Uptown holiday lettings
We found 456 holiday rentals — enter your dates for availability
Discover a selection of 123 homes, 45 apartments and other holiday rentals in Uptown that are perfect for your trip. Whether you're staying in a holiday rental with your children and pets or just with friends, you'll find the amenities that you need and want, which might include parking and a hot tub. You'll be able to choose a property to rent that has what everyone needs, including options that are accessible or non-smoking.
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Find properties near top attractions in Uptown

St Augustine Antique Emporium
More information about St Augustine Antique Emporium. Opens in a new window.Find the best place to stay - Uptown

Stay Downtown St. Augustine 3BR and Parking
Sleeps 10 · 3 bedrooms · 3 bathrooms

Minutes away from the beach and walking distance into town
Sleeps 5 · 3 bedrooms · 2 bathrooms

Walker House c1888-Nat'l Reg of Historic Places
Sleeps 6 · 3 bedrooms · 3 bathrooms

Oak Canopy Escape - St Augustine, Heated Pool
Sleeps 6 · 3 bedrooms · 2 bathrooms

Historic! Walk to Downtown Attractions and Restaurants! Courtyard, Parking, $300 in Free Tickets!
Sleeps 4 · 2 bedrooms · 1+ bathroom

Adorable Uptown Cottage-Steps to attractions! Perfect for families and couples!
Sleeps 6 · 3 bedrooms · 2 bathrooms
Top rated rentals - Uptown

Fantastic quite cottage on waters edge
This was one of the best equipped cottages I’ve stayed in. It’s in a great location on the waters edge and within walking distance of all the attractions and restaurants.
It was also very peaceful.
Suzanne S.
Stayed Apr 2024

Unique and Welcoming!
There were no surprises - everything was as advertised. There were many little extras: hairdryer; toiletries (extra toothbrushes, shampoo; welcome wine bottle; candies; new Weber grille, etc. ).
Beds and pillows were very comfortable!
The home was beautifully unique in its decor which reminded us they we were on vacation.
Dave and Wendy were very responsive to our questions. We would highly recommend this home for your visit to St. Augustine as it is in walking distance to many attractions.
Ann H.
Ann H.
Stayed Feb 2020

Beautiful and peaceful place.
Visited this lovely place with family recently and enjoyed every minute from start to finish. Pauline was very helpful and the house had all you could need. Very clean, cared for and comfortable property. My girls loved the pool and we all felt very safe and secure. We will definitely be back next Easter.
Chris S.
Stayed Apr 2017
- Peace of mindOur Book with Confidence Guarantee gives you 24/7 support
- More quality timeFrom booking to staying, the whole process is simple and enjoyable
- All the privacy of homeEnjoy full kitchens, pools, gardens and more
- More for lessMore space, more privacy, more amenities — more value
Frequently asked questions
How much does it cost to rent a holiday home in Uptown?
Prices for holiday rentals in 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 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 Uptown holiday house rentals?
You can find great discounts on house rentals in 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 Uptown holiday rentals with parking?
Vrbo offers a wide selection of holiday rentals in 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 Uptown?
A long-stay holiday rental in 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 Uptown for a holiday rental?
The peak travel season in Uptown, Florida, runs from May to July, making it the ideal time for those seeking vibrant holiday experiences filled with sunshine and outdoor activities. July stands out as the most popular month, attracting visitors eager to enjoy the warm weather, local festivals, and the lively option that characterises this time of year.During these summer months, you can expect temperatures to hover around the mid to high 30s Celsius, superb for sun-soaked days at the beach or exploring the area's parks and recreational facilities. The bustling community vibe is complemented by numerous events and attractions, ensuring that there's always something happening nearby.For those looking for a more budget-friendly option, consider planning your visit in October. This month allows you to enjoy the charm of Uptown with fewer crowds, making it a great time for leisurely strolls and the chance to appreciate the local culture at a more relaxed pace. The weather remains pleasantly warm, with temperatures typically in the low to mid-30s Celsius, making outdoor activities still very enjoyable.Ultimately, the best time to visit Uptown for a holiday rental depends on your preferences—whether you thrive in the lively option of peak season or prefer the quieter charm of the shoulder months.
How early should I book a Uptown holiday rental?
Book your 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 Uptown, Florida, United States of America?
In Uptown, Florida, visitors can enjoy a variety of attractions that highlight the area's charm and vibrancy. One popular spot is the Uptown Art Gallery, which showcases local artwork and often hosts community events. The nearby Fort Lauderdale Beach offers a beautiful stretch of sand for sunbathing and water activities, making it a great destination for beach lovers.For those interested in shopping and dining, the area has several upscale boutiques and trendy restaurants that cater to a diverse palate. Additionally, the lush landscapes of the local parks provide opportunities for outdoor activities, including walking trails and picnic areas.
Can I change or cancel my Uptown home rental booking on Vrbo?
To find 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 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.

