Best Vacation Homes in Old Town
House
10.0(1 Review)
2 Bedrooms
1 Bath
8 Guests
Oceanfront
Fireplace/Heating
Pool
Ocean View
R6,525/Night
7 Nights - R45,670
House
10.0(10 Reviews)
4 Bedrooms
3 Baths
8 Guests
2002.09 ft²
- Fireplace/Heating
View
Parking
Air Conditioner
R15,026/Night
7 Nights - R105,180
House
8.0(179 Reviews)
1 Bedroom
1 Bath
- Fireplace/Heating
Kitchen- Parking
- Air Conditioner
R2,325/Night
7 Nights - R16,280
New
House
10.0(1 Review)
3 Bedrooms
2 Baths
8 Guests
- Fireplace/Heating
Balcony/Terrace- Kitchen
- Parking
R2,978/Night
7 Nights - R20,839
House
10.0(10 Reviews)
3 Bedrooms
2 Baths
8 Guests
1097.92 ft²
- Fireplace/Heating
- Parking
- Air Conditioner
Internet
R2,328/Night
7 Nights - R16,296
New
House
9.8(15 Reviews)
3 Bedrooms
2 Baths
8 Guests
1500 ft²
Private Pool- Fireplace/Heating
- Pool
- Ocean View
R4,505/Night
7 Nights - R31,541
New
House
4 Bedrooms
2 Baths
8 Guests
- Fireplace/Heating
Pet Friendly- Air Conditioner
- Internet
R6,579/Night
7 Nights - R46,058
New
House
6 Bedrooms
4 Baths
20 Guests
2400 ft²
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
- Parking
R6,301/Night
7 Nights - R44,102
Old Town Luxury Rentals
House
6 Bedrooms
6 Baths
28 Guests
10763.91 ft²
- Oceanfront
Hot Tub
Spa- Fireplace/Heating
R67,668/Night
7 Nights - R473,680
House
10.0(13 Reviews)
10 Bedrooms
9 Baths
20 Guests
- Private Pool
- Fireplace/Heating
- Pool
- Ocean View
R63,591/Night
7 Nights - R445,130
New
Hotel
8 Baths
3600 ft²
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
- Parking
R52,743/Night
7 Nights - R369,195
House
10.0(2 Reviews)
1 Bedroom
1 Bath
4 Guests
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
- Parking
R35,312/Night
7 Nights - R247,186
House
10.0(23 Reviews)
3 Bedrooms
3 Baths
6 Guests
3000 ft²
- Private Pool
- Oceanfront
- Hot Tub
- Fireplace/Heating
R32,145/Night
7 Nights - R225,022
Villa
10.0(15 Reviews)
5 Bedrooms
4 Baths
12 Guests
4800 ft²
- Private Pool
- Fireplace/Heating
- Pool
- Ocean View
R31,669/Night
7 Nights - R221,692
House
10.0(11 Reviews)
6 Bedrooms
6 Baths
14 Guests
6000 ft²
- Oceanfront
- Hot Tub
- Fireplace/Heating
- Pool
R30,231/Night
7 Nights - R211,620
House
10.0(62 Reviews)
8 Bedrooms
4 Baths
20 Guests
6395 ft²
- Oceanfront
- Fireplace/Heating
- Ocean View
- Balcony/Terrace
R29,081/Night
7 Nights - R203,569
Old Town Pet Friendly Vacation Rentals
House
2 Bedrooms
1 Bath
5 Guests
- Fireplace/Heating
- Pet Friendly
- Air Conditioner
- Internet
R3,821/Night
7 Nights - R26,739
Apartment
10.0(7 Reviews)
1 Bedroom
1 Bath
4 Guests
505.9 ft²
- Fireplace/Heating
- Pet Friendly
- Parking
- Air Conditioner
R3,282/Night
7 Nights - R22,973
Apartment
9.6(42 Reviews)
1 Bedroom
1 Bath
2 Guests
310 ft²
- Oceanfront
- Ocean View
- Balcony/Terrace
- View
R2,744/Night
7 Nights - R19,206
New
House
3 Bedrooms
1 Bath
8 Guests
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
- Kitchen
R3,334/Night
7 Nights - R23,344
Apartment
10.0(6 Reviews)
1 Bedroom
1 Bath
2 Guests
452.08 ft²
- Oceanfront
- Spa
- Fireplace/Heating
- Ocean View
R3,169/Night
7 Nights - R22,181
Cottage
10.0(183 Reviews)
2 Bedrooms
2 Baths
6 Guests
1545 ft²
- Oceanfront
- Fireplace/Heating
- Ocean View
- Balcony/Terrace
R7,085/Night
7 Nights - R49,599
Cottage
10.0(127 Reviews)
1 Bedroom
1 Bath
2 Guests
- Fireplace/Heating
- Pet Friendly
- Kitchen
- Parking
R4,579/Night
7 Nights - R32,058
House
10.0(121 Reviews)
1 Bedroom
1 Bath
2 Guests
503 ft²
- Oceanfront
- Fireplace/Heating
- Ocean View
- Balcony/Terrace
R2,411/Night
7 Nights - R16,878
Old Town Large Vacation Homes
House
10.0(5 Reviews)
2 Bedrooms
3 Baths
10 Guests
1780 ft²
- Oceanfront
- Fireplace/Heating
- Ocean View
- Balcony/Terrace
R4,776/Night
7 Nights - R33,432
House
10.0(8 Reviews)
4 Bedrooms
4 Baths
10 Guests
1603.82 ft²
- Fireplace/Heating
- Parking
- Air Conditioner
- Internet
R10,880/Night
7 Nights - R76,161
House
10.0(167 Reviews)
3 Bedrooms
4 Baths
10 Guests
2200 ft²
- Oceanfront
- Fireplace/Heating
- Ocean View
- Balcony/Terrace
R11,735/Night
7 Nights - R82,142
Villa
8.8(3 Reviews)
1 Bedroom
1 Bath
3 Guests
- Oceanfront
- Fireplace/Heating
- Pool
- Ocean View
R6,005/Night
7 Nights - R42,033
House
10.0(3 Reviews)
7 Bedrooms
7 Baths
14 Guests
2809.38 ft²
- Fireplace/Heating
- View
- Parking
- Air Conditioner
R13,650/Night
7 Nights - R95,544
House
10.0(179 Reviews)
3 Bedrooms
4 Baths
10 Guests
2200 ft²
- Oceanfront
- Fireplace/Heating
- Ocean View
- Balcony/Terrace
R9,472/Night
7 Nights - R66,299
House
10.0(129 Reviews)
5 Bedrooms
3 Baths
11 Guests
2800 ft²
- Private Pool
- Oceanfront
- Fireplace/Heating
- Pool
R17,792/Night
7 Nights - R124,547
House
10.0(83 Reviews)
4 Bedrooms
2 Baths
10 Guests
2200 ft²
- Private Pool
- Oceanfront
- Hot Tub
- Fireplace/Heating
R7,000/Night
7 Nights - R49,001
Why Choose Rent By Owner for your Old Town Vacation Rental Homes?
What makes our Vacation Rentals special?
Verified Listings
Book with confidence knowing every property meets our quality and safety standards.
Unbeatable Value
Enjoy competitive pricing with no hidden fees, providing exceptional value for every stay.
Diverse Options
From cozy cabins to luxurious villas, find a rental that suits your style and needs.
Popular Areas for Old Town Vacation Rentals
Where are the best neighborhoods to stay in Old Town?
When exploring Old Town in St. Augustine, Florida, choosing the right neighborhood to stay in can enhance your entire vacation experience. The area offers a variety of charming neighborhoods, each with its own unique character and convenient access to historic sites, local dining, and vibrant shops. Whether you prefer staying close to the bustling heart of the city or in a quieter, more residential setting, you'll find a range of options that suit your needs. By selecting a well-situated neighborhood in Old Town, you ensure a seamless and enjoyable stay while discovering the rich history and inviting atmosphere of this captivating destination.
St. Augustine Historic District
In this historic area, you will find charming streets and well-preserved architecture that highlight the rich cultural heritage of the region, making it an ideal choice for an authentic stay in Old Town.
View 1346+ Rentals in St. Augustine Historic DistrictDowntown Historic District
This vibrant neighborhood offers easy access to local shops, dining, and entertainment within walking distance, providing a lively atmosphere for your stay near the heart of the region.
View 1776+ Rentals in Downtown Historic DistrictLincolnville
Known for its historic significance and welcoming community, Lincolnville offers a peaceful retreat with unique cultural experiences just moments from the main attractions of Old Town.
View 430+ Rentals in LincolnvilleBest Times to Visit Old Town
When should you plan your Vacation Rentals stay?
Choosing the right time to visit here can enhance your experience, as the area's weather and local events vary throughout the year, making it ideal to plan your stay during the season that best aligns with your vacation preferences.
Peak Season Highlights
Spring (March to May)
During the spring months, you’ll experience pleasant weather that enhances your exploration of this historic area. It’s a popular time for visitors seeking to enjoy outdoor activities and local festivals.
Average Temperature Daytime: 75°F - Nighttime: 55°F
Fall (September to November)
Fall offers mild temperatures and fewer crowds, making it an ideal period for leisurely sightseeing and enjoying the region’s charming atmosphere without peak season congestion.
Average Temperature Daytime: 78°F - Nighttime: 60°F
Off-Season Highlights
Summer (June to August)
In the summer, the area can become quite hot and busy, but it’s a chance to explore with more availability and potentially lower rates on vacation rentals.
Average Temperature Daytime: 88°F - Nighttime: 72°F
Winter (December to February)
Winters are cooler here, with milder weather than many northern destinations, offering a quieter experience for those who prefer avoiding large crowds.
Average Temperature Daytime: 62°F - Nighttime: 45°F
Weekly Weather Forecast for Old Town
How to Book Your Old Town Vacation Rental Home
What's our booking process?
Our platform allows you to browse a curated selection of vacation rentals. Once you find the ideal property, you’ll be redirected to a trusted booking partner to complete your reservation securely.
Booking Steps
01
Search Properties
Use our filters to find the right property that fits your needs.
02
Select a Rental
Click on your preferred listing to view details, amenities, and pricing.
03
Book Online
Follow the link to finalize your reservation directly on the partner’s website.
Explore and book the perfect rental in Old Town
Common Vacation Rentals Amenities
What amenities can you expect?
Our Vacation Rentals are designed to offer all the comforts of home, often with added perks to make your stay unforgettable. Here’s some common amenities to look forward to:
Indoor Features
- Fully-equipped kitchens with modern appliances
- Comfortable living areas with flat-screen TVs
- Free Wi-Fi for staying connected
- Air conditioning and heating for year-round comfort
- In-unit washers and dryers for convenience
- Luxurious bedrooms with premium bedding
- Spa-like bathrooms with soaking tubs or walk-in showers
Outdoor Amenities
- Enjoy a private outdoor patio or balcony for relaxing and dining al fresco.
- Take advantage of landscaped gardens or courtyards that add to the area's charm.
- Make use of an outdoor grilling area to prepare meals while enjoying the regional climate.
- Relax by a shared swimming pool with views of the historic surroundings.
- Benefit from available outdoor seating areas designed for socializing or unwinding.
- Utilize bike or golf cart rentals to explore scenic spots around the region easily.
- Access nearby walking trails or waterfront spaces perfect for outdoor recreation.
Top Attractions Around Old Town
What attractions are nearby?
Enjoy a variety of nearby activities in this charming destination, where you can explore historic sites, browse local shops, and indulge in delicious cuisine all within easy reach from your vacation rental.
Family Activities
- Historic Sightseeing Tours: Explore the charming streets and learn about the area's rich history through engaging guided tours tailored for families visiting here.
- Castillo de San Marcos National Monument: Discover this iconic fortress where your family can immerse themselves in centuries of local history and enjoy stunning views of the region's waterfront.
- St. Augustine Pirate & Treasure Museum: Enter a world of adventure with interactive exhibits and engaging displays that captivate young explorers in the heart of the city.
- Old Town Trolley Tour: Hop on and off at various points around the area, offering a fun and informative way to see the city's highlights suitable for all ages.
Adult Activities
- Historic Walking Tours: Explore the charming streets and learn about the area's rich history through guided or self-guided walking tours that highlight its colonial past and architectural beauty.
- Canoeing and Kayaking: Experience the tranquility of nearby waterways with paddle sports, offering a unique perspective of the region’s natural scenery and waterways.
- Shopping in Boutique Stores: Discover a variety of boutique shops and art galleries filled with local crafts and souvenirs, perfect for finding a special keepsake from your stay.
- Dining at Local Eateries: Enjoy diverse culinary options in cozy taverns and fine restaurants that showcase regional flavors and fresh seafood, enhancing your visit to this historic destination.
Other Places to Stay in Old Town, FL
Spanish Military Hospital Museum
The Oldest Store Museum
Amiro Art and Found
Florida Lost Tribes Museum
Segui-Kirby Smith House
St. Augustine Municipal Marina
Bayfront Carpet Golf
Ximenez-Fatio House Museum
Aviles Street
Moultrie Creek Studios
Father O'Reilly House Museum
Old Town Travel Tips
How Can You Make the Most of Your Stay?
- Explore Local Landmarks: Take time to visit the iconic sites within walking distance to fully immerse yourself in the historic charm of this destination.
- Plan Your Activities Early: Booking tours and experiences ahead of time ensures you make the most of your stay in this area's vibrant cultural scene.
- Choose a Prime Location: Opt for accommodations close to main attractions to maximize your sightseeing and reduce travel time in the region.
- Enjoy the Neighborhood Vibe: Spend leisurely mornings and evenings exploring nearby cafes and shops to get an authentic feel for the area’s atmosphere.
Transportation Options
- Walking: Exploring on foot is a popular way to experience the charming streets and historic sites of this destination's Old Town area.
- Bike Rentals: Renting a bike allows you to leisurely discover the region’s scenic views and historic landmarks at your own pace.
- Street Trolley Tours: Hop-on, hop-off trolley services provide convenient transportation around the area's top attractions with guided commentary.
- Public Transportation: Local bus services offer affordable and reliable options for navigating around the historic district and nearby neighborhoods.
Local Customs Options
- Gullah Heritage:** You’ll notice the Gullah traditions are celebrated here, reflecting a rich African-American cultural influence that’s unique to this area.
- Historic Dress Customs:** Visitors often observe locals dressing in vintage-inspired attire during special events, honoring the region’s colonial history.
- Pirate Spirit:** Embracing its maritime past, the community enjoys themed festivals and reenactments that pay homage to the area’s legendary pirate legends.
- Church Traditions:** The area's religious customs remain vibrant, with many historic churches hosting traditional services and community gatherings throughout the year.
Frequently Asked Questions About Old Town?
1. What are the top vacation rentals in Old Town?
There are a lot of options in Old Town. If you plan on staying in the Old Town area, consider making a reservation for a few nights at one of these properties as these have been rated the Top Vacation Rentals in Old Town:
- MARINA SUNSETS - SAINT AUGUSTINE DOWNTOWN HISTORIC DISTRICT
- A WOW! Pristine, private oceanfront. Luxury 7 unit boutique bldg. St Aug close
- C1, Perfect location in city center with balcony, near beaches, free parking!
- Oceanfront Luxury Next To St Augustine Center - Quiet Vilano Beach, Dogs Welcome
- Walk to EVERYTHING Downtown within minutes. Shotgun House in Lincolnville.
- Ocean Front Condo W/private Beach Access & Minutes From Downtown St. Augustine
- Boathouse Cottage, Historic District, Private Pier, 1 Block to Trolley & Fort
- Center of Historic City- Balcony Overlooks Shops, Restaurants, Bars, Free Parking, Walk Everywhere!
- 💲Historic Lady💲2 Block Stroll to DT- 3Mi to Beach - Optional Guesthouse
- C8, Perfect location, historic downtown, balcony, near beaches, FREE parking!
2. How many vacation rentals have private pools in Old Town?
There are 204 vacation rentals with private pools near Old Town. Top-rated RBO homes that have access to a swimming pool include:
3. Which vacation homes in Old Town are best for families?
If you are looking for a family-friendly vacation home in Old Town, check out one of the following properties as all are highly-rated places to stay with excellent review for families or groups staying in Old Town:
4. How many Rentbyowner vacation rentals are available in Old Town?
Currently, the total number of properties listed by Rent By Owner in 2026 is over 2888 in the Old Town area, and still counting. By aggregating listings from multiple websites, Rent By Owner offers an immense amount of choice of the best RBO properties in Old Town.
5. What is the cancellation policy for vacation rentals in Old Town, St. Augustine?
Cancellation policies vary by listing. You should review the specific property's cancellation terms on the listing page or contact the property owner directly to understand the conditions and potential fees associated with canceling your reservation.
6. How do I find available vacation rentals during my preferred travel dates in Old Town?
Availability depends on the listing and the dates you select. Use the search filters on the booking website to view current options for your desired travel period, and read the property details to ensure it meets your needs before confirming your reservation.
7. Are there any hidden fees or additional charges when booking a vacation rental in this area?
Additional fees such as cleaning, service charges, or taxes may apply depending on the listing. It’s recommended to review the fee breakdown on the property detail page or ask the owner for clarification before finalizing your booking.
8. What amenities are typically included in vacation rentals here?
Most properties in this destination offer amenities like Wi-Fi, kitchen facilities, linens, and parking. However, amenities can vary by listing, so be sure to check the property description and inquire with the owner if you have specific requirements.
9. Is there any assistance available if I encounter issues during my stay?
Support options depend on the property and booking platform. Usually, hosts provide contact information for assistance, and customer service is available through the booking site to help resolve any concerns or problems that may arise during your stay.
Old Town Top Rated Vacation Rentals
Condo
10.0(192 Reviews)
2 Bedrooms
2 Baths
4 Guests
1200 ft²
- Private Pool
- Fireplace/Heating
- Pool
- Ocean View
R4,453/Night
7 Nights - R31,169
Apartment
10.0(161 Reviews)
2 Bedrooms
1 Bath
4 Guests
750 ft²
- Oceanfront
- Fireplace/Heating
- Pool
- Ocean View
R3,173/Night
7 Nights - R22,213
House
10.0(141 Reviews)
4 Bedrooms
3 Baths
8 Guests
3700 ft²
- Private Pool
- Hot Tub
- Fireplace/Heating
- Pool
R26,209/Night
7 Nights - R183,458
Condo
10.0(124 Reviews)
2 Bedrooms
2 Baths
7 Guests
1232 ft²
- Oceanfront
- Fireplace/Heating
- Pool
- Ocean View
R4,422/Night
7 Nights - R30,959
Condo
10.0(104 Reviews)
2 Bedrooms
2 Baths
7 Guests
1232 ft²
- Fireplace/Heating
- Pool
- Ocean View
- Balcony/Terrace
R6,889/Night
7 Nights - R48,225
House
10.0(78 Reviews)
2 Bedrooms
2 Baths
4 Guests
1200 ft²
- Oceanfront
- Fireplace/Heating
- Pool
- Ocean View
R4,140/Night
7 Nights - R28,970
House
10.0(77 Reviews)
3 Bedrooms
3 Baths
6 Guests
2500 ft²
- Private Pool
- Hot Tub
- Fireplace/Heating
- Pool
R6,183/Night
7 Nights - R43,278
House
10.0(57 Reviews)
4 Bedrooms
2 Baths
10 Guests
2500 ft²
- Oceanfront
- Fireplace/Heating
- Pool
- Ocean View
R7,149/Night
7 Nights - R50,035
