Photo by Dee Val

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.

Holiday rentals with weekly discounts – Uptown

Showing deals for:11 Dec - 18 Dec

Harbor at Lions Bridge
Front porch in evening
Living Room
Dining Room
Exceptional
(116 reviews)

Perfect wedding/beach/golf retreat

St. Augustine

8% off
£3,064
for 7 nights, 1 home
£438 per night
includes taxes & fees
Perfect wedding/beach/golf retreat
Interior
Interior
Private kitchen
Dining
Exceptional
(18 reviews)

Charming Home and Cottage in Downtown St Augustine for 14

St. Augustine

8% off
£5,634
for 7 nights, 1 home
£805 per night
includes taxes & fees
Charming Home and Cottage in Downtown St Augustine for 14
Living area
Outdoor dining
Dining
Interior
Exceptional
(54 reviews)

Ancient City Cottage

St. Augustine

7% off
£985
for 7 nights, 1 cottage
£141 per night
includes taxes & fees
Ancient City Cottage
Interior
Private entrance in cute area off San Marco
Interior
Interior
Exceptional
(33 reviews)

Close proximity to Vilano and St George

St. Augustine

8% off
£725
for 7 nights, 1 apartment
£104 per night
includes taxes & fees
Close proximity to Vilano and St George
Property grounds
Exterior
Living area
Room
Exceptional
(48 reviews)

Historic Full House 2min walk to Historic Downtown with 75" 8K TV & Gas Grill

St. Augustine

8% off
£3,040
for 7 nights, 1 home
£434 per night
includes taxes & fees
Historic Full House 2min walk to Historic Downtown with 75" 8K TV & Gas Grill
Exterior detail
Private kitchen
Terrace/patio
Living area
Exceptional
(8 reviews)

Riberia Retreat - Team Joseph Ellen

St. Augustine

7% off
£2,983
for 7 nights, 1 room
£426 per night
includes taxes & fees
Riberia Retreat - Team Joseph Ellen
Lots of closets in bedroom 1
Living room also provides desk and chair in well lit alcove
Living room leading to patio
Exterior of Casa de Flora II
Exceptional
(157 reviews)

Relaxed Elegance at Casa de Flora II in historic St Augustine, Florida 🚭

St. Augustine

8% off
£1,429
for 7 nights, 1 home
£204 per night
includes taxes & fees
Relaxed Elegance at Casa de Flora II in historic St Augustine, Florida 🚭
Historic Details Meet Modern Comfort
Kitchen Island with Comfy Seating
Spacious king suite with ensuite bath and natural light
Fully Equipped Kitchen & Laundry
Exceptional
(12 reviews)

Chic+Eco Friendly! Chefs Kitchen•Quick Walk to Old City and Public Park!

St. Augustine

8% off
£5,004
for 7 nights, 1 home
£715 per night
includes taxes & fees
Chic+Eco Friendly! Chefs Kitchen•Quick Walk to Old City and Public Park!
Outdoor dining
Living area
Room
Private kitchen
Exceptional
(24 reviews)

Cozy Uptown Guest House

St. Augustine

7% off
£2,009
for 7 nights, 1 apartment
£287 per night
includes taxes & fees
Cozy Uptown Guest House
Living dining room.
Flagler College - 5 min on foot and you are there
View of Property - Apartment 2 is the building in view right, downstairs patio
Full kitchen
Exceptional
(239 reviews)

C2 Perfect location in historic city center, near beaches, patio, free parking!

St. Augustine

8% off
£1,178
for 7 nights, 1 apartment
£168 per night
includes taxes & fees
C2 Perfect location in historic city center, near beaches, patio, free parking!
Back bedroom closet with cozy robes, extra linens, blanket, and iron
Sunroom with comfortable seating for four with blinds for sun glare & privacy
Front staircase is to the right and leads  to apartment C into the sunroom
Beautiful sunroom facing San Marco Avenue
Exceptional
(48 reviews)

Luxurious and Relaxing Elegance Upstairs 🚭

St. Augustine

8% off
£1,537
for 7 nights, 1 apartment
£220 per night
includes taxes & fees
Luxurious and Relaxing Elegance Upstairs 🚭
Artwork in the sunroom
Enjoy a meal, a book or listening to music in this beautiful relaxing sunroom.
Sliding bathroom door for privacy.
Local art
Exceptional
(27 reviews)

132A Relaxed Luxury at Casa de Flora in St Augustine

St. Augustine

8% off
£1,261
for 7 nights, 1 apartment
£180 per night
includes taxes & fees
132A Relaxed Luxury at Casa de Flora in St Augustine
Million dollar view
Community swimming pool with Bathrooms
Large extended balcony
kitchen pass through
Exceptional
(23 reviews)

Saint Augustine Million Dollar water view and minutes to all local Beaches

St. Augustine

8% off
£1,374
for 7 nights, 1 apartment
£196 per night
includes taxes & fees
Saint Augustine Million Dollar water view and minutes to all local Beaches
Interior
Pool
Exterior
Terrace/patio
Exceptional
(65 reviews)

The Gaudi House- Pool/Minutes to DNTN and Beach

St. Augustine

7% off
£4,317
for 7 nights, 1 home
£617 per night
includes taxes & fees
The Gaudi House- Pool/Minutes to DNTN and Beach
4 parking spaces available in the back. EV Charger is also available. Plug type nema 14-50.
Outdoor dining
Exterior detail
Interior
Very good
(36 reviews)

Walking distance to St George, packed with attractions and activities!

St. Augustine

8% off
£804
for 7 nights, 1 apartment
£115 per night
includes taxes & fees
Walking distance to St George, packed with attractions and activities!
  • Peace of mind

    Our Book with Confidence Guarantee gives you 24/7 support
  • More quality time

    From booking to staying, the whole process is simple and enjoyable
  • All the privacy of home

    Enjoy full kitchens, pools, gardens and more
  • More for less

    More 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.