Discover Your Perfect Downtown Historic District Vacation Homes

Best Vacation Homes in Downtown Historic District

Apartment
like-icon10.0
Exceptional
(202 Reviews)
1 Bedroom 1 Bath 4 Guests 900 ft²
  • Parking
    Parking
  • Kitchen
    Kitchen
More amenities
R3,963/Night 7 Nights - R27,738
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House
like-icon10.0
Exceptional
(10 Reviews)
4 Bedrooms 3 Baths 8 Guests 2002.09 ft²
  • Parking
    Parking
  • View
    View
More amenities
R15,346/Night 7 Nights - R107,420
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Bed & Breakfast
Map-icon
like-icon10.0
Exceptional
(12 Reviews)
1 Bedroom 1 Bath
  • Parking
    Parking
  • Balcony/Terrace
    Balcony/Terrace
More amenities
R3,592/Night 7 Nights - R25,146
New
House
like-icon10.0
Exceptional
(101 Reviews)
3 Bedrooms 2 Baths 6 Guests 1466 ft²
  • Oceanfront
    Oceanfront
  • Parking
    Parking
More amenities
R8,280/Night 7 Nights - R57,953
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House
Map-icon
like-icon10.0
Exceptional
(10 Reviews)
3 Bedrooms 2 Baths 8 Guests 1097.92 ft²
  • Parking
    Parking
  • Air Conditioner
    Air Conditioner
More amenities
R2,378/Night 7 Nights - R16,643
House
like-icon10.0
Exceptional
(60 Reviews)
3 Bedrooms 2 Baths 6 Guests 1466 ft²
  • Oceanfront
    Oceanfront
  • Parking
    Parking
More amenities
R8,255/Night 7 Nights - R57,788
New
House
Map-icon
like-icon10.0
Exceptional
(50 Reviews)
2 Bedrooms 2 Baths 6 Guests 900 ft²
  • Parking
    Parking
  • Kitchen
    Kitchen
More amenities
R5,805/Night 7 Nights - R40,633
New
House
Map-icon
like-icon10.0
Exceptional
(33 Reviews)
3 Bedrooms 2 Baths 7 Guests 1243 ft²
  • Oceanfront
    Oceanfront
  • Parking
    Parking
More amenities
R7,096/Night 7 Nights - R49,681

Downtown Historic District Luxury Rentals

House
like-icon10.0
Exceptional
(13 Reviews)
10 Bedrooms 9 Baths 20 Guests
  • Private Pool
    Private Pool
  • Parking
    Parking
More amenities
R71,184/Night 7 Nights - R498,284
Hotel
8 Baths 3600 ft²
  • Parking
    Parking
  • Balcony/Terrace
    Balcony/Terrace
More amenities
R43,601/Night 7 Nights - R305,205
House
like-icon10.0
Exceptional
(2 Reviews)
1 Bedroom 1 Bath 4 Guests
  • Parking
    Parking
  • Balcony/Terrace
    Balcony/Terrace
More amenities
R39,080/Night 7 Nights - R273,553
House
Map-icon
4 Bedrooms 2 Baths 8 Guests
  • Air Conditioner
    Air Conditioner
  • Internet
    Internet
More amenities
R37,930/Night 7 Nights - R265,513
House
Map-icon
like-icon10.0
Exceptional
(23 Reviews)
3 Bedrooms 3 Baths 6 Guests 3000 ft²
  • Private Pool
    Private Pool
  • Oceanfront
    Oceanfront
More amenities
R33,590/Night 7 Nights - R235,132
New
House
Map-icon
1 Bedroom 1 Bath 6 Guests
  • Child Friendly
    Child Friendly
  • Security/Safety
    Security/Safety
R30,983/Night 7 Nights - R216,888
Villa
like-icon10.0
Exceptional
(15 Reviews)
5 Bedrooms 4 Baths 12 Guests 4800 ft²
  • Private Pool
    Private Pool
  • Parking
    Parking
More amenities
R30,213/Night 7 Nights - R211,489
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House
Map-icon
5 Bedrooms 6 Baths 14 Guests 3681.26 ft²
  • Parking
    Parking
  • Pool
    Pool
More amenities
R29,642/Night 7 Nights - R207,493

Downtown Historic District Pet Friendly Vacation Rentals

New
House
like-icon10.0
Exceptional
(21 Reviews)
6 Bedrooms 4 Baths 12 Guests 2932 ft²
  • Parking
    Parking
  • Balcony/Terrace
    Balcony/Terrace
More amenities
R19,387/Night 7 Nights - R135,703
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Apartment
Map-icon
like-icon10.0
Exceptional
(7 Reviews)
1 Bedroom 1 Bath 4 Guests 505.9 ft²
  • Parking
    Parking
  • Air Conditioner
    Air Conditioner
More amenities
R3,352/Night 7 Nights - R23,462
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Condo
Map-icon
1 Bedroom 1 Bath
  • Oceanfront
    Oceanfront
  • Hot Tub
    Hot Tub
More amenities
R9,527/Night 7 Nights - R66,688
New
House
Map-icon
like-icon10.0
Exceptional
(20 Reviews)
3 Bedrooms 2 Baths 8 Guests
  • Parking
    Parking
  • Kitchen
    Kitchen
More amenities
R5,733/Night 7 Nights - R40,138
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Apartment
Map-icon
like-icon10.0
Exceptional
(6 Reviews)
1 Bedroom 1 Bath 2 Guests 452.08 ft²
  • Oceanfront
    Oceanfront
  • Parking
    Parking
More amenities
R3,236/Night 7 Nights - R22,653
House
Map-icon
like-icon10.0
Exceptional
(16 Reviews)
4 Bedrooms 2 Baths 8 Guests 2928 ft²
  • Parking
    Parking
  • Balcony/Terrace
    Balcony/Terrace
More amenities
R5,393/Night 7 Nights - R37,744
New
House
like-icon10.0
Exceptional
(13 Reviews)
5 Bedrooms 4 Baths 12 Guests
  • Oceanfront
    Oceanfront
  • Parking
    Parking
More amenities
R16,130/Night 7 Nights - R112,902
New
House
Map-icon
like-icon10.0
Exceptional
(11 Reviews)
2 Bedrooms 2 Baths 8 Guests 1249 ft²
  • Parking
    Parking
  • Balcony/Terrace
    Balcony/Terrace
More amenities
R7,350/Night 7 Nights - R51,448

Downtown Historic District Large Vacation Homes

House
Map-icon
like-icon10.0
Exceptional
(2 Reviews)
4 Bedrooms 4 Baths 12 Guests
  • Hot Tub
    Hot Tub
  • Parking
    Parking
More amenities
R11,194/Night 7 Nights - R78,361
star-icons-4
House
like-icon10.0
Exceptional
(8 Reviews)
4 Bedrooms 4 Baths 10 Guests 1603.82 ft²
  • Parking
    Parking
  • Air Conditioner
    Air Conditioner
More amenities
R11,112/Night 7 Nights - R77,783
House
Map-icon
3 Bedrooms 3 Baths 10 Guests
  • Parking
    Parking
  • Pool
    Pool
More amenities
R5,333/Night 7 Nights - R37,331
New
Villa
Map-icon
1 Bedroom 4 Baths 8 Guests
  • Parking
    Parking
  • Balcony/Terrace
    Balcony/Terrace
More amenities
R19,790/Night 7 Nights - R138,527
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House
Map-icon
like-icon10.0
Exceptional
(3 Reviews)
7 Bedrooms 7 Baths 14 Guests 2809.38 ft²
  • Parking
    Parking
  • View
    View
More amenities
R13,941/Night 7 Nights - R97,580
New
House
Map-icon
6 Bedrooms 4 Baths 13 Guests 2486 ft²
  • Parking
    Parking
  • Ocean View
    Ocean View
More amenities
R15,143/Night 7 Nights - R106,000
New
House
Map-icon
4 Bedrooms 3 Baths 10 Guests 2188 ft²
  • Parking
    Parking
  • Pool
    Pool
More amenities
R6,280/Night 7 Nights - R43,952
House
like-icon10.0
Exceptional
(179 Reviews)
3 Bedrooms 4 Baths 10 Guests 2200 ft²
  • Oceanfront
    Oceanfront
  • Parking
    Parking
More amenities
R16,541/Night 7 Nights - R115,791

Why Choose Rent By Owner for your Downtown Historic District Vacation Rental Homes?

What makes our Vacation Rentals special?

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Verified Listings
Book with confidence knowing every property meets our quality and safety standards.
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Unbeatable Value
Enjoy competitive pricing with no hidden fees, providing exceptional value for every stay.
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Diverse Options
From cozy cabins to luxurious villas, find a rental that suits your style and needs.

Best Times to Visit Downtown Historic District

When should you plan your Vacation Rentals stay?

To make the most of your stay in this charming destination, consider visiting during the shoulder seasons when the weather is pleasant and the area is less crowded, ensuring a more relaxed experience with your chosen vacation rentals.

Peak Season Highlights

spring
Spring (March to May)

During spring, the area dawns with mild temperatures and vibrant local events, making it an ideal time to enjoy the historic charm and cultural festivities.

Average Temperature Daytime: 75°F - Nighttime: 60°F
autumn
Fall (September to November)

Autumn offers pleasant weather and fewer crowds, allowing you to explore the historic district's architecture and landmarks comfortably.

Average Temperature Daytime: 77°F - Nighttime: 62°F

Off-Season Highlights

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Summer (June to August)

Summertime in this destination features higher temperatures and increased humidity, but it's also when local festivals and events are at their peak.

Average Temperature Daytime: 89°F - Nighttime: 75°F
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Winter (December to February)

Winter presents cooler temperatures and a quieter atmosphere, providing a relaxed experience for exploring the historic district at your own pace.

Average Temperature Daytime: 63°F - Nighttime: 48°F

Weekly Weather Forecast for Downtown Historic District

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.

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 courtyard perfect for relaxing after exploring the historic streets.
  • Take advantage of communal gardens or green spaces that provide a peaceful setting in this charming area.
  • Utilize on-site outdoor dining areas to savor meals amidst the scenic surroundings of the region.
  • Make use of designated BBQ or grilling stations to host casual outdoor meals with family or friends.
  • Relax by an outdoor swimming pool or have access to nearby pools within the community or complex.
  • Benefit from well-maintained walking paths or bike trails that help you explore the historic district and beyond.
  • Avail outdoor recreational amenities like tennis courts or fitness areas for an active stay here.
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Family Activities

  • Historic Walking Tour: Discover the area's rich history on a guided walking tour that takes you through centuries-old streets and landmarks, making it a perfect family activity in the region.
  • St. Augustine Pirate & Treasure Museum: Engage your family with interactive exhibits and pirate adventures at this museum, offering an educational and entertaining experience right here in the destination.
  • Visit the oldest masonry fort in the continental United States, where your family can explore historic battlements and enjoy scenic views of the waterfront.
  • Flagler College Campus Tour: Wander through this stunning historic college campus, renowned for its architectural beauty and fascinating history, providing an inspiring outing for all ages.
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Adult Activities

  • Historic Walking Tours: Immerse yourself in the area's rich history by exploring the well-preserved streets and landmarks on guided or self-guided tours.
  • Relaxing River Cruises: Enjoy a peaceful cruise along the scenic waterways that showcase the region's natural beauty and historic sites from a unique perspective.
  • Art Galleries and Studios: Discover local creativity by visiting vibrant art galleries and studios that highlight the region’s cultural heritage and contemporary artistry.
  • Dining Experiences: Savor authentic cuisine at charming eateries and fine dining establishments nestled within the historic district, offering a taste of the area's culinary traditions.

Other Places to Stay in Downtown Historic District, FL

Downtown Historic District Travel Tips

How Can You Make the Most of Your Stay?

  • Explore local attractions early: Arrive prepared by planning your itinerary around the must-see historic sites to maximize your experience in this charming area.
  • Choose centrally located vacation rentals: Staying near the heart of downtown ensures easy access to the region’s iconic streets, shops, and dining options.
  • Take advantage of walking tours: Discover the city’s rich history on foot, allowing you to soak in the unique architecture and vibrant atmosphere firsthand.
  • Visit during off-peak hours: To enjoy a more relaxed visit and avoid crowds, plan your excursions early in the morning or later in the evening within this popular destination.

Transportation Options

  • Walking Tours: Exploring the area on foot is a popular way to immerse yourself in the historic charm and local culture of this destination.
  • Golf Cart Rentals: Rent a golf cart to leisurely navigate through the charming streets of the region, enjoying the sights at your own pace.
  • Public Transportation: Local buses provide convenient, budget-friendly transit options for getting around the downtown area and nearby attractions.
  • Taxi and Rideshare Services: Taxis and rideshare apps like Uber and Lyft offer quick, reliable transportation for exploring the region comfortably.

Local Customs Options

  • Greetings with a handshake or a nod: In the area, locals often greet visitors warmly with a handshake or friendly nod, reflecting the region’s Southern hospitality.
  • Respect for historic sites: When exploring here, it’s customary to show reverence by staying on designated paths and avoiding touching or defacing historic landmarks.
  • Engaging in local storytelling: You might find residents sharing stories about the region’s rich history, emphasizing the importance of listening respectfully and appreciating their cultural heritage.
  • Supporting local traditions and crafts: Participating in or purchasing from local artisans helps preserve the area's cultural customs and enhances your authentic experience here.

Frequently Asked Questions About Downtown Historic District?

2. How many vacation rentals have private pools in Downtown Historic District?

There are 206 vacation rentals with private pools near Downtown Historic District. Top-rated RBO homes that have access to a swimming pool include:

3. Which vacation homes in Downtown Historic District are best for families?

If you are looking for a family-friendly vacation home in Downtown Historic District, check out one of the following properties as all are highly-rated places to stay with excellent review for families or groups staying in Downtown Historic District:

4. How many Rentbyowner vacation rentals are available in Downtown Historic District?

Currently, the total number of properties listed by Rent By Owner in 2026 is over 3287 in the Downtown Historic District 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 Downtown Historic District. 

5. What is the cancellation policy for vacation rentals in this historic district?

Cancellation policies vary depending on the individual property owner. You should review the specific listing details or contact the host directly to understand the terms and any potential fees or penalties.

6. Are early check-in or late check-out options available at these downtown historic district properties?

Availability of early check-in or late check-out depends on the property and can be arranged with the host prior to your arrival. It's recommended to inquire about these options when booking or communicating with the property owner.

7. How do I find out about amenities included with my rental in this area?

Amenities are listed in each property’s description, but for detailed information or special requests, reaching out directly to the host ensures you have all necessary details before your stay.

8. What should I do if I encounter issues during my stay at a vacation rental?

If you experience any problems, contact the property owner or local management immediately. Most hosts are available to assist to ensure your visit remains comfortable and enjoyable.

9. Is parking available near vacation rentals in this region?

Parking options vary by property; some may include designated spots while others might require street parking. Check the listing details or ask the host to confirm parking arrangements before arriving.

Downtown Historic District Top Rated Vacation Rentals

Apartment
Map-icon
like-icon10.0
Exceptional
(170 Reviews)
2 Bedrooms 2 Baths 4 Guests 1300 ft²
  • Oceanfront
    Oceanfront
  • Parking
    Parking
More amenities
R4,988/Night 7 Nights - R34,921
House
like-icon10.0
Exceptional
(141 Reviews)
4 Bedrooms 3 Baths 8 Guests 3700 ft²
  • Private Pool
    Private Pool
  • Hot Tub
    Hot Tub
More amenities
R22,693/Night 7 Nights - R158,852
House
Map-icon
like-icon10.0
Exceptional
(130 Reviews)
5 Bedrooms 3 Baths 11 Guests 2800 ft²
  • Private Pool
    Private Pool
  • Oceanfront
    Oceanfront
More amenities
R17,900/Night 7 Nights - R125,302
House
Map-icon
like-icon10.0
Exceptional
(121 Reviews)
2 Bedrooms 2 Baths 5 Guests 700 ft²
  • Private Pool
    Private Pool
  • Parking
    Parking
More amenities
R6,951/Night 7 Nights - R48,658
Condo
Map-icon
like-icon10.0
Exceptional
(107 Reviews)
2 Bedrooms 2 Baths 4 Guests 1331 ft²
  • Oceanfront
    Oceanfront
  • Hot Tub
    Hot Tub
More amenities
R3,919/Night 7 Nights - R27,441
House
Map-icon
like-icon10.0
Exceptional
(106 Reviews)
8 Bedrooms 5 Baths 19 Guests
  • Private Pool
    Private Pool
  • Hot Tub
    Hot Tub
More amenities
R17,232/Night 7 Nights - R120,629
Condo
Map-icon
like-icon10.0
Exceptional
(100 Reviews)
2 Bedrooms 1 Bath 4 Guests
  • Oceanfront
    Oceanfront
  • Hot Tub
    Hot Tub
More amenities
R3,600/Night 7 Nights - R25,196
House
Map-icon
like-icon10.0
Exceptional
(82 Reviews)
2 Bedrooms 2 Baths 4 Guests 1200 ft²
  • Oceanfront
    Oceanfront
  • Parking
    Parking
More amenities
R4,707/Night 7 Nights - R32,956