
Uptown holiday rentals
We found 382 holiday rentals — enter your dates for availability
Discover a selection of 140 homes, 27 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:3 Oct - 10 Oct
Image gallery for Ancient City Cottage

9.89.8 out of 10 rating
Exceptional
(27 reviews)
Ancient City Cottage
St. Augustine, FL
7% off
Price is S$1,582
S$1,582
S$226 per night
includes taxes & fees
Image gallery for Updated Downtown Cottage / Pet Friendly / Sanitized

1010 out of 10 rating
Exceptional
(82 reviews)
Updated Downtown Cottage / Pet Friendly / Sanitized
St. Augustine, FL
7% off
Price is S$2,141
S$2,141
S$306 per night
includes taxes & fees
Image gallery for Villa 1928 “Pumpkin” -Luxe Home- Hidden Gem in the heart of the “Oldest City”

9.49.4 out of 10 rating
Exceptional
(16 reviews)
Villa 1928 “Pumpkin” -Luxe Home- Hidden Gem in the heart of the “Oldest City”
St. Augustine, FL
8% off
Price is S$4,010
S$4,010
S$573 per night
includes taxes & fees
Image gallery for 4BR2BA - Near Historic District

1010 out of 10 rating
Exceptional
(6 reviews)
4BR2BA - Near Historic District
St. Augustine, FL
15% off
Price is S$2,527
S$2,527
S$361 per night
includes taxes & fees
Image gallery for Pet friendly Iconic Magnolia Ave, Fountain of Youth, 4 min to beach & Downtown

1010 out of 10 rating
Exceptional
(5 reviews)
Pet friendly Iconic Magnolia Ave, Fountain of Youth, 4 min to beach & Downtown
St. Augustine, FL
8% off
Price is S$3,444
S$3,444
S$492 per night
includes taxes & fees
Image gallery for Charming 2BR Uptown Cottage - Artsy & Vibrant!

1010 out of 10 rating
Exceptional
(36 reviews)
Charming 2BR Uptown Cottage - Artsy & Vibrant!
St. Augustine, FL
8% off
Price is S$2,721
S$2,721
S$389 per night
includes taxes & fees
Image gallery for Luxe Lemon Loft in Historic Downtown St Aug

1010 out of 10 rating
Exceptional
(38 reviews)
Luxe Lemon Loft in Historic Downtown St Aug
St. Augustine, FL
8% off
Price is S$1,424
S$1,424
S$203 per night
includes taxes & fees
Image gallery for 💲Romantic Renovated Secret Garden💲 Marble Floors & Bath – DT Just Half Mile - Beach Only 3

1010 out of 10 rating
Exceptional
(76 reviews)
💲Romantic Renovated Secret Garden💲 Marble Floors & Bath – DT Just Half Mile - Beach Only 3
St. Augustine, FL
8% off
Price is S$1,973
S$1,973
S$282 per night
includes taxes & fees
Image gallery for Courtyard Flat l City Center l Hot Tub

9.69.6 out of 10 rating
Exceptional
(24 reviews)
Courtyard Flat l City Center l Hot Tub
St. Augustine, Florida
7% off
Price is S$2,222
S$2,222
S$317 per night
includes taxes & fees
Image gallery for Stay in A Castle In St. Augustine, Hot Tub, Fireplace

9.69.6 out of 10 rating
Exceptional
(9 reviews)
Stay in A Castle In St. Augustine, Hot Tub, Fireplace
St. Augustine, Florida
7% off
Price is S$5,475
S$5,475
S$782 per night
includes taxes & fees
Image gallery for 8 Park l Dog Friendly l Outdoor Oasis l Mins to Beach

9.89.8 out of 10 rating
Exceptional
(28 reviews)
8 Park l Dog Friendly l Outdoor Oasis l Mins to Beach
St. Augustine, Florida
7% off
Price is S$2,427
S$2,427
S$347 per night
includes taxes & fees
Image gallery for Comfy Safe Quiet Haven, Dog Friendly! 2 Miles to Downtown or to Vilano Beach

9.89.8 out of 10 rating
Exceptional
(25 reviews)
Comfy Safe Quiet Haven, Dog Friendly! 2 Miles to Downtown or to Vilano Beach
St. Augustine, FL
7% off
Price is S$1,920
S$1,920
S$274 per night
includes taxes & fees
Image gallery for Rooftop View | Near Eats, Waterfront & Attractions

9.69.6 out of 10 rating
Exceptional
(22 reviews)
Rooftop View | Near Eats, Waterfront & Attractions
St. Augustine, Florida
7% off
Price is S$1,876
S$1,876
S$268 per night
includes taxes & fees
Image gallery for Pool + Spa, Downtown, by Beach, FOY, Add Golf Cart

1010 out of 10 rating
Exceptional
(10 reviews)
Pool + Spa, Downtown, by Beach, FOY, Add Golf Cart
St. Augustine, Florida
7% off
Price is S$3,837
S$3,837
S$548 per night
includes taxes & fees
Image gallery for Lofty Treetop Apt. 2bd/1.5ba pet friendly. Close to everything.

1010 out of 10 rating
Exceptional
(23 reviews)
Lofty Treetop Apt. 2bd/1.5ba pet friendly. Close to everything.
St. Augustine, FL
12% off
Price is S$1,431
S$1,431
S$204 per night
includes taxes & fees
Image gallery for Charming 1-bedroom cottage in historic downtown St. Augustine

1010 out of 10 rating
Exceptional
(5 reviews)
Charming 1-bedroom cottage in historic downtown St. Augustine
St. Augustine, FL
8% off
Price is S$1,953
S$1,953
S$279 per night
includes taxes & fees
Image gallery for Courtyard, Walkable Area, Pet-Friendly & Parking

9.69.6 out of 10 rating
Exceptional
(22 reviews)
Courtyard, Walkable Area, Pet-Friendly & Parking
St. Augustine, Florida
6% off
Price is S$1,911
S$1,911
S$273 per night
includes taxes & fees
Image gallery for Family friendly, Gameroom & Outdoor Space Close to Downtown & St Augustine Beach

1010 out of 10 rating
Exceptional
(15 reviews)
Family friendly, Gameroom & Outdoor Space Close to Downtown & St Augustine Beach
St. Augustine, FL
17% off
Price is S$2,044
S$2,044
S$292 per night
includes taxes & fees
Image gallery for Anastasia Viletta - Cozy Style Near Downtown & The Beach

1010 out of 10 rating
Exceptional
(6 reviews)
Anastasia Viletta - Cozy Style Near Downtown & The Beach
St. Augustine, FL
8% off
Price is S$2,104
S$2,104
S$301 per night
includes taxes & fees
Image gallery for Cozy Uptown Guest House

9.69.6 out of 10 rating
Exceptional
(22 reviews)
Cozy Uptown Guest House
St. Augustine, FL
7% off
Price is S$1,151
S$1,151
S$164 per night
includes taxes & fees
Image gallery for Uptown Classic Bungalow Walk to Castillo de San Marcos, Ripley's, Restaurants!!!

1010 out of 10 rating
Exceptional
(19 reviews)
Uptown Classic Bungalow Walk to Castillo de San Marcos, Ripley's, Restaurants!!!
St. Augustine, FL
14% off
Price is S$1,318
S$1,318
S$188 per night
includes taxes & fees
Image gallery for Pet friendly, but please check traveling with pets, with short walk to town.

9.89.8 out of 10 rating
Exceptional
(35 reviews)
Pet friendly, but please check traveling with pets, with short walk to town.
St. Augustine, FL
6% off
Price is S$1,720
S$1,720
S$246 per night
includes taxes & fees
Image gallery for Fullerwood Park Retreat 5 min to Downtown Sleeps 6

9.29.2 out of 10 rating
Wonderful
(15 reviews)
Fullerwood Park Retreat 5 min to Downtown Sleeps 6
St. Augustine, Florida
7% off
Price is S$1,845
S$1,845
S$264 per night
includes taxes & fees
Image gallery for Best Location St Aug, Grand Luxurious Historic, Outdoor kitchen, WetBar, Beach

1010 out of 10 rating
Exceptional
(19 reviews)
Best Location St Aug, Grand Luxurious Historic, Outdoor kitchen, WetBar, Beach
St. Augustine, FL
8% off
Price is S$9,450
S$9,450
S$1,350 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
Map Attractions
Find the best place to stay - Uptown
Cozy In Town Cottage! Walk to Everything! Pet Friendly!
Sleeps 4 · 2 bedrooms · 1 bathroom
9.89.8 out of 10
Exceptionalexceptional
147 reviews(147 reviews)
$300 in Free Tickets Daily! Near Historic Downtown, River, Kayaks Included with Short Walk to Launch
Sleeps 10 · 3 bedrooms · 2 bathrooms
1010 out of 10
Exceptionalexceptional
63 reviews(63 reviews)
Historic Full House 2min walk to Historic Downtown with 75" 8K TV & Gas Grill
Sleeps 8 · 2 bedrooms · 2 bathrooms
9.29.2 out of 10
Wonderfulwonderful
26 reviews(26 reviews)
Charming, historic home with balcony, enclosed yard, A/C - near downtown & beach
Sleeps 6 · 3 bedrooms · 2 bathrooms
8.08.0 out of 10
Very goodvery good
29 reviews(29 reviews)
The Pink Door - Walk to Downtown / Super Clean !
Sleeps 6 · 3 bedrooms · 2 bathrooms
1010 out of 10
Exceptionalexceptional
62 reviews(62 reviews)
Southern Charmer w/ Pool and Stellar Location-Walk to Everything Downtown!
Sleeps 8 · 4 bedrooms · 2+ bathrooms
1010 out of 10
Exceptionalexceptional
58 reviews(58 reviews)
- 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, laundry, 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.