Uptown holiday rentals

We found 396 holiday rentals — enter your dates for availability

Discover a selection of 121 homes, 38 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:20 Feb - 27 Feb

Image gallery for The Red Cottage ~ 5 min. stroll to Historic St. George Street - on site parking

Terrace/patio
9.0 out of 10, Wonderful, (432 reviews)
Wonderful
(432 reviews)

The Red Cottage ~ 5 min. stroll to Historic St. George Street - on site parking

St. Augustine, FL

8% off
Price is S$1,238
for 7 nights, 1 cottage
S$177 per night
includes taxes & fees
The Red Cottage ~ 5 min. stroll to Historic St. George Street - on site parking

Find spaces that suit your style

  • 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, laundry, 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 rental in Uptown?
Season, property type and length of stay are some of the things that can affect the price of a holiday home. Simply add your dates of travel to find your ideal fit. From quaint country cottages to sprawling luxury villas, all Vrbo holiday rentals offer amazing value.
How much does it cost to rent a beach house in Uptown?
When you travel and the style and size of the property will influence the cost of your beachside holiday rental. Put in your Uptown travel dates to view your available options on Vrbo. Looking for a backyard so the kids can run around, or a pool to keep them busy? Use our filters to pick the features and amenities you want.
What are the top attractions for families in Uptown?
Keep the kids occupied at these popular family-friendly attractions in Uptown:

  • St. Augustine Beach
  • Vilano Beach
  • St. Augustine Alligator Farm Zoological Park

How old do you have to be to rent a holiday rental in Uptown?
The minimum age allowed can vary across properties on Vrbo, so check the rules of the holiday home in Uptown you want to book. But in general, it's 16, 18 or 21.
How long can I rent a holiday rental in Uptown for?
How long you can book a holiday rental in Uptown differs according to the property. Simply enter your desired dates to display a list of options offering extended stays. With plenty of amenities like air conditioning and laundries, as well as some offering weekly or monthly discounted prices, you're sure to find a terrific place to call your home away from home in Uptown.