Uptown holiday homes
We found 449 holiday rentals — enter your dates for availability
Discover a selection of 124 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:13 Nov - 20 Nov
Exceptional
(18 reviews)
Magnolia Ave Peacock House Fountain of Youth, 4 min to beach & Downtown
St. Augustine
NZ$4,633
for 7 nights, 1 home
NZ$662 per night
includes taxes & fees
Exceptional
(115 reviews)
Perfect wedding/beach/golf retreat
St. Augustine
NZ$5,553
for 7 nights, 1 home
NZ$793 per night
includes taxes & fees
Exceptional
(8 reviews)
Charming Victorian Home in beautiful St. Augustine with WiFi, AC
St. Augustine
NZ$4,097
for 7 nights, 1 home
NZ$585 per night
includes taxes & fees
Exceptional
(76 reviews)
Luxe Lemon Loft in Historic Downtown St Aug
St. Augustine
NZ$1,908
for 7 nights, 1 home
NZ$273 per night
includes taxes & fees
Exceptional
(63 reviews)
Cozy cottage in a cute neighborhood with parking, close to historic downtown!
St. Augustine
NZ$1,644
for 7 nights, 1 home
NZ$235 per night
includes taxes & fees
Exceptional
(157 reviews)
Relaxed Elegance at Casa de Flora II in historic St Augustine, Florida 🚭
St. Augustine
NZ$2,825
for 7 nights, 1 home
NZ$404 per night
includes taxes & fees
Exceptional
(79 reviews)
💲Romantic Renovated Secret Garden💲 Marble Floors & Bath – DT Just Half Mile - Beach Only 3
St. Augustine
NZ$2,863
for 7 nights, 1 home
NZ$409 per night
includes taxes & fees
Exceptional
(116 reviews)
Three Bedroom, Sanitized, Pet Friendly Bungalow
St. Augustine
NZ$3,128
for 7 nights, 1 home
NZ$447 per night
includes taxes & fees
Wonderful
(85 reviews)
DOWNTOWN COZY APARTMENT
St. Augustine
NZ$1,670
for 7 nights, 1 apartment
NZ$239 per night
includes taxes & fees
Exceptional
(83 reviews)
COMFY DOWNTOWN SPACE
St. Augustine
NZ$1,588
for 7 nights, 1 apartment
NZ$227 per night
includes taxes & fees
Exceptional
(26 reviews)
132A Relaxed Luxury at Casa de Flora in St Augustine
St. Augustine
NZ$2,587
for 7 nights, 1 apartment
NZ$370 per night
includes taxes & fees
Wonderful
(473 reviews)
The Red Cottage ~ 5 min. stroll to Historic St. George Street - on site parking
St. Augustine
NZ$1,861
for 7 nights, 1 cottage
NZ$266 per night
includes taxes & fees
Exceptional
(47 reviews)
Luxurious and Relaxing Elegance Upstairs 🚭
St. Augustine
NZ$2,884
for 7 nights, 1 apartment
NZ$412 per night
includes taxes & fees
Exceptional
(55 reviews)
Oasis, 1-bedroom Apt. walk to all of downtown St. Augustine with WiFi, AC
St. Augustine
NZ$1,591
for 7 nights, 1 apartment
NZ$227 per night
includes taxes & fees
Exceptional
(162 reviews)
Perfect Location! Situated In The Eclectic Uptown Area.
St. Augustine
NZ$1,588
for 7 nights, 1 apartment
NZ$227 per night
includes taxes & fees
Exceptional
(54 reviews)
💲Grand Oak - Renovated 1885 Queen Anne - 1 Block Stroll to Historic DT - Beach only 3 Mi💲
St. Augustine
NZ$2,602
for 7 nights, 1 home
NZ$372 per night
includes taxes & fees
Exceptional
(87 reviews)
The ArtHouse: Where Industrial Charm Meets Creative Inspiration
St. Augustine
NZ$3,794
for 7 nights, 1 home
NZ$542 per night
includes taxes & fees
Exceptional
(239 reviews)
C2 Perfect location in historic city center, near beaches, patio, free parking!
St. Augustine
NZ$2,120
for 7 nights, 1 apartment
NZ$303 per night
includes taxes & fees
Exceptional
(79 reviews)
Old town historic home
St. Augustine
NZ$2,253
for 7 nights, 1 home
NZ$322 per night
includes taxes & fees
Exceptional
(47 reviews)
Adorable Uptown Cottage-Steps to attractions! Perfect for families and couples!
St. Augustine
NZ$3,038
for 7 nights, 1 home
NZ$434 per night
includes taxes & fees
Exceptional
(5 reviews)
Apothecary - Upper Unit Downtown 2BR
St. Augustine
NZ$2,311
for 7 nights, 1 apartment
NZ$330 per night
includes taxes & fees
Find spaces that suit your style
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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
Minutes away from the beach and walking distance into town
Sleeps 5 · 3 bedrooms · 2 bathrooms
Stay Downtown St. Augustine 3BR and Parking
Sleeps 10 · 3 bedrooms · 3 bathrooms
Historic District Dream - 3 BR Beautiful Bungalow! Walk to All Attractions!
Sleeps 5 · 3 bedrooms · 1 bathroom
Historic! Walk to Downtown Attractions and Restaurants! Courtyard, Parking, $300 in Free Tickets!
Sleeps 4 · 2 bedrooms · 1+ bathroom
Charming Victorian Home in beautiful St. Augustine with WiFi, AC
Sleeps 8 · 3 bedrooms · 2 bathrooms
Walker House c1888-Nat'l Reg of Historic Places
Sleeps 6 · 3 bedrooms · 3 bathrooms
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 home 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 Bookabach holiday homes 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 home. Put in your Uptown travel dates to view your available options on Bookabach. 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 home in Uptown?
The minimum age allowed can vary across properties on Bookabach, 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 home in Uptown for?
How long you can book a holiday home 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
- Castle Otttis Holiday Rentals
- Spanish Trace Holiday Rentals
- St. George Street Holiday Rentals
- St. Augustine Lighthouse & Maritime Museum Holiday Rentals
- Ocean Villas Holiday Rentals
- Island South Holiday Rentals
- Ocean Village Club Holiday Rentals
- Seaside Villas Holiday Rentals
- St. Augustine Holiday Rentals
- Island House Holiday Rentals
- St. Augustine Alligator Farm Zoological Park Holiday Rentals
- Captains Quarters Holiday Rentals
- Crescent Beach Holiday Rentals
- St. Augustine Historic District Holiday Rentals
- St. Augustine South Holiday Rentals
- Creston House Holiday Rentals
- Pier Point South Holiday Rentals
- Butler Beach Holiday Rentals
- Tradewinds Holiday Rentals
- Ocean Sunrise Holiday Rentals
- St. Augustine Beach & Tennis Resort Holiday Rentals
- Beacher's Lodge Holiday Rentals
- Vilano Beach Holiday Rentals
- South Ponte Vedra Beach Holiday Rentals
- Sand Dollar Holiday Rentals
- St. Augustine Beach Holiday Rentals
- Seaside at Anastasia Holiday Rentals
- Sea Haven Holiday Rentals
- Sea Winds Holiday Rentals
- St. Johns County Holiday Rentals
- Resorts in St. Augustine
- Beach rentals in St. Augustine
- Resorts in Daytona Beach