Uptown vacation rentals
We found 450 vacation rentals — enter your dates for availability
Discover a selection of 124 homes, 44 apartments, and other vacation rentals in Uptown that are perfect for your trip. Whether you're staying in a vacation rental with family or friends, you'll have the amenities you expect and more, which might include a pool and a washer and dryer. You're sure to find a rental that has what everyone needs, including options that are accessible or non-smoking.
Holiday rentals with weekly discounts - Uptown
Showing deals for:Nov 13 - Nov 20

Exceptional
(18 reviews)
Magnolia Ave Peacock House Fountain of Youth, 4 min to beach & Downtown
St. Augustine
CA $402
CA $3,705 total

Exceptional
(115 reviews)
Perfect wedding/beach/golf retreat
St. Augustine
CA $466
CA $4,249 total

Exceptional
(8 reviews)
Charming Victorian Home in beautiful St. Augustine with WiFi, AC
St. Augustine
CA $343
CA $3,326 total

Exceptional
(76 reviews)
Luxe Lemon Loft in Historic Downtown St Aug
St. Augustine
CA $168
CA $1,546 total

Exceptional
(116 reviews)
Three Bedroom, Sanitized, Pet Friendly Bungalow
St. Augustine
CA $273
CA $2,540 total

Exceptional
(157 reviews)
Relaxed Elegance at Casa de Flora II in historic St Augustine, Florida 🚭
St. Augustine
CA $248
CA $2,294 total

Exceptional
(63 reviews)
Cozy cottage in a cute neighborhood with parking, close to historic downtown!
St. Augustine
CA $133
CA $1,335 total

Wonderful
(85 reviews)
DOWNTOWN COZY APARTMENT
St. Augustine
CA $154
CA $1,356 total

Exceptional
(27 reviews)
132A Relaxed Luxury at Casa de Flora in St Augustine
St. Augustine
CA $230
CA $2,098 total

Exceptional
(47 reviews)
Luxurious and Relaxing Elegance Upstairs 🚭
St. Augustine
CA $259
CA $2,342 total

Exceptional
(79 reviews)
💲Romantic Renovated Secret Garden💲 Marble Floors & Bath – DT Just Half Mile - Beach Only 3
St. Augustine
CA $250
CA $2,324 total

Wonderful
(474 reviews)
The Red Cottage ~ 5 min. stroll to Historic St. George Street - on site parking
St. Augustine
CA $168
CA $1,508 total

Exceptional
(55 reviews)
Oasis, 1-bedroom Apt. walk to all of downtown St. Augustine with WiFi, AC
St. Augustine
CA $147
CA $1,292 total

Exceptional
(83 reviews)
COMFY DOWNTOWN SPACE
St. Augustine
CA $147
CA $1,290 total

Exceptional
(162 reviews)
Perfect Location! Situated In The Eclectic Uptown Area.
St. Augustine
CA $146
CA $1,289 total

Exceptional
(239 reviews)
C2 Perfect location in historic city center, near beaches, patio, free parking!
St. Augustine
CA $185
CA $1,716 total

Exceptional
(54 reviews)
💲Grand Oak - Renovated 1885 Queen Anne - 1 Block Stroll to Historic DT - Beach only 3 Mi💲
St. Augustine
CA $225
CA $2,111 total

Exceptional
(87 reviews)
The ArtHouse: Where Industrial Charm Meets Creative Inspiration
St. Augustine
CA $338
CA $3,079 total

Exceptional
(79 reviews)
Old town historic home
St. Augustine
CA $192
CA $1,826 total

Exceptional
(47 reviews)
Adorable Uptown Cottage-Steps to attractions! Perfect for families and couples!
St. Augustine
CA $278
CA $2,599 total

Exceptional
(5 reviews)
Apothecary - Upper Unit Downtown 2BR
St. Augustine
CA $186
CA $1,732 total

Exceptional
(36 reviews)
Downtown Lodge-Clean-Pet Friendly-Free Parking
St. Augustine
CA $221
CA $2,017 total
Find spaces that suit your style
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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

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

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

Historic District Dream - 3 BR Beautiful Bungalow! Walk to All Attractions!
Sleeps 5 · 3 bedrooms · 1 bathroom

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

Charming Victorian Home in beautiful St. Augustine with WiFi, AC
Sleeps 8 · 3 bedrooms · 2 bathrooms

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

Lovely
This property is adorable! Check in was seamless, clean like it’s a new build and beautifully decorated! The bonus of snacks drinks and fresh baked cookies was a sweet surprise! We will stay here again next time we are in St Augustine!
Wendy M.
Stayed Mar 2024

1st trip to St Augustine
Perfect location to get to everything and everywhere. Host was quick to respond to questions before booking and prior to our arrival. Peaceful, friendly and beautiful neighbourhood. So many nice touches and helpful things/supplies for travelers. Definitely return to this rental next visit to St Augustine.
Lisa C.
Stayed Feb 2024

Fatastic location and decor!
This listing is the most thoughtfully decorated and stocked rental I have ever stayed in. The owner was fantastic to deal with, very friendly, and very accomodating. The location is a five minute walk to historic downtown St. Augustine. I would stay here again in a heartbeat. I can't recommend it enough!
Sandra R.
Stayed Mar 2023
Frequently asked questions
How much does it cost to rent a vacation home in Uptown?
Prices for vacation 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 travelling 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.
Are there any discounts for Uptown vacation 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 vacation rentals with parking?
Vrbo offers a wide selection of vacation 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 vacation rentals in Uptown?
A long-stay vacation 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 vacation rental?
The peak travel season in Uptown, Florida, runs from May to July, making it the ideal time for those seeking vibrant vacation 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 vacation 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 vacation rental?
Book your 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 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 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 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 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.
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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