Historic Uptown vacation rentals

We found 227 vacation rentals — enter your dates for availability

Welcome to St. Petersburg, where rich history meets stunning waterfront views and vibrant outdoor spaces. Stroll along picturesque shores, explore charming cafes, and immerse yourself in family-friendly events that cater to all ages. Nestled in Historic Uptown, our vacation rentals offer stylish townhouses and cozy condos, perfect for groups seeking comfort and convenience. Enjoy essential amenities and the spaciousness of a home-like experience, making your getaway truly unforgettable.

Holiday rentals with weekly discounts - Historic Uptown

Showing deals for:Nov 6 - Nov 13

Smart TV to use in Livingroom with any apps you may need like Netflix or amazon or apple
The house
Entrance To Peacock
patio for relaxing
Exceptional
(60 reviews)

Close to all with a King-bed! Bikes included

St. Petersburg

8% off
$151
$1,060 for 7 nights
All fees included
Close to all with a King-bed! Bikes included
Dining
Relaxing Saltwater Lagoon
Enjoy a day at the beach just 8 mile drive away!
Living area
Exceptional
(42 reviews)

Rays Game! Queen W/Pool & Blocks 2 Dtwn w/2 Bikes

St. Petersburg

9% off
$148
$1,038 for 7 nights
All fees included
Rays Game! Queen W/Pool & Blocks 2 Dtwn w/2 Bikes
Living area
Living area
Miscellaneous
Interior
Exceptional
(55 reviews)

Hello Dali Our Playful Art-Inspired Upstairs Apartment Near Downtown Walkable

St. Petersburg

8% off
$168
$1,175 for 7 nights
All fees included
Hello Dali Our Playful Art-Inspired Upstairs Apartment Near Downtown Walkable
Private kitchen
Interior
Dining
Room
Exceptional
(50 reviews)

Crescent Heights Cottage - Fully stocked - short or long term extended stays!

St. Petersburg

8% off
$129
$905 for 7 nights
All fees included
Crescent Heights Cottage - Fully stocked - short or long term extended stays!
Stovetop counter with coffee and double oven and microwave
On a main road, but the fenced yard/courtyard feels tucked away
Livingroom with seating and reading area and stairs to 2nd level
Master king with smart tv
Exceptional
(21 reviews)

4BR Historic Home Near Downtown | Pool & Courtyard

St. Petersburg

8% off
$476
$3,329 for 7 nights
All fees included
4BR Historic Home Near Downtown | Pool & Courtyard
Coffee station for your use
Entrance to Hideaway
Pool to onsite guests on property
Bar area looking into Kitchen
Exceptional
(42 reviews)

Explore St. Pete! Bikes Included, Prime Spot

St. Petersburg

8% off
$188
$1,315 for 7 nights
All fees included
Explore St. Pete! Bikes Included, Prime Spot
Stairs to 2nd story rental - entire floor and entrance are yours
Lagoon Cocktail Pool in Courtyard
Shared Small saltwater Backyard Lagoon to relax in
Treehouse Rental upstairs patio
Exceptional
(42 reviews)

Hidden Oasis Guest Apt+Kg Bd 2bikes/close DT

St. Petersburg

9% off
$174
$1,219 for 7 nights
All fees included
Hidden Oasis Guest Apt+Kg Bd 2bikes/close DT

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Find out more about Historic Uptown

Why visit Historic Uptown

  • Historic Homes: Stroll through charming streets lined with beautifully preserved historic homes, showcasing stunning architecture.
  • Cultural Experiences: Engage in local neighborhood gatherings and explore vibrant art museums that celebrate the area's rich culture.
  • Outdoor Activities: Enjoy family-friendly outdoor activities in urban parks and nearby beaches, perfect for relaxation and fun.
  • Scenic Waterfront: Venture to Downtown St. Petersburg for breathtaking waterfront views and vibrant cultural experiences.
  • Diverse Accommodations: Choose from stylish bungalows, modern condos, or cozy vacation homes for a unique stay.

Popular types of accommodation around Historic Uptown

Planning a getaway to Historic Uptown? You're in for a treat. Discover a variety of stylish accommodations, from charming bungalows to modern condos and houses. Whether you're looking for a cozy townhouse on Volkers St. or a sleek apartment in downtown Palm Harbor, you'll find the perfect spot for your stay. Explore your options and enjoy the unique character Historic Uptown has to offer.

  • Condos: The top choice for vacationers in Historic Uptown, offering modern amenities and convenient locations.
  • Houses: A popular option for families and groups seeking spacious and comfortable accommodations.
  • Apartments: Ideal for solo travelers or couples, these rentals provide a cozy and convenient stay.
  • Cottages: Charming and quaint, cottages are perfect for those looking for a homey feel during their getaway.
  • Villas: For a luxurious experience, villas offer upscale living with plenty of space and style.**

Top attractions near Historic Uptown

Historic Uptown in St. Petersburg, Florida, is perfect for outdoor family vacations, offering a blend of beach, urban parks, and art museums. Explore the charm of historic homes and engage in neighborhood gatherings while soaking in the cultural experiences this vibrant area has to offer. Don't miss the allure of the historic architecture and the beautiful surroundings that make this destination a must-visit for any traveler.

  • Tampa Bay: A stunning bay known for its picturesque beaches and outdoor scenery, perfect for relaxing strolls, water sports, and enjoying Florida's natural beauty, located 7 miles from Historic Uptown.
  • Salvador Dali Museum: This art museum is a cultural gem, housing an extensive collection of works by the surrealist master Salvador Dali, just 2 miles away, offering a unique insight into his imaginative world.
  • Vinoy Park: An urban park that combines family-friendly activities with outdoor enjoyment, featuring lush landscapes and beautiful views of the city, located 2 miles from Historic Uptown.

Things to do recommended for couples

For a romantic getaway in Historic Uptown, enjoy a lively concert at Jannus Live, just a mile away, or immerse yourselves in dance at St. Pete's Historic Coliseum, 0.7 miles away. Finally, savor a romantic dinner at 400 Beach, also a mile away, overlooking the city.

Things to do recommended for families

Families can catch a game at Tropicana Field, just 0.9 miles away, enjoy wellness at Maximo Park, 5 miles away, or experience adventure at Tampa Bay Grand Prix, located 8 miles away. Each destination offers a unique vibe for a memorable family outing.

Things to do recommended for groups

Groups visiting Historic Uptown can enjoy shopping and entertainment at John's Pass Village & Boardwalk, immerse themselves in culture at the Mahaffey Theater, or play a round of golf at the Renaissance Vinoy Golf Club, all within a short distance of the area.

*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 Historic Uptown

If you're traveling with a group, enjoying a family getaway, bringing along your pets, or planning an extended stay, be sure to prioritize your filters accordingly. Here are some helpful Vrbo booking tips for you.

  • Traveling to Historic Uptown with a group: Think about how many bedrooms you'll require, as well as any amenities you might want, like a fully equipped kitchen or outdoor space for gatherings. Thankfully, you can easily filter for these features and more on Vrbo.
  • Traveling to Historic Uptown with young kids: Traveling with little ones can be quite a task. It's important to prioritize their comfort and safety, along with providing 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 Historic Uptown: For many families, a vacation isn't truly enjoyable without their furry companion by their side. If you can relate to this, explore Vrbo listings that welcome pets. Many of these 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 seeking vacation rentals that offer discounts for stays of a month or more, you've come to the right spot. By using the appropriate filter, you can effortlessly discover and save on monthly rentals. Don't forget to include amenities like a parking space, a well-equipped kitchen, or a private pool in your search as well.

Where to stay near Historic Uptown

Historic Uptown in St. Petersburg, Florida, offers a delightful blend of outdoor activities and family-friendly exploration. Stroll through charming streets lined with historic homes, or venture to Downtown St. Petersburg for vibrant culture and scenic waterfront views. This welcoming neighborhood is perfect for romantic outings and exciting excursions, making it an ideal spot for travelers seeking a memorable vacation experience.

  • St. Petersburg - Clearwater: St. Petersburg - Clearwater is a vibrant metropolis that perfectly blends urban living with breathtaking coastal scenery. Located in the heart of Pinellas County, this area offers a wealth of experiences for travelers seeking outdoor adventures and family-friendly activities. Visitors can explore the area's beautiful beaches, bustling shopping districts, and scenic boardwalks. With attractions like the famous Clearwater Beach and local parks, it’s an ideal destination for those looking to unwind under the sun while enjoying a variety of recreational opportunities.
  • St. Petersburg: St. Petersburg is a charming city known for its stunning waterfront parks and rich cultural scene. Nestled in the heart of the Tampa Bay area, St. Petersburg offers visitors a delightful mix of outdoor activities and urban excitement. The city is home to a plethora of shopping areas and resorts, along with attractions like the Salvador Dalí Museum and the picturesque Vinoy Park. Families will love the local beaches and community events that highlight the vibrant culture and friendly atmosphere of this beautiful city.
  • St. Pete Beach: Located just 7 miles from Historic Uptown, St. Pete Beach is a sun-soaked paradise famous for its pristine coastline and family-oriented atmosphere. This lively beach city attracts visitors looking for relaxation and outdoor fun, with activities ranging from water sports to leisurely strolls along the shore. The area boasts a variety of resorts and shopping options, making it a fantastic spot for both adventure seekers and those wanting to kick back and enjoy the stunning views. Families can enjoy the welcoming ambiance and numerous beachside attractions, ensuring a memorable vacation experience.

Best time to go to Historic Uptown

If you're planning a trip to Historic Uptown, it's a good idea to check both the weather and property rates. The warmest month is August. Peak season runs in February to March and July, while off-peak times, like September to November tend to have fewer bookings and better deals.

calendarCalendar MonthtemperatureTemperaturerainPrecipitationmostlyCloudinessoccupationOccupancypricePricing
January61.3°F (16.3°C)Light RainMostly SunnyAverageSlightly Low
February64.6°F (18.1°C)No Rain (Dry)Mostly SunnyModerately HighAverage
March67.8°F (19.9°C)Light RainMostly SunnyModerately HighSlightly High
April73.6°F (23.1°C)Light RainMostly SunnyAverageSlightly High
May78.3°F (25.7°C)Light RainSunnyAverageAverage
June82.0°F (27.8°C)Light RainMostly SunnyAverageAverage
July83.3°F (28.5°C)Moderate RainMostly SunnyModerately HighSlightly High
August83.7°F (28.7°C)Light RainMostly SunnyAverageAverage
September81.5°F (27.5°C)Light RainMostly SunnyModerately LowSlightly Low
October76.6°F (24.8°C)Light RainMostly SunnyModerately LowSlightly Low
November69.6°F (20.9°C)No Rain (Dry)Mostly SunnyModerately LowAverage
December65.5°F (18.6°C)Light RainMostly SunnyAverageAverage

Booking with Vrbo is a breeze

Are you eager to save on your upcoming journey? Keep in mind that being flexible with your travel dates can lead to significant savings, as prices can vary. Additionally, opting for a longer stay often results in even greater discounts. To discover the perfect Vrbo rental that fits your budget, take advantage of our filters to sort by price, location, and type of vacation property. We're here to help you find the best deal.

Vrbo Trips: Planning as easy as it gets

Vrbo's Trip Board offers a user-friendly platform where you can effortlessly create new trips, continue planning from where you paused, or easily view and manage your itinerary. You’ll see the properties you’ve saved or booked neatly organized into categories: Potential, Upcoming, or Current Trips. To begin exploring 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 Historic Uptown?
In Historic Uptown, apartments are the most popular type of vacation rental, with about 32 available throughout the area. These apartments are typically situated in charming neighborhoods, offering a blend of comfort and convenience. Travelers can expect amenities such as fully equipped kitchens, cozy living areas, and often outdoor spaces like balconies or patios, superb for enjoying the pleasant Florida weather. For those seeking more space, there are around 24 vacation houses available, which cater well to families or larger groups. These homes generally feature multiple bedrooms, private yards, and ample living space, making them ideal for gatherings.
Are there any beach house rentals in Historic Uptown?
In Historic Uptown, there are about 41 beach house rentals available, primarily located near the waterfront and charming neighborhoods. These rentals typically feature spacious living areas, multiple bedrooms, and fully equipped kitchens, making them suitable for families or groups. Many properties also include outdoor spaces such as patios or gardens, great for enjoying the Florida sunshine.
How much does it cost to rent a vacation home in Historic Uptown?
Prices for vacation 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 vacation 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.
What are popular rental amenities in Historic Uptown?
In Historic Uptown, travelers can expect a range of popular rental amenities that enhance their stay. Most vacation rentals feature fully equipped kitchens, allowing guests to prepare their own meals and enjoy dining at their leisure. Many properties also include outdoor spaces such as decks or patios, superb for relaxing or entertaining in the pleasant Florida weather. Onsite parking is commonly available, providing convenience for those who may have a vehicle. Additionally, travelers will find amenities like coffee and tea makers for a quick morning pick-me-up, and desks that cater to those who may need to catch up on work or planning during their stay.
Can I find family house rentals in Historic Uptown?
In Historic Uptown, Florida, there are numerous family-friendly house rentals available—around 22 to choose from. This charming neighborhood is known for its vibrant setting and historic architecture, making it an appealing destination for families. Many of these homes offer spacious living areas, fully equipped kitchens for preparing family meals, and outdoor spaces where children can play safely.Visitors can enjoy amenities like Wi-Fi, air conditioning, and laundry facilities, ensuring a comfortable stay. The area is close to parks and recreational spots, allowing families to explore nature while enjoying activities such as picnicking or biking.
Can I rent a vacation home with a pool or hot tub in Historic Uptown?
In Historic Uptown, Florida, there are several vacation homes available for rent that feature both pools and hot tubs. This charming neighborhood is known for its picturesque streets and historic architecture, providing a lovely backdrop for your stay. Travelers can expect amenities such as private pools for relaxation and entertainment, along with hot tubs that offer a superb way to unwind after a day of exploring. Many properties also come equipped with fully stocked kitchens, spacious living areas, and outdoor spaces, making them ideal for families or groups seeking a comfortable getaway.
Are there any Historic Uptown vacation rentals with parking?
Vrbo offers a wide selection of vacation rentals in Historic Uptown 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.
Can I book pet-friendly vacation rentals in Historic Uptown?
In Historic Uptown, travelers can find a variety of pet-friendly vacation rentals, with around 19 options available. This charming neighborhood offers a mix of accommodations that cater to pet owners, featuring amenities such as spacious backyards, pet-friendly furnishings, and easy access to outdoor spaces where pets can roam. Many rentals come with modern kitchens, comfortable living areas, and outdoor patios, superb for relaxing after a day of exploring.The neighborhood itself is known for its beautiful parks and tree-lined streets, providing ample opportunities for walks with your furry companions. Nearby, you'll find places like the scenic Crescent Lake Park, which features walking paths and open green spaces, ideal for pets and their owners to enjoy together.
Can I find long-stay vacation rentals in Historic Uptown?
A long-stay vacation rental in Historic Uptown 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 Historic Uptown for a vacation rental?
April marks the beginning of peak season in Historic Uptown, attracting visitors eager to enjoy its vibrant setting and rich history. This month is particularly special, as the weather is warm and pleasant, typically ranging from the mid-60s to the low 80s Fahrenheit. With blooming gardens and outdoor festivals, April sets the stage for a delightful vacation experience.As you explore Historic Uptown, you'll find plenty of opportunities for leisurely strolls along scenic streets lined with historic architecture, charming boutiques, and inviting cafes. The area's parks and waterfront are great for picnicking or simply soaking in the sun, making it an ideal time for outdoor activities and sightseeing.If you're looking for a more budget-friendly option, consider visiting in October. During this month, you can still enjoy mild weather while experiencing a more relaxed atmosphere, allowing for peaceful walks and a chance to connect with the local culture without the crowds.Ultimately, the best time to visit Historic Uptown really depends on your preferences.
Are there any remote work vacation rentals in Historic Uptown?
In Historic Uptown, Florida, there are around 50 vacation rentals suitable for remote work. This vibrant neighborhood is known for its charming architecture and a variety of local amenities, making it an ideal spot for those looking to blend work and leisure. Many of these rentals are equipped with dedicated workspaces, including desks and ergonomic chairs, as well as high-speed Wi-Fi and additional technology like computer monitors. This setup ensures a comfortable and productive work environment.Travelers can also enjoy the neighborhood's rich cultural scene, with nearby parks, coffee shops, and restaurants, providing opportunities for breaks and relaxation. To help narrow your search, insert your dates and apply the "WiFi" filter on Vrbo.
How early should I book a Historic Uptown vacation rental?
Book your Historic Uptown 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 Historic Uptown, Florida, United States of America?
In Historic Uptown, Florida, visitors can explore a variety of attractions that showcase the area's rich history and vibrant culture. The neighborhood is known for its beautiful historic homes and tree-lined streets, making it a picturesque area for leisurely walks. One of the key highlights is the Museum of Fine Arts, which features a diverse collection of art and frequently hosts special exhibitions.Nearby, the Sunken Gardens offers a serene escape with its lush tropical plants and stunning botanical displays, great for nature lovers and those seeking a tranquil environment. The area also boasts several parks, such as Williams Park, where visitors can enjoy outdoor activities and community events.
Can I change or cancel my Historic Uptown home rental booking on Vrbo?
To find Historic Uptown 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 Historic Uptown 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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