Photo by Dee Val

Uptown holiday rentals

We found 461 holiday rentals — enter your dates for availability
Discover a selection of 121 homes, 44 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:8 Jan - 15 Jan

Interior
Terrace/patio
Private kitchen
Private kitchen
Exceptional
(26 reviews)

Spacious house in lovely St. Augustine Historic District w/ parking

St. Augustine

8% off
S$4,993
for 7 nights, 1 home
S$713 per night
includes taxes & fees
Spacious house in lovely St. Augustine Historic District w/ parking
Room
Property grounds
Interior
Interior
Exceptional
(90 reviews)

The ArtHouse One-of-a-Kind 3BR/2BA Stay Filled with Local Art

St. Augustine

8% off
S$2,842
for 7 nights, 1 home
S$406 per night
includes taxes & fees
The ArtHouse One-of-a-Kind 3BR/2BA Stay Filled with Local Art
Front bedroom with queen bed, fan, highboy, cedar lined closet, chair & bench
Sunroom with comfortable seating for four with blinds for sun glare & privacy
Beautiful sunroom facing San Marco Avenue
Back bedroom closet with cozy robes, extra linens, blanket, and iron
Exceptional
(48 reviews)

Luxurious and Relaxing Elegance Upstairs 🚭

St. Augustine

8% off
S$2,198
for 7 nights, 1 apartment
S$314 per night
includes taxes & fees
Luxurious and Relaxing Elegance Upstairs 🚭
Private kitchen
Interior
Interior
Interior
Exceptional
(7 reviews)

SaraCasa - First Floor House 2Br/1.5Bath

St. Augustine

5% off
S$1,860
for 7 nights, 1 home
S$266 per night
includes taxes & fees
SaraCasa - First Floor House 2Br/1.5Bath
Casa de Florade Flora showing front patio and adirondak chairs
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
S$1,995
for 7 nights, 1 apartment
S$285 per night
includes taxes & fees
132A Relaxed Luxury at Casa de Flora in St Augustine
Interior
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
S$5,123
for 7 nights, 1 home
S$732 per night
includes taxes & fees
Historic Full House 2min walk to Historic Downtown with 75" 8K TV & Gas Grill
Room
Private kitchen
Bathroom
Private kitchen
Exceptional
(56 reviews)

Oasis, 1-bedroom Apt. walk to all of downtown St. Augustine with WiFi, AC

St. Augustine

8% off
S$1,334
for 7 nights, 1 apartment
S$191 per night
includes taxes & fees
Oasis, 1-bedroom Apt. walk to all of downtown St. Augustine with WiFi, AC
Fully renovated kitchen.
Walking into the primary bedroom. There is sooo much natural light. This is one of my favorite rooms.
This is the entrance to the house. It is on the side of the house. In front of where you park.
You will enter through the kitchen.
Exceptional
(7 reviews)

Apothecary - Upper Unit Downtown 2BR

St. Augustine

5% off
S$1,832
for 7 nights, 1 apartment
S$262 per night
includes taxes & fees
Apothecary - Upper Unit Downtown 2BR

  • 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.

More holiday ideas