Gillespie Park holiday lettings

We found 155 holiday rentals — enter your dates for availability

Discover a selection of 10 homes and other holiday rentals in Gillespie Park that are perfect for your trip. Whether you’re staying in a holiday home with your children and pets or just with friends, you'll find the amenities that you need and want, which might include a garden and pool. No matter what you're looking for, you'll be sure to find a property to rent that has what everyone needs, including a place that's non-smoking or offers accessibility.

Holiday rentals with weekly discounts - Gillespie Park

Showing deals for:22 May - 29 May

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Frequently asked questions

What is the most popular type of holiday rental in Gillespie Park?
In Gillespie Park, holiday houses are the most popular type of holiday rental, with around 27 available in the area. These houses typically provide spacious rooms, featuring multiple bedrooms, fully equipped kitchens, and private outdoor spaces, making them ideal for families or groups seeking a comfortable retreat.
Are there any beach house rentals in Gillespie Park?
In Gillespie Park, several beach house holiday rentals are available, providing a lovely option for visitors looking to enjoy the coastal charm. These rentals are typically situated in pleasant neighbourhoods, offering easy access to local attractions and the beautiful beaches nearby. Guests can expect amenities such as fully equipped kitchens for preparing meals, comfortable living areas for relaxation, and outdoor spaces like patios or decks that allow for enjoying the warm Florida weather.
How much does it cost to rent a holiday home in Gillespie Park?
Prices for holiday 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 holiday 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, popular holiday rental amenities include fully equipped kitchens, allowing guests to prepare their own meals. Many properties feature outdoor spaces such as decks or patios, great for enjoying the pleasant Florida weather. Onsite parking is also a common convenience, making it easy for travellers to come and go. Additionally, several rentals permit pets, suiting those who wish to bring their furry friends along. Many accommodations also provide coffee and tea makers, ensuring guests can start their day with a warm beverage.
Can I find family house rentals in Gillespie Park?
In Gillespie Park, Florida, there are several family-friendly house rentals available, making it a suitable destination for those travelling with children. The neighbourhood features spacious homes that often include amenities such as fully equipped kitchens, ample living areas for relaxation, and outdoor spaces where kids can play safely. Many properties are conveniently located near local parks and recreational areas, allowing families easy access to outdoor activities.

Visitors can enjoy the nearby attractions, including the vibrant downtown area, which is filled with shops, restaurants, and cultural sites.
Can I rent a holiday home with a pool or hot tub in Gillespie Park?
In Gillespie Park, Florida, there are several holiday homes available for rent that feature both pools and hot tubs. This charming neighbourhood offers a relaxed atmosphere with easy access to local parks and attractions. Travellers can expect amenities such as private pools, inviting hot tubs, outdoor seating areas, and fully equipped kitchens, making these properties great for both relaxation and entertaining.
Are there any Gillespie Park holiday rentals with parking?
Vrbo offers a wide selection of holiday rentals in Gillespie Park with parking available—perfect for families or travellers 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.
Can I book pet-friendly holiday rentals in Gillespie Park?
In Gillespie Park, there are several pet-friendly holiday rentals available for those travelling with their furry companions. This charming neighbourhood in Florida offers a variety of accommodations, often featuring amenities such as private backyards, fully equipped kitchens, and spacious living areas that cater to both pets and their owners.

Travellers can expect to find properties with features like outdoor patios, where pets can enjoy fresh air, and easy access to nearby parks, making it convenient for walks and playtime. Additionally, the area is close to pet-friendly points of interest, including local parks that provide ample space for exercising pets and enjoying the outdoors.
Can I find long-stay holiday rentals in Gillespie Park?
A long-stay holiday rental in Gillespie Park is the best way to experience local living. Plus, you can make the most of long-stay discounts. Long-stay discounts are applied automatically when you enter your travel dates into the search tool, or you can use the "Weekly stay" and "Monthly stay" filters in your search.
When is the best time to visit Gillespie Park for a holiday rental?
The best time to visit Gillespie Park is during the peak season from January to March, with March being particularly popular among travellers seeking a sunny getaway. This period offers delightful temperatures averaging around 20 to 25 degrees Celsius, superb for enjoying outdoor activities such as picnicking in the park, exploring the nearby beaches, or taking leisurely strolls along the scenic trails.

During these months, Gillespie Park comes alive with visitors who appreciate the vibrant setting and abundant opportunities for recreation. Families, couples, and solo adventurers alike can relish the warm weather while participating in various activities, including kayaking or cycling through the picturesque surroundings.

For those looking for a more budget-friendly option, consider visiting in October. This month offers a quieter experience with fewer tourists, allowing you to enjoy the natural beauty of the park at a leisurely pace. The temperatures are still pleasant, making it a lovely time for nature walks and enjoying the local flora.

Ultimately, the best time for you to book a holiday rental in Gillespie Park will depend on your preference for lively crowds and activities or a peaceful retreat in the serene autumn months.
Are there any remote work holiday rentals in Gillespie Park?
In Gillespie Park, Florida, there are a variety of remote work holiday rentals available, with around 33 options to choose from. This area offers a vibrant setting, with nearby parks, cafes, and local shops that can enhance your work-life balance. Many of the rentals feature dedicated workspaces, such as desks and comfortable chairs, ensuring you have a productive environment. Additionally, high-speed Wi-Fi is commonly available, often included for free, allowing for seamless connectivity during your stay.

Gillespie Park itself is a delightful neighbourhood, where you can take breaks in the beautiful green spaces or explore the local amenities. The proximity to downtown Sarasota also means you can enjoy a lively cultural scene, with galleries, restaurants, and entertainment options close at hand. To help narrow your search, insert your dates and apply the "WiFi" filter on Vrbo.
How early should I book a Gillespie Park holiday rental?
Book your Gillespie Park holiday 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 holiday 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, Florida, United States of America?
In Gillespie Park, Florida, visitors can enjoy a range of attractions that highlight the area's charm. The park itself is a lovely green space, ideal for leisurely strolls, picnics, and community events. It features walking trails, playgrounds for children, and open areas that are great for outdoor activities.

Nearby, the vibrant neighbourhood of Sarasota offers cultural gems such as the Ringling Museum of Art, which showcases an impressive collection of artworks and the beautiful Ca' d'Zan mansion. The nearby Marie Selby Botanical Gardens is also a must-visit, featuring stunning tropical plants and serene walking paths.

For those interested in local dining and shopping, the downtown Sarasota area boasts numerous restaurants, cafes, and boutique shops, all within a short distance from Gillespie Park.
Can I change or cancel my Gillespie Park home rental booking on Vrbo?
To find Gillespie Park holiday 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 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 travellers 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 cosy cabin or a beach house, 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 holiday 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, such as last-minute cancellations, booking issues, or potential fraud, Vrbo customer service is available 24/7 to support you every step of the way.

Vrbo also offers support via live chat through our Help Centre, 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 organising 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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