Top 5 HomeAway & Vrbo Vacation Rentals In St Augustine, Florida - Updated 2023


St Augustine is the oldest continuously occupied European settlement in the United States. While it definitely has become more of a tourist destination in recent years, its main charms still lie in the myriad of authentic museums it has to offer, from the stoic Lightner Museum to the fun and quirky St Augustine Pirate and Treasure Museum, we are sure that any antique camera lover’s roll will be full by the end of their trip.

With this in mind, we’ve selected the five best HomeAway and Vrbo vacation rentals to stay at if you and a small group of friends are history enthusiasts and wish to explore the delights that St. Augustine has to offer:

2. Charming, colourful house downtown (from 102 USD)

Approaching this house, you are greeted with a picture akin to a tropical getaway. Nestled between swaying trees is your vacation rental with a dreamy light turquoise and lemon yellow exterior, matching the sky and its surroundings perfectly. When you enter, the eclectic mix of paintings, colourful furniture, and large windows is a sight for sore eyes. You’ll be glad to know that this beautiful and functional house also comes with a hot tub and is kid friendly. A similar theme runs through to the bedrooms too, also speckled with interesting, vibrant art and a large window. You’ll surely get a restful sleep in this area, and you’re going to need plenty of it since you’ll be out and about the whole day. That’s because this rental resides on Riberio Street, the location of the St Augustine Distillery. The distillery is just walking distance from the Ximinez Fatio Museum as well, so you can be assured that this HomeAway is a great place for a group who wants a day that is jam packed with activity!

Downtown Saint Augustine Historic District - Hot Tub

Area: Lincolnville, Saint Augustine, FL

Price: from 102 USD

Number of Guests: 2

3. Clean, chic beautiful apartment in Lincolnville (from USD 474)

So you like history, culture, and learning about all things old, but you also like a simple, modern, and sophisticated space? We might have found the perfect place for you to stay. This apartment, with its open-concept space and cosy, minimalist furniture, is a great place to chill out, plan your itinerary and read up before you go to learn more about St Augustine. After a long day of touring the surrounding area, lounge around with your friends in this comfortable, uncrowded setting. Chat away into the night about the things you’ve learnt as you watch the gentle, rolling marsh from the patio just outside. Have a restful night in the comfy, clean, and simple beds. Wake up to the sunrise filtering into your apartment through the large window. Set out for another day of adventure and learning around the area. This apartment, located near Lincolnville, is a great place to stay if you want to find out more about the political struggles of black rights activists in America and the area, as many of its residents in the past were politically active about their rights.

One nearby street is even named after Martin Luther King, and the Lincolnville Museum and Cultural Center is a top place for learning more.

Modern, Lofty & One of a Kind in Downtown St. Augustine

Area: Lincolnville, Saint Augustine, FL

Price: from 131 USD

Number of Guests: 4

Waterfront San Sebastián River Loft (Downtown)
Saint Augustine, Florida, United States
Premier Host  Wifi Available
Private vacation home 9 Guests 3 Bedrooms 4 Bathrooms

Top guest reviews
Amenities & Room:
the beds were comfortable and the ac kept us cool
the kitchen was simple and basic but fit our needs perfectly
great speaker system in the living area with a pool table
everything was very clean and well kept
the bath towels provided were plentiful and the place was clean
the host was easily accessible and very helpful
owners are great people very accommodating live local if you need anything they are right on it
as a place to stay the loft is very comfortable and stylish and in a great location
Read more reviews

4. Blue Bell Cottage (from 170 USD)

This vacation rental is endearing in all sorts of ways, but perhaps the first and most striking way is how cute and bright baby blue it is on the outside! It looks like it jumped right out of a 60s home decor magazine and made its place in this decade. It’s no presidential suite, but the style of the place does look like it’s been decorated with love. It’s a funny smattering of colours and clashing textures, but this adds to the charm and really gives you the sense that you are at a home away from home. No homesickness worries! Just comfort and convenience. The kitchen is just as cute as the rest of the house, resembling a set up in a doll’s house even. Fortunately, it is as as functional as it is delightful. Many long-term guests have reported that they don’t need to eat outside because of how convenient the kitchen is. The bedroom is similarly comfortable like the rest of the house, and has a high ceiling for beating the Floridian heat. It’s conveniently attached to the bathroom so you can easily start your day! And a good start to the day is a must in this area, since your days will be long and full of new things. This property is just a stroll away from the historical grandeur of the Castillo De San Marco Fort and the eccentric and exciting Ripley’s Believe it Or Not.

Blue Bell Cottage, 2 Bedroom, Historic St. Augustine, Pet Friendly, Sleeps 4

Area: Saint Augustine, FL

Price: from 170 USD

Number of Guests: 4

5. A unique mint green house within walking distance of everything! (from 149 USD)

This vacation rental is a stunner with its mint-ice-cream-green colour and wonderful location. Comfortable and functional with 6 sleepers, you can be assured that this place is suitable if you’re coming with a larger group or your family. This kitchen, with its spaciousness, appliances, and fresh stock, will ensure that you can serve up piping hot meals for those staying with you at any time. You can focus on touring the area and finding out more about it and not worry about catering and finding places to eat each evening. When your day is done, you can rest and refresh in these cosy, home-like bedrooms. The outstanding factor for this vacation rental is really its location. You can walk to the historic Aviles Street, the Lightner Museum, Flagler College, Castillo de San Marcos, and even the Bayfront.

Picked the perfect place to stay in St. Augustine! House is beautifully decorated and fully equipped and within walking distance of everything. Best part is that the owner is very organized and easily accessible. Thanks, June! Jane F.
So if you really want to stay in the heart of the historic district, look no further!

Enjoy Modern Comforts In The Heart Of Historic Downtown!

Area: Cordova St, across the Congregation of the Sons of Israel, Lincolnville, Saint Augustine, FL

Price: from 149 USD

Number of Guests: 6

6. Charming one-bedroom apartment for couples in historic downtown St. Augustine

Situated in a private and secluded location, just one block from the ocean, this summer homestay is a great option for vacationers in Florida. Whether you’re in for summer or spring break, this 37 sqm (398 sqft) apartment has cable TV, wifi access, air-conditioning, heater, and free parking in the premises for those who went on a road trip to Florida. Guests can take advantage of the kitchen with a microwave and grill, as well as a coffee maker for sunrise watching sessions which is great with a cup of joe at hand before you go on that morning stroll on the beach.


Address: United States of America (see map)

Price: From 20 USD

Accommodates: 2

Bedrooms: 1

Bathrooms: 1

161 reviews  Wifi Available
Apartment 2 Guests 1 Bedroom 1 Bathroom

Accommodates: 2
Minimum Nights: 2
Refund Policy : 100% refund if you cancel at least 14 days before check-in.

Top guest reviews
Amenities & Room:
it has more capacity than needed; the level is on the right-hand side looking from the front Tee bathroom
Clean comfortable Large bathroom and bedroom has fridge
Also in the bedroom were a small refrigerator-freezer and two dressers
Very comfortable bed and spacious bathroom
There are nice-sized side tables on either side of the bed with fashionable two-bulb lights
The place was very clean and quiet
We had plenty of bath towels
Everything was very clean and neat Check in and out
The unit was as pictured
The residence was clean and very appealing
Glad we got to meet Tom also
Host Tom was easy to communicate with Highly recommended
well vast All plumbing worked flawlessly
We only saw him once but knew he was nearby and would be there if we needed anything If we are in the area again
so we could sit outside and enjoy the nice weather Beach
The Reef restaurant is just a bit north of Boat Club Dr
We were very pleased with the location of the residence and the neighborhood Very quiet
About a 5-10 minute drive to downtown St
We arrived 10/4/19 for a wedding the next day at a beach house 10 minutes north
There is no inside "sitting" space
Read more reviews

7. Stunning two-bedroom home for four in Downtown Historic District (from USD 305)

Stay in a stylish garden home for four in one of the most historic parts of Florida. For 382 USD a night, you and your family or friends can experience living in a historic neighborhood and make use of superb facilities like cable TV, wifi access, a stereo, books, and a music library for those who wish to stay entertained indoors. There’s a beautiful garden and balcony for those who like to spend breakfast outdoors early in the morning before heading out to explore the city.

Downtown Garden Home in the Center of the Historic District with Private Parking

Address: 43 ½ Cordova Street (see map)

Price: From 228 USD

Number of Guests: 4

Bedrooms: 2

Bathrooms: 2

Downtown Garden Home in the Center of the Historic District with Private Parking
201 reviews  Wifi Available
House 4 Guests 2 Bedrooms 2 Bathrooms

Accommodates: 4
Minimum Nights: 3
Refund Policy : 100% refund if you cancel at least 60 days before check-in.

Top guest reviews
the property we very clean very comfortable and quiet
inside the house was immaculately clean and had all the creature comforts you could expect
beds very comfortable very clean and well-appointed - great host
the home was beautiful very clean and had everything we needed
the owner made sure all our needs were met
thank you david & libby for being such wonderful hosts
the owners are awesome
the owner is very nice and gave us great dining tips
the home is beautiful and the owners fantastic and attentive to every detail
the location is perfect a 5 minute walk from the heart of downtown st augustine
walk to the best breakfast place in town just two buildings away
this house is in the perfect location for exploring the historic area of st augustine
easy walking to the historic district and the many fine restaurants
perfect weekend getaway you couldn't find a better location able to park the car and leave it
Read more reviews

8. Homey little cottage for four in Old City Augustine near Vilano Beach (from USD 133)

Travelers who like to stay near the beaches when in Florida can experience beach life but also the historic part of Augustine at a local’s homestay. Better than a hotel, this charming cottage can occupy four people and give them access to the entire home with everything they need. Bathroom toiletries are provided, bedsheets are freshly washed, and the kitchen is stocked with updated cookware and appliances. Guests are in close distance to Vilano Beach and Crescent Beach, but there is also the city center where art galleries, museums, restaurants, and shops are often visited by locals and travelers alike.

Little San Filipe Cottage in St. Augustine Walking District- Old City sites steps from front door!

Address: Dummy Full Address (see map)

Price: From 148 USD

Number of Guests: 4

Bedrooms: 1

Bathrooms: 1

Historic Cottage in St. Augustine Walking District- Old City sites steps from front door
197 reviews
House 4 Guests 1 Bedroom 1 Bathroom

Accommodates: 4
Minimum Nights: 3
Refund Policy : 100% refund if you cancel at least 45 days before check-in.

Top guest reviews
Amenities & Room:
the place was appointed well and we loved breakfast in the big open kitchen area
clean comfy bed kitchen & coffee maker
it is very well maintained very clean and had everything we needed for our stay
the home was very clean quaint had everything we needed and was literally a short walk to everything
the owner was next door and he was so helpful m
ric and martha are great host
ron was very accommodating and easy to work with
it was nice to interact with the owner as that is becoming rare in the stvr world
we appreciated the tips our host provided regarding the the local restaurants we would enjoy
this place is in the best location in the city
we truly enjoyed our vacation and this great little location made it all the better
it was great to be able to park the car and walk to everything
we loved the location of the home in particular
perfect location to pristine beaches and flagler college
Read more reviews

St Augustine: a blend of tourist attractions and local flavours

It’s undeniable that St Augustine, and Florida in general, is a place where many come to take refuge from the cold winter in other parts of the U.S. While many popular travel destinations are often rigged with tourist traps and overpriced packages, St Augustine remains deeply rooted and proud of its many historical connections, making the city a sight worth seeing. Choose your perfect HomeAway rental, book your trip, and have a great time in St Augustine!

Disclosure: Trip101 selects the listings in our articles independently. Some of the listings in this article contain affiliate links.

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My name is Kimberlyn, I'm a huge fan of interesting stories and places. I love memorizing wicked facts and quirky histories. I also draw a lot on the side.

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