Photo by Dereem Solomon

St. Augustine Holiday Rentals

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Holiday Rentals in St. Augustine

Dining
2 Bed parking gated modern
2.0 star property
2 Bed parking gated modern
Property grounds
A unique contemporary cabin in the hills of Paramin Trinidad
9.8 out of 10, Exceptional, (6)
"We have visited 15 Caribbean Islands and Trinidad ranks high on the list, and no doubt Bridge Cabin played a major role. Nothing like being awakened by the sounds of Parrots and Toucans in the treetops around you. Absolutely would stay here again. Once you get used to navigating the roads necessary to reach the cabin, you will absolutely be in love! (Also of note, be sure to come in from the North Coast Rd side, not up Paramin Hill!!! )"
A unique contemporary cabin in the hills of Paramin Trinidad
Private kitchen
Very safe 2 bedroom apartment at Piarco Airport Trinidad and Tobago Top security
9.6 out of 10, Exceptional, (4)
"Price value met. Comfortable and Stylish. I just didn't want to leave. Booking another trip."
The price is NZ$261
includes taxes & fees
20 May - 21 May
Very safe 2 bedroom apartment at Piarco Airport Trinidad and Tobago Top security
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Interior
FLVS villas
FLVS villas
Fridge, microwave, oven, stovetop
"Modern Comfort Near Airport & Shopping - The Cozy Condo"
The price is NZ$264
includes taxes & fees
22 May - 23 May
"Modern Comfort Near Airport & Shopping - The Cozy Condo"
Fridge, microwave, oven, stovetop
VACATION APT IN AROUCA, TRINIDAD. 2 BEDROOMS
10.0 out of 10, Exceptional, (1)
"Comfortable, clean and cozy apartment with excellent amenities. Definitely recommended. Excellent host."
The price is NZ$287
includes taxes & fees
24 May - 25 May
VACATION APT IN AROUCA, TRINIDAD. 2 BEDROOMS
Microwave, cookware/dishes/utensils
Beautiful Paradise Hill Villa near Beach
5.0 out of 10, (2)
"Our theme song…When last u been to TnT and yu room not ready Oh Ohhh …. Long Time… No toilet at night (no water)…. The WiFi did come before we when to sleep that night. BUT the people are good hearted people and tried to make the best of the stay. BIG Tanks to the back up maid for coming out and setting us up the best she could."
Beautiful Paradise Hill Villa near Beach
Pool
Pool and Jacuzzi Vacation Home
10.0 out of 10, Exceptional, (5)
"We rented this property while visiting family in POS. Property was really nice in quiet and safe neighbourhood with lovely neighbours, the pool and jacuzzi it’s a great bonus and most of all the communication with Ejay who looked after us was excellent. I can’t recommend enough! "
Pool and Jacuzzi Vacation Home
House (Glencoe Townhome with Loft Jacuzzi an) | Exterior
Glencoe Townhome With Loft Jacuzzi and Pool
3.5 star property
Glencoe Townhome With Loft Jacuzzi and Pool
Fridge, microwave, oven, stovetop
Polaris Courts...Cozy 2 bedroom apt, 2 min from airport
9.8 out of 10, Exceptional, (13)
"What I like most about the property is that it was safe, clean, beautiful and quiet I enjoyed my visit at this property and I’m happy to share my experience with others and can’t wait to return again. "
The price is NZ$261
includes taxes & fees
20 May - 21 May
Polaris Courts...Cozy 2 bedroom apt, 2 min from airport
Exterior
Delightful Log Cabin with plunge pool close to amazing waterfall
10.0 out of 10, Exceptional, (2)
"Jervais was easy to communicate, and the property was amazing. The pictures are very accurate of the cabin, and the surrounding area. Jervais definitely maintains the property well, and made our stay magnificent."
Delightful Log Cabin with plunge pool close to amazing waterfall
Pool
Vista Stays...Garden View
10.0 out of 10, Exceptional, (1)
"Owner was professional, available and knowledgeable. Accommodation was excellent. I was very comfortable and safe. Would definitely recommend to others. Tranquility."
Vista Stays...Garden View
Interior
charming hill top retreat in San Juan Trinidad and Tobago
10.0 out of 10, Exceptional, (1)
"The property was great! It was clean and modern and had onsite laundry which was a plus! The host was easy to reach and they provided all the items you would need for your stay. Would definitely book again!"
The price is NZ$458
includes taxes & fees
24 May - 25 May
charming hill top retreat in San Juan Trinidad and Tobago
Exterior
BEAUTIFUL HOME IN PORT OF SPAIN TRINIDAD
10.0 out of 10, Exceptional, (1)
"Wow. I don’t where to start. Ms.Glenda was absolutely amazing. The meals were all top notch and we didn’t have to want for anything. If there was anything we needed, she made sure to get it for us. Sometimes you see places online and get a different story once you arrives, but this was not the case at all. The rooms were all immaculate and super spacious. And it was nice to relax by the pool after a hard day of fete. We felt safe at all times and worried about nothing. We came as strangers...
BEAUTIFUL HOME IN PORT OF SPAIN TRINIDAD
Pool
Pool +Jacuzzi Gulfview Townhome
Pool +Jacuzzi Gulfview Townhome
Pool
Vista Stsys...Bamboo View
10.0 out of 10, Exceptional, (2)
"This experience was just amazing. The property itself was so serene and beautiful...the lush greenery, the relaxing salt water pool and jacuzzi, simply amazing. We had such a relaxing experience and the property owner Anthony and his wife were so accommodating and friendly, we felt as if we were at home; didn't want to leave, lol. And let's not forget the breakfast, tailored specifically to our palate and sooo tasty. All in all an unforgettable experience and will recommend this stay 100%. We...
Vista Stsys...Bamboo View
Property grounds
Relaxing, private, family friendly, 3 bedroom home
9.0 out of 10, Wonderful, (10)
"Our host was most welcoming, understanding and accommodating. Place was clean, breezy and relaxing. A perfect staycation. 10/10 would recommend"
Relaxing, private, family friendly, 3 bedroom home
Fridge, microwave, oven, stovetop
The "Dous" Modern Apartment
6.0 out of 10, (1)
"I booked this home, after payment i was then alerted by owner that the accommodation isn't available due to renovations. He mentioned having another with no additional cost. I saw some pictures and decided to stay at the new place. However i inquire about the wash and dryer as it was one of the amenities and was assured that the apartment had these items. I arrived at Trinidad and noticed that the location still wasn't sent. I called all day and no response from owner. He finally rang after...
The price is NZ$225
includes taxes & fees
23 May - 24 May
The "Dous" Modern Apartment
Apartment, 1 Bedroom | Private kitchen
Sunflower Apartments Trinidad
3.0 star property
8.8 out of 10, Excellent, (11)
"I come here once a year I like the privacy and secure feeling I will continue to come here as long as it is available "
The price is NZ$173
includes taxes & fees
19 May - 20 May
Sunflower Apartments Trinidad
Private kitchen
A beautiful and safe 3 bedroom home in a gated community
9.8 out of 10, Exceptional, (14)
"My whole family stayed at this lovely three bedroom home. It was quite comfortable and spacious. We really enjoyed ourselves. Can’t wait to do it again at the same location felt safe and everything was right outside and within walking distance security even took the time to help us out get something to eat one night, wonderful wonderful experience"
A beautiful and safe 3 bedroom home in a gated community
Don't see what you're looking for?
See all available properties in St. Augustine
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

Other types of properties in St. Augustine you may be interested in

Dining
Pax Guest House
3.0 star property
9.2 out of 10, Wonderful, (29)
"Beautiful place, very friendly and helpful people, wonderful terrace with masses of hummingbirds, fantastic view from the shared bathroom rooms on the first floor"
The price is NZ$194
includes taxes & fees
26 May - 27 May
Pax Guest House
Dining
2 Bed parking gated modern
2.0 star property
2 Bed parking gated modern
Lobby
Hyatt Regency Trinidad
4.5 star property
9.2 out of 10, Wonderful, (1005)
"Great infinity pool on forth floor over looking the sea. "
The price is NZ$391
includes taxes & fees
21 May - 22 May
Hyatt Regency Trinidad
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

You always said you would go on a dream holiday someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannonball into the deep end. Go ahead, unplug and unwind in style. When you book one of our St. Augustine holiday rentals, the ordinary is in the rearview. Instead of sharing your vacation with hundreds of hotel guests, you get to take advantage of all the space at your private apartment. You also get to enjoy all the amenities of a private residence for a truly unique and memorable stay. Why don’t you take off your shoes and settle in for a while? Your holiday just got upgraded.

As much as you love your vacation rental, it’s always good to get out and explore to soak up St. Augustine. Live like a local: Eat regional food, cheer on the home team, and visit the best cultural attractions in town. No matter the season, there is always something going on in St. Augustine. Seeing all the best attractions is bound to make you fall in love with St. Augustine. Who knows, you may even be tempted to extend your stay. There’s a reason home rentals are so popular here—after a long day of exploration, going back to your very own living room to stretch out is a dream come true. 

It’s your escape so why share it? You deserve your own slice of paradise. Booking your holiday rental on Expedia is simple and safe. Just pick your dates to search for the perfect property and book securely. We let you contact the property owner directly to make any special arrangements. All that’s left to do is show up with bells on and have a memorable vacation. With all the amenities available in St. Augustine short-term rentals, that won’t be hard to do.

Frequently asked questions

Can I find holiday rentals in St. Augustine?

Yes, there are holiday rentals close to the most popular sights in St. Augustine, or you can select a more secluded option if you're looking for a relaxing stay. St. Augustine is known for its football games and university setting. Make sure you have time to check out the restaurants while you're in the area.

What are some of the best holiday rentals that St. Augustine has to offer?

Pool +Jacuzzi Gulfview Townhome: This holiday home rental outside of St. Augustine offers a garden, a BBQ and air conditioning to help you feel perfectly comfortable in your new surroundings. It has 3 bedrooms, as well as a kitchen with a fridge, a microwave and kitchenware, so that you can cook with friends or family.

What can I see and do in St. Augustine?

While exploring the area, visit family-friendly sights like Yerette - Home of the Hummingbird, or get outside and enjoy nature at Queen's Park Savanah. University of the West Indies and Mount St. Benedict Monastery are a couple of places you'll find in the wider area.

What are holiday rentals like in St. Augustine?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in St. Augustine. Holiday rentals offer extras such as kitchens and laundry facilities so you'll feel just like you're staying in your own home. If you're concerned about cleanliness, a holiday rental can offer a sense of security away from public hotel lifts and busy concierge desks while still allowing you the excitement and enjoyment of travel. You'll also get more space in a holiday rental than in a standard hotel, which is another reason why a holiday rental is a great option for small groups.

Recent reviews of St. Augustine properties
Expedia verified reviews