Photo by Jay Mullenix

Historic Uptown holiday lettings

We found 230 holiday rentals — enter your dates for availability

Discover a selection of 6 homes and other holiday rentals in Historic Uptown that are perfect for your trip. Whether you’re staying in a holiday home with a group or just with your pet, you'll have the amenities that you expect and more, including Wi-Fi and parking. Whatever you're looking for, you'll find a property to rent to meet everyone's needs, including a place that's non-smoking or offers accessibility.

Find spaces that suit your style

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  • All the privacy of home

    Enjoy full kitchens, pools, gardens and more

  • More for less

    More space, more privacy, more amenities — more value

Why visit Historic Uptown

  • Historic allure: Discover the charming streets filled with history, offering a glimpse into St. Petersburg's rich past.
  • Outdoor activities: Enjoy beautiful parks and nearby beaches, perfect for picnics, strolls, and relaxation.
  • Cultural experiences: Explore fascinating art museums and local galleries that showcase vibrant creativity.
  • Unique shops and cafes: Browse quaint shops and indulge in delightful cafes that reflect the local culture.
  • Diverse accommodation: Choose from stylish townhouses, charming condos, and private holiday homes for a comfortable stay.

Popular types of accommodation around Historic Uptown

You've chosen to explore Historic Uptown, and now it's time to select your perfect accommodation. From stylish townhouses to charming condos and private holiday homes, there’s a delightful range of options to suit every taste. Whether you’re seeking the best hotels or unique apartments, Historic Uptown offers a variety of vacation rentals that combine comfort and character. Discover the ideal base for your adventure today!

  • Condos: The most sought-after accommodation in Historic Uptown, offering modern amenities and a community feel for an enjoyable stay.
  • Houses: A popular choice for groups or families, these homes provide a home-like environment with added privacy.
  • Apartments: A convenient option for travellers seeking a compact and practical living space in the heart of the area.
  • Cottages: Charming and quaint, these rentals offer a cosy retreat amidst the vibrant surroundings.
  • Villas: Luxurious and spacious, perfect for those wanting an upscale experience during their holiday.**

What do I need to keep in mind when booking a vacation around Historic Uptown

If you're planning a trip with a group, family, pets, or seeking extended stays, it's important to refine your search according to your specific needs. Here are some helpful booking tips for using Vrbo.

  • Traveling to Historic Uptown with a group: Think about how many bedrooms you'll require, as well as features like a fully equipped kitchen or outdoor space for group gatherings. Thankfully, you can easily filter for all these options and more on Vrbo.
  • Traveling to Historic Uptown with young kids: Travelling with young children can present its challenges. It’s important to prioritise their comfort and safety, along with suitable amenities like a private swimming pool. Additionally, considering your closeness to family-friendly attractions can enhance your experience.
  • Taking your pets with you to Historic Uptown: For many families, a holiday isn’t truly complete without their furry companions. If this resonates with you, take a look at Vrbo properties that welcome pets. Most pet-friendly accommodations offer feeding bowls and beds, ensuring that everyone feels comfortable and at home.
  • Planning for a long term stay visiting Historic Uptown: If you're in search of holiday rentals with 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. You might also want to include options such as a parking space, a well-equipped kitchen, or even a private pool in your search criteria.

Where to stay near Historic Uptown

Historic Uptown in St. Petersburg, Florida, offers a delightful blend of charm and history, making it an ideal destination for families and couples alike. With its picturesque streets, friendly atmosphere, and vibrant community, visitors can explore lovely parks, quaint cafes, and unique shops. Nearby attractions further enhance the experience, providing opportunities for scenic excursions and memorable moments in this beautiful neighbourhood. Discover the warmth and romance of Historic Uptown during your American holiday.

  • St. Petersburg - Clearwater: St. Petersburg - Clearwater is a vibrant metropolis located 559m from Historic Uptown. Renowned for its stunning beaches and outdoor activities, this area is perfect for families seeking fun and relaxation. Visitors can enjoy a leisurely day at the beach, explore the local shopping areas and mall centres, or stroll along the picturesque boardwalk. The nearby sandy shores provide an inviting environment for sunbathing and water sports, making it a top choice for those looking to experience Florida's coastal charm.
  • St. Petersburg: Situated just 621m away from Historic Uptown, St. Petersburg is a lively city known for its outdoor spaces and family-friendly attractions. Here, you'll find a range of shopping areas and luxurious resorts that cater to diverse tastes. Families can enjoy the local beaches, which offer ample opportunities for swimming and relaxing by the shore. The city’s beautiful parks and cultural venues also provide enriching experiences, ensuring that there's something for everyone in this welcoming destination.
  • St. Pete Beach: Located 4.3km from Historic Uptown, St. Pete Beach is a charming city that epitomises the quintessential beach holiday. Known for its stunning coastline, it attracts visitors seeking a fun-filled family experience amidst the sun and sand. The area boasts numerous resorts and shopping options, making it easy to unwind and shop for souvenirs. With its inviting beaches and vibrant neighbourhoods, St. Pete Beach is an ideal destination for those looking to enjoy the great outdoors while soaking in the relaxed Floridian atmosphere.

Vrbo Trips: Planning made easy

Vrbo's Trip Board provides a convenient platform for planning new trips, refining your existing arrangements, or managing your bookings. Your saved or booked properties are thoughtfully categorised into Potential, Upcoming, or Current Trips for easy access. To delve into Trip Boards, please visit: https://www.vrbo.com/en-gb/trips.

**Based on Vrbo properties bookings.

Frequently asked questions

What is the most popular type of holiday rental in Historic Uptown?
In Historic Uptown, holiday houses are the most popular type of rental, with around 31 available throughout the area. These homes often feature spacious layouts, multiple bedrooms, fully equipped kitchens, and outdoor spaces such as gardens or patios, making them ideal for families or groups. Additionally, there are approximately 29 apartments, which provide a more compact option with amenities like kitchenettes and communal areas for socialising. Several charming cottages can also be found, offering a quaint and cosy atmosphere.
Are there any beach house rentals in Historic Uptown?
In Historic Uptown, Florida, there are approximately 41 beach house rentals available, offering a charming coastal experience. These properties are typically located in picturesque neighbourhoods close to the waterfront, allowing easy access to local attractions. Most beach houses come with amenities such as fully equipped kitchens, spacious living areas, and outdoor decks or patios, great for enjoying the sunny Florida weather. Many rentals also feature private gardens and pools, making them ideal for families or groups looking for a relaxing retreat.
How much does it cost to rent a holiday home in Historic Uptown?
Prices for holiday rentals in Historic Uptown 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 Historic Uptown 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 Historic Uptown holiday house rentals?
You can find great discounts on house rentals in Historic Uptown 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.
Are there any Historic Uptown holiday rentals with parking?
Vrbo offers a wide selection of holiday rentals in Historic Uptown 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 find long-stay holiday rentals in Historic Uptown?
A long-stay holiday rental in Historic Uptown 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 Historic Uptown for a holiday rental?
April is the most popular time to visit Historic Uptown, as the vibrant atmosphere draws in visitors eager to experience the area's charm. The peak season runs from April to June, making it an ideal period for those looking to enjoy the delightful weather and engaging outdoor activities. With temperatures typically ranging from the mid to high 20s Celsius, this season is superb for leisurely strolls along the picturesque streets, enjoying the numerous parks, and exploring the local art scene.

April stands out not only for its pleasant climate but also for the lively events that unfold throughout the month. Visitors will find themselves immersed in local culture, with various festivals and art exhibitions showcasing the community's creativity. This is an excellent opportunity to enjoy the fresh air while taking in the sights and sounds of Historic Uptown.

For those considering a more budget-friendly option, October presents a lovely alternative. While it's outside the peak season, you can still enjoy the pleasant weather and the beauty of the changing leaves, all while experiencing a quieter side of the area. This month is superb for those who appreciate a more relaxed atmosphere and fewer crowds.
Are there any remote work holiday rentals in Historic Uptown?
In Historic Uptown, Florida, there are a variety of remote work holiday rentals available, with around 46 properties suiting this need. Travellers can expect accommodations equipped with essential amenities for a productive work environment, such as desks, ergonomic chairs, and computer monitors. High-speed Wi-Fi is commonly available, ensuring a seamless online experience. Many properties also include safes for securing personal belongings, alongside comfortable living spaces that allow for relaxation after work hours. To help narrow your search, insert your dates and apply the "WiFi" filter on Vrbo.
How early should I book a Historic Uptown holiday rental?
Book your Historic Uptown 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 Historic Uptown?
In Historic Uptown, Florida, visitors can enjoy a variety of attractions that highlight the area's charm and community spirit. The neighbourhood is known for its beautiful tree-lined streets and historic architecture, making it ideal for leisurely strolls. One of the main draws is the picturesque Crescent Lake Park, which offers walking trails, picnic areas, and a serene lake for birdwatching.
Can I change or cancel my Historic Uptown home rental booking on Vrbo?
To find Historic Uptown 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 Historic Uptown 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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