Gillespie Park vacation rentals

We found 159 vacation rentals — enter your dates for availability

Discover a selection of 13 homes and other vacation rentals in Gillespie Park that are perfect for your trip. Whether you’re staying in a vacation home with family, friends, or just your furry companion, you'll find the amenities you need and want, which might include WiFi and a hot tub. Whatever you're looking for, you'll find a rental that has what everyone needs, including accessible or non-smoking choices.

Vacation rentals with weekly discounts - Gillespie Park

Showing deals for:Apr 24 - May 1

Image gallery for Villa & Garden in Downtown Sarasota ~ Walkable to downtown, 5 Minutes to Beaches

Living area
9.8 out of 10, Exceptional, (16 reviews)
Exceptional
(16 reviews)

Villa & Garden in Downtown Sarasota ~ Walkable to downtown, 5 Minutes to Beaches

Sarasota

9% off
Price is $327
$2,286 for 7 nights
All fees included
Villa & Garden in Downtown Sarasota ~ Walkable to downtown, 5 Minutes to Beaches

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Find out more about Gillespie Park

Why visit Gillespie Park

  • Outdoor Family Fun: Gillespie Park is ideal for family vacations with its scenic walking trails and a leash dog park.
  • Recreational Activities: Nearby Acre Park offers additional recreational options for visitors seeking adventure.
  • Relaxing Atmosphere: The charming neighborhood provides a peaceful environment for relaxation and exploration.
  • Vibrant Downtown: A short distance away, downtown Sarasota features a lively dining and shopping scene.
  • Comfortable Accommodations: Enjoy various vacation rentals with pet-friendly options and convenient amenities.

Popular types of accommodation around Gillespie Park

Planning a getaway to Gillespie Park? You're in for a treat. Discover the most sought-after vacation rentals, including private homes, condos, and apartments. Enjoy pet-friendly options, free parking, and access to fitness areas. Plus, take advantage of facility rentals to enhance your stay. Experience the charm of Sarasota, FL, while enjoying the comfort and convenience of your perfect vacation home.

  • Houses: The top choice for visitors to Gillespie Park, offering spacious and comfortable accommodations ideal for families, friends, or couples.
  • Condos: A popular option for travelers, providing modern amenities and great locations close to attractions.
  • Apartments: A convenient choice for those seeking a home-like atmosphere with easy access to local dining and shopping.
  • Villas: These luxurious retreats offer privacy and upscale features, perfect for a relaxing getaway.
  • Cottages: A quaint and charming option for a cozy stay, often nestled in serene surroundings.**

Top attractions near Gillespie Park

Gillespie Park in Sarasota, Florida, is perfect for outdoor family vacations, offering a blend of urban parks, beaches, and marinas. Explore scenic walking trails, enjoy the leash dog park, and visit nearby Acre Park for more recreational activities. Whether you're seeking relaxation or adventure, Gillespie Park and its surrounding attractions cater to travelers looking for a memorable experience in the heart of the city.

  • Siesta Key Beach: Renowned for its powdery white sands and crystal-clear waters, Siesta Key Beach offers a perfect beach vibe for relaxation and sunbathing, just 5 miles away from Gillespie Park.
  • St. Armands Circle: This lively street, located 3 miles from Gillespie Park, is famous for its upscale shops, dining options, and vibrant atmosphere, providing a unique city vibe perfect for exploring.
  • Marina Jack: Situated only 0.8 miles from Gillespie Park, Marina Jack offers outdoor adventures with boating, dining, and stunning waterfront views, capturing the essence of beach vibes and adventure.

Things to do recommended for couples

For a romantic getaway near Gillespie Park, enjoy a concert at Beatrice Friedman Symphony Center, just 0.8 miles away. For some fun, visit Evie's Golf Center for mini-golf, 5 miles away, or dive into adventure with Blue Water Explorers, located 13 miles away for underwater sports.

Things to do recommended for families

Your family will love visiting Ed Smith Stadium for an exciting sports experience just 1 mile from Gillespie Park. Enjoy the serene atmosphere at Nathan Benderson Park, located 6 miles away, and have fun at the Robert L. Taylor Community Complex, 2 miles away, offering various recreational activities.

Things to do recommended for groups

Experience the cultural charm of the Van Wezel Performing Arts Hall, just 0.7 miles from Gillespie Park. Enjoy a scenic hike at Sarasota BayWalk, 3 miles away, or share laughs at McCurdy's Comedy Theatre, 2 miles from the park. Perfect for group fun.

*Distances are measured in a straight line; actual driving distances may vary depending on the route.

What do I need to keep in mind when booking a vacation around Gillespie Park

When planning your trip, whether you’re traveling with a group, enjoying a family getaway, bringing along your pets, or seeking extended stays, be sure to use the appropriate filters to match your priorities. Here are some helpful Vrbo booking tips to assist you.

  • Traveling to Gillespie Park with a group: Think about how many bedrooms you'll require, as well as features like a full kitchen or outdoor area for group gatherings. The good news is, you can easily filter for all of these options and more on Vrbo.
  • Traveling to Gillespie Park with young kids: Traveling with little ones can be tough. It's important to prioritize their comfort and safety, along with suitable amenities like a private swimming pool. Additionally, it’s wise to think about how close you are to family-friendly attractions.
  • Taking your pets with you to Gillespie Park: For many families, a vacation isn't truly fulfilled without their beloved pet by their side. If that resonates with you, explore Vrbo listings that welcome pets. Most of these pet-friendly accommodations come equipped with feeding bowls and cozy beds, ensuring that everyone feels comfortable and at home.
  • Planning for a long term stay visiting Gillespie Park: If you're in search of vacation rentals that offer discounts for stays of a month or more, you've come to the right spot. By using the appropriate filters, you can effortlessly discover and save on monthly rentals. Don't forget to include options like a parking space, a well-equipped kitchen, or a private pool in your search as well.

Where to stay near Gillespie Park

Discover the charm of Gillespie Park, a delightful neighborhood in Sarasota, Florida, perfect for family vacations and outdoor adventures. Enjoy the relaxing atmosphere as you explore the wonderful little park, visit the dog park, and wander through the scenic streets. Just a short distance away, downtown Sarasota offers vibrant dining and shopping experiences, making it an ideal base for your tropical getaway. Embrace the friendly community and create lasting memories in this picturesque locale.

  • Sarasota: Nestled along Florida's Gulf Coast, Sarasota is a vibrant city known for its stunning beaches and rich cultural scene. Gillespie Park serves as your gateway to this coastal paradise, where travelers can indulge in family-friendly activities, shopping at local malls, and enjoying the resort-like atmosphere. Visit iconic landmarks such as Siesta Key Beach, renowned for its soft, white sands, or explore the charming town neighborhoods filled with unique shops and eateries that reflect the local flavor.
  • Central Sarasota: A mere 0.3 miles from Gillespie Park, Central Sarasota is a welcoming neighborhood perfect for families and beach lovers. This area provides access to recreational spaces and shopping centers, making it an ideal spot for both relaxation and exploration. Enjoy the nearby urban parks and family-friendly beaches that offer a variety of activities, from picnicking to water sports. The neighborhood's convenient location allows visitors to experience the best of Sarasota's beach culture while enjoying community-driven events.
  • Downtown Sarasota: Located 0.6 miles from Gillespie Park, Downtown Sarasota is a bustling hub that combines family-friendly experiences with a vibrant business atmosphere. This city center is known for its diverse shopping areas, where you can find everything from boutique shops to popular retail chains. Nearby urban parks and stunning beaches provide a perfect backdrop for outdoor activities, while cultural attractions like theaters and art galleries offer a taste of the local arts scene. Downtown Sarasota invites visitors to experience a blend of leisure and urban excitement.

Booking with Vrbo is simple

Are you eager to save on your upcoming trip? One effective strategy is to remain flexible with your travel dates, as prices can vary significantly. Additionally, opting for an extended stay often leads to substantial savings. To discover the perfect Vrbo property that fits your budget, take advantage of our filters to narrow your search by price, location, and type of vacation rental.

Unlock savings with One Key

Secure your group trip by booking an eligible Vrbo and earn OneKeyCash on your reservation. Being the planner definitely has its perks. When you join our travel rewards program, One Key, you’ll gain immediate access to member savings and the ability to earn and redeem OneKeyCash on qualifying bookings. Sign up today and begin enjoying your savings.

Vrbo Trips: Planning made easy

Vrbo's cutting-edge Trip Board offers you a convenient way to plan new trips, pick up right where you left off, and keep your travel plans organized. You can easily find properties you've saved or booked in the sections for Potential, Upcoming, or Current Trips. To get started with Trip Boards, simply visit: https://www.vrbo.com/trips.

**Based on Vrbo properties bookings.

Frequently asked questions

What is the most popular type of vacation rental in Gillespie Park?
In Gillespie Park, vacation houses are the most popular type of rental, with about 12 available in the area. These homes typically offer spacious layouts, multiple bedrooms, and fully equipped kitchens, making them ideal for families or groups looking for a comfortable stay. Additionally, there are several apartments and cottages scattered throughout the neighborhood, providing further options for travelers. Many of these properties feature amenities such as outdoor patios or decks, allowing guests to enjoy the pleasant Florida weather.
Are there any beach house rentals in Gillespie Park?
In Gillespie Park, Florida, several beach house rentals are available, providing travelers with charming accommodations in a vibrant neighborhood. These beach houses typically feature spacious layouts, multiple bedrooms, and fully equipped kitchens, making them superb for families or groups. Many properties include outdoor areas such as private patios or decks, ideal for enjoying the warm Florida weather. Additionally, guests can expect amenities like pool access, BBQ facilities, and proximity to local parks and attractions, adding to the overall vacation experience.
How much does it cost to rent a vacation home in Gillespie Park?
Prices for vacation rentals in Gillespie Park vary based on factors like travel dates, length of stay, accommodation type, and location. Simply enter your trip details to explore a wide range of options—whether you're traveling solo, as a couple, with family, or in a group. Vrbo offers something for every taste and budget, from affordable rentals in Gillespie Park to more spacious homes. To get the best value, book early and take advantage of Vrbo's free rewards program.
Are there any discounts for Gillespie Park vacation house rentals?
You can find great discounts on house rentals in Gillespie Park on Vrbo, including special rates on new listings and savings for weekly or monthly stays with top amenities such as a pool or parking. There are several discounts for Last minute bookings, and Early bird bookings too. The best part is, there's no need for a discount code—just enter your travel dates and apply the discount filters to view the top rates.
What are popular rental amenities in Gillespie Park?
In Gillespie Park, vacation rentals typically feature a range of amenities that cater to travelers' needs. Most properties include a fully equipped kitchen, great for preparing meals during your stay. Many rentals also come with outdoor spaces like patios or decks, allowing guests to enjoy the pleasant Florida weather. Additional amenities often found in these rentals include a coffee and tea maker for those cozy mornings and kitchen islands that provide extra cooking space or a casual dining area.
Are there any family house rentals in Gillespie Park?
In Gillespie Park, Florida, there are numerous family-friendly house rentals available, with around 11 options to choose from. This vibrant neighborhood is known for its proximity to beautiful parks and local attractions, making it an ideal spot for families. Many of these homes offer spacious layouts, fully equipped kitchens for preparing family meals, and comfortable living areas where everyone can unwind after a day of exploring.

Visitors can take advantage of nearby amenities such as playgrounds and picnic areas at Gillespie Park itself, which provides a wonderful setting for outdoor activities. Additionally, the area is just a short drive from the charming downtown Sarasota, where families can enjoy a variety of dining options and cultural experiences.
Can I rent a vacation home with a pool or hot tub in Gillespie Park?
In Gillespie Park, Florida, travelers can find several vacation homes available for rent that feature both pools and hot tubs. This charming neighborhood offers a mix of properties, including cozy bungalows and spacious family homes, ideal for relaxation and leisure. Many of these rentals come equipped with private pools, inviting hot tubs, and outdoor living spaces, superb for enjoying the sunny Florida weather. Additionally, amenities such as fully equipped kitchens, comfortable living areas, and Wi-Fi are commonly included, ensuring a comfortable stay for families or groups.
Are there any Gillespie Park vacation rentals with parking?
Vrbo offers a wide selection of vacation rentals in Gillespie Park with parking available—perfect for families or travelers who value the convenience of having a car during their stay. To easily find these properties, simply enter your travel details on Vrbo and use the "Parking available" filter under the amenities section. This makes it quick and easy to browse listings that suit your needs, whether you're planning a short city break or a longer stay.
Are there pet-friendly vacation rentals in Gillespie Park?
In Gillespie Park, you can find several pet-friendly vacation rentals that cater to both you and your furry companions. This charming neighborhood boasts a variety of accommodations, ranging from cozy cottages to spacious homes, many of which come equipped with modern amenities such as fully stocked kitchens, private gardens, and outdoor spaces ideal for pets.

The area is also close to several parks, providing ample opportunities for walks and outdoor activities with your pet. Nearby, the Gillespie Park itself is a lovely green space featuring walking trails, picnic areas, and plenty of room for your dog to roam. Additionally, the community is known for its welcoming atmosphere and pet-friendly cafes, making it easy to enjoy a meal out without leaving your pet behind.
Can I find long-stay vacation rentals in Gillespie Park?
A long-stay vacation rental in Gillespie Park is the best way to experience local living. Plus, you can make the most of long-stay discounts. For month-long stays, save an average of 19%, and for week-long bookings you can save an average of 10%.* Long-stay discounts are applied automatically when you enter your vacation dates into the search tool, or you can use the "Weekly stay" and "Monthly stay" filters in your search.

*Based on analysis of Vrbo booking and occupancy data for 2024 stays.
When is the best time to visit Gillespie Park for a vacation rental?
March is the most popular time to visit Gillespie Park, attracting travelers who are eager to enjoy the warm, sunny weather and vibrant local atmosphere. During the peak season from January to March, visitors can take advantage of comfortable temperatures, typically ranging from the mid-50s to low 80s Fahrenheit. This climate is ideal for outdoor activities such as hiking, biking, and exploring the scenic beauty of the park.

The thrilling energy of this season makes it superb for those looking to engage in community events and outdoor festivals. Visitors can partake in various recreational activities while soaking in the stunning views of the lush landscapes that surround Gillespie Park.

For those seeking a more budget-friendly option, consider planning your visit in October. This month offers a quieter experience, ideal for leisurely strolls and enjoying the park's natural beauty without the crowds. The weather remains pleasant, providing a fantastic backdrop for relaxation and exploration.

Ultimately, whether you're drawn to the lively peak season or the tranquil charm of the shoulder months, Gillespie Park offers a variety of experiences tailored to the adventurous traveler.
Are there any remote work vacation rentals in Gillespie Park?
In Gillespie Park, Florida, there are several remote work vacation rentals available, with about 13 options to choose from. This neighborhood is known for its vibrant atmosphere and proximity to downtown Sarasota, making it an excellent choice for those who need to balance work and leisure. Travelers can expect properties equipped with amenities tailored for remote work, including high-speed Wi-Fi, dedicated desk spaces, and comfortable office chairs. Many rentals also boast additional features like fully equipped kitchens, outdoor spaces for relaxation, and cozy living areas, ensuring a comfortable stay for both work and relaxation.

Gillespie Park itself offers a lovely green space for outdoor walks or breaks, and the nearby downtown area provides a variety of dining and entertainment options. To help narrow your search, insert your dates and apply the "WiFi" filter on Vrbo.
How early should I book a Gillespie Park vacation rental?
Book your Gillespie Park vacation rental at least two months before you travel for the best selection of properties.* Plus, you'll typically find that the earlier you book your vacation rental, the better the price.

*Based on analysis of Vrbo booking and occupancy data for 2024 stays.
What are the top attractions in Gillespie Park?
In Gillespie Park, visitors can enjoy a variety of attractions that highlight the area's charm. The neighborhood features Gillespie Park itself, a lovely green space superb for picnics, leisurely walks, and outdoor activities. Nearby, the vibrant arts scene can be explored with local galleries and studios showcasing the work of talented artists. The proximity to downtown Sarasota provides easy access to attractions such as the Ringling Museum of Art and the historic Asolo Theater, ensuring a rich cultural experience.
Can I change or cancel my Gillespie Park home rental booking on Vrbo?
To find Gillespie Park vacation rentals with free cancellation, just use Vrbo's handy "Free cancellation" search filter. We get that plans can change, so it's easy to filter properties that give you flexibility. If you need to make changes to an existing booking, drop your host a message. Go to "My Trips" in your account, click "Change or Cancel" and then "Message Host". Vrbo rentals give you the privacy of having the entire place to yourself, and for extra flexibility, some travelers can choose to pay over time with Affirm. Whether you're adjusting your plans or looking for flexible payment options, Vrbo makes it easy to book with confidence.
Why should I join Vrbo as a host?
Joining Vrbo as a host opens the door to a global community of travelers seeking unique stays, giving you the opportunity to earn income from your property on your terms. With user-friendly tools, dedicated support, and exposure on major travel sites, Vrbo makes it easy to list, manage, and succeed. Whether it's a cozy cabin or a beach condo, you can turn your space into a standout destination, become a host and let Vrbo handle the heavy lifting to help you thrive.Earn a Premier Host badge by providing quick, reliable communication and consistently delivering outstanding guest experiences.
Are all fees included in the Gillespie Park vacation rental prices shown on Vrbo?
Vrbo provides upfront pricing from the moment you start your search. There are no hidden fees added during the check-out process. This allows you to compare properties with ease and plan your trip with confidence.
What is VrboCare™ and how does it work?
Vrbo's mission is to help guests relax, reconnect, and enjoy precious time together. With VrboCare™, you can have peace of mind knowing you're protected and that if something goes wrong, we will do our best to make it right as applicable.If a significant issue arises that your host can't resolve, we'll help you address it, find a similar property, or get your reservation refunded if applicable. That's our promise. If a home is significantly different than listed, we'll get you into a new space that meets your needs and makes it right, or if a host cancels before your stay, you have a dedicated support team to get you into a similar home as applicable.
What can I expect from Vrbo customer service and VrboCare™ support?
Your peace of mind is our priority. Whether you're planning your trip or have already finished your stay, VrboCare™ is here to support you every step of the way. For urgent situations like last-minute cancellations, booking issues, or potential fraud, Vrbo customer service is available 24/7 to help resolve problems quickly and effectively.Vrbo also offers support via live chat through our Help Center, where you can find helpful resources on bookings, payments, property management, and safety, making it easy to get instant answers to many common questions.
Can I plan a group trip on Vrbo?
Vrbo's Trip Planner makes organizing group trips easy and stress-free. Whether you're planning with friends or coordinating a large group, you can collaborate in one place, save and share properties, vote on favorites, and build the perfect itinerary together.

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