest experiences. Only travelers who have booked a stay with us can submit a review. We verify reviews according to our guidelines and publish all reviews, positive or negative.
Rating 10 - Excellent. 1 out of 1 reviews
10 - Excellent
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Rating 8 - Good. 0 out of 1 reviews
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Rating 6 - Okay. 0 out of 1 reviews
6 - Okay
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Rating 2 - Terrible. 0 out of 1 reviews
2 - Terrible
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10/10
Cleanliness
Reviews
10/10 Excellent
Jean S.
Feb 19, 2026
Liked: Cleanliness
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.