Uptown holiday lettings
We found 455 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
Exceptional
(116 reviews)
Perfect wedding/beach/golf retreat
St. Augustine
£3,061
for 7 nights, 1 home
£437 per night
includes taxes & fees
Exceptional
(18 reviews)
Charming Home and Cottage in Downtown St Augustine for 14
St. Augustine
£5,635
for 7 nights, 1 home
£805 per night
includes taxes & fees
Exceptional
(48 reviews)
Historic Full House 2min walk to Historic Downtown with 75" 8K TV & Gas Grill
St. Augustine
£3,040
for 7 nights, 1 home
£434 per night
includes taxes & fees
Exceptional
(157 reviews)
Relaxed Elegance at Casa de Flora II in historic St Augustine, Florida 🚭
St. Augustine
£1,429
for 7 nights, 1 home
£204 per night
includes taxes & fees
Exceptional
(12 reviews)
Chic+Eco Friendly! Chefs Kitchen•Quick Walk to Old City and Public Park!
St. Augustine
£5,005
for 7 nights, 1 home
£715 per night
includes taxes & fees
Exceptional
(239 reviews)
C2 Perfect location in historic city center, near beaches, patio, free parking!
St. Augustine
£1,178
for 7 nights, 1 apartment
£168 per night
includes taxes & fees
Exceptional
(48 reviews)
Luxurious and Relaxing Elegance Upstairs 🚭
St. Augustine
£1,537
for 7 nights, 1 apartment
£220 per night
includes taxes & fees
Exceptional
(27 reviews)
132A Relaxed Luxury at Casa de Flora in St Augustine
St. Augustine
£1,261
for 7 nights, 1 apartment
£180 per night
includes taxes & fees
Find spaces that suit your style
House
Condo/Apartment
Cabin
Cottage
Villa
Chalet
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
Casa Maria 3- Historic Apt- Walk to Historic Dist!
Sleeps 6 · 3 bedrooms · 2 bathrooms
Top rated rentals - Uptown
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 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.