Old Town Holiday Rentals
- St. Augustine
- ·
- Downtown Historic District
- 0.46 mi to center
- Parking
- Kitchen
- Internet
- Pet Friendly
- St. Augustine
- ·
- Downtown Historic District
- 0.09 mi to center
- Parking
- View
- Air Conditioner
- Internet
- Florida
- ·
- St. Augustine
- 1.69 mi to center
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
- St. Augustine
- ·
- Downtown Historic District
- 0.18 mi to center
- Oceanfront
- Parking
- Ocean View
- Balcony/Terrace
- Florida
- ·
- St. Augustine
- 2.12 mi to center
- Parking
- Air Conditioner
- Internet
- Security/Safety
- St. Augustine
- ·
- Downtown Historic District
- 0.18 mi to center
- Oceanfront
- Parking
- Ocean View
- Balcony/Terrace
- St. Augustine
- ·
- Lincolnville
- 0.07 mi to center
- Parking
- Kitchen
- Air Conditioner
- Internet
- Florida
- ·
- St. Augustine
- 1.02 mi to center
- Oceanfront
- Parking
- Ocean View
- Balcony/Terrace
- Florida
- ·
- St. Augustine
- 1.26 mi to center
- Oceanfront
- Parking
- Ocean View
- Balcony/Terrace
Luxury Holiday Rentals in Old Town
- St. Augustine
- ·
- Downtown Historic District
- 0.21 mi to center
- Private Pool
- Parking
- Pool
- Ocean View
- St. Augustine
- ·
- Vilano Beach
- 1.41 mi to center
- Oceanfront
- Hot Tub
- Parking
- Spa
- St. Augustine
- ·
- St. Augustine Historic District
- 0.19 mi to center
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
- St. Augustine
- ·
- Downtown Historic District
- 0.36 mi to center
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
- Florida
- ·
- St. Augustine
- 1.06 mi to center
- Private Pool
- Oceanfront
- Hot Tub
- Parking
- Florida
- ·
- St. Augustine
- 0.22 mi to center
- Parking
- Pool
- Balcony/Terrace
- Kitchen
- St. Augustine
- ·
- Vilano Beach
- 1.05 mi to center
- Oceanfront
- Parking
- Ocean View
- Balcony/Terrace
- St. Augustine
- ·
- Lincolnville
- 0.20 mi to center
- Oceanfront
- Hot Tub
- Parking
- Pool
- St. Augustine
- ·
- Downtown Historic District
- 0.21 mi to center
- Private Pool
- Parking
- Pool
- Ocean View
Top-Rated Holiday Rentals with a Pool in Old Town
- St. Augustine
- ·
- Vilano Beach
- 1.30 mi to center
- Private Pool
- Parking
- Pool
- Ocean View
- St. Augustine
- ·
- Lincolnville
- 0.11 mi to center
- Oceanfront
- Parking
- Pool
- Ocean View
- St. Augustine
- ·
- Downtown Historic District
- 0.23 mi to center
- Private Pool
- Hot Tub
- Parking
- Pool
- Florida
- ·
- St. Augustine
- 1.36 mi to center
- Private Pool
- Oceanfront
- Parking
- Pool
- St. Augustine
- ·
- Vilano Beach
- 1.30 mi to center
- Oceanfront
- Parking
- Pool
- Ocean View
- Florida
- ·
- St. Augustine
- 0.33 mi to center
- Private Pool
- Parking
- Pool
- Ocean View
- St. Augustine
- ·
- Vilano Beach
- 1.30 mi to center
- Parking
- Pool
- Ocean View
- Balcony/Terrace
- St. Augustine
- ·
- Vilano Beach
- 1.07 mi to center
- Private Pool
- Oceanfront
- Hot Tub
- Pool
- St. Augustine
- ·
- Lincolnville
- 0.04 mi to center
- Oceanfront
- Parking
- Pool
- Ocean View
Pet-Friendly Holiday Rentals in Old Town
- St. Augustine
- ·
- Downtown Historic District
- 0.18 mi to center
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
- Florida
- ·
- St. Augustine
- 0.93 mi to center
- Parking
- Air Conditioner
- Internet
- Pet Friendly
- St. Augustine
- ·
- Vilano Beach
- 0.96 mi to center
- Oceanfront
- Parking
- Ocean View
- Balcony/Terrace
- Florida
- ·
- St. Augustine
- 1.69 mi to center
- Parking
- Kitchen
- Air Conditioner
- Internet
- St. Augustine
- ·
- Lincolnville
- 0.19 mi to center
- Oceanfront
- Parking
- Spa
- Ocean View
- Florida
- ·
- St. Augustine
- 0.95 mi to center
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
- St. Augustine
- ·
- Downtown Historic District
- 0.41 mi to center
- Oceanfront
- Parking
- Ocean View
- Balcony/Terrace
- Florida
- ·
- St. Augustine
- 3.25 mi to center
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
- Florida
- ·
- St. Augustine
- 1.67 mi to center
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
Large Holiday Rentals and Private Villas in Old Town
- St. Augustine
- ·
- Vilano Beach
- 1.00 mi to center
- Hot Tub
- Parking
- Pool
- Ocean View
- St. Augustine
- ·
- Downtown Historic District
- 0.14 mi to center
- Parking
- Air Conditioner
- Internet
- Child Friendly
- St. Augustine
- ·
- Downtown Historic District
- 0.39 mi to center
- Oceanfront
- Parking
- Ocean View
- Balcony/Terrace
- St. Augustine
- ·
- Vilano Beach
- 0.93 mi to center
- Private Pool
- Parking
- Pool
- Kitchen
- Florida
- ·
- St. Augustine
- 0.15 mi to center
- Parking
- View
- Air Conditioner
- Internet
- Florida
- ·
- St. Augustine
- 3.29 mi to center
- Hot Tub
- Parking
- Balcony/Terrace
- Kitchen
- St. Augustine
- ·
- Vilano Beach
- 0.60 mi to center
- Air Conditioner
- Internet
- Child Friendly
- Laundry
- Florida
- ·
- St. Augustine
- 1.31 mi to center
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
- Florida
- ·
- St. Augustine
- 1.00 mi to center
- Parking
- Ocean View
- Balcony/Terrace
- View
Wheelchair Accessible Holiday Homes in Old Town
- Florida
- ·
- St. Augustine
- 0.95 mi to center
- Private Pool
- Oceanfront
- Parking
- Pool
- Florida
- ·
- St. Augustine
- 0.91 mi to center
- Parking
- Internet
- Child Friendly
- Wheelchair Accessible
- St. Augustine
- ·
- Vilano Beach
- 1.55 mi to center
- Breakfast
- Parking
- Pool
- Balcony/Terrace
- St. Augustine
- ·
- Vilano Beach
- 1.29 mi to center
- Oceanfront
- Parking
- Pool
- Ocean View
- Florida
- ·
- St. Augustine
- 1.80 mi to center
- Oceanfront
- Parking
- Ocean View
- View
- Florida
- ·
- St. Augustine
- 1.31 mi to center
- Oceanfront
- Parking
- Pool
- Ocean View
- St. Augustine
- ·
- St. Augustine Beach
- 0.50 mi to center
- Private Pool
- Hot Tub
- Parking
- Pool
- St. Augustine
- ·
- St. Augustine Historic District
- 0.08 mi to center
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
- St. Augustine
- ·
- Vilano Beach
- 1.29 mi to center
- Oceanfront
- Parking
- Pool
- Ocean View
Old Town Private Villas and Holiday Homes Under $200
- Florida
- ·
- St. Augustine
- 1.05 mi to center
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
- Florida
- ·
- St. Augustine
- 1.81 mi to center
- Oceanfront
- Parking
- Ocean View
- Balcony/Terrace
- St. Augustine
- ·
- Downtown Historic District
- 0.39 mi to center
- Breakfast
- Ocean View
- View
- Air Conditioner
- Florida
- ·
- St. Augustine
- 1.41 mi to center
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
- Florida
- ·
- St. Augustine
- 1.64 mi to center
- Parking
- Air Conditioner
- Internet
- Pet Friendly
- St. Augustine
- ·
- Downtown Historic District
- 0.03 mi to center
- Parking
- Kitchen
- Air Conditioner
- Internet
- Florida
- ·
- St. Augustine
- 2.14 mi to center
- Balcony/Terrace
- Kitchen
- Air Conditioner
- Internet
- Florida
- ·
- St. Augustine
- 0.27 mi to center
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
- Florida
- ·
- St. Augustine
- 1.04 mi to center
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
Instantly Bookable Holiday Homes in Old Town
- St. Augustine
- ·
- Downtown Historic District
- 0.14 mi to center
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
- Florida
- ·
- St. Augustine
- 0.70 mi to center
- Hot Tub
- Parking
- Kitchen
- Air Conditioner
- St. Augustine
- ·
- Downtown Historic District
- 0.14 mi to center
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
- St. Augustine
- ·
- Downtown Historic District
- 0.14 mi to center
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
- Florida
- ·
- St. Augustine
- 0.70 mi to center
- Hot Tub
- Parking
- Kitchen
- Air Conditioner
- St. Augustine
- ·
- Downtown Historic District
- 0.14 mi to center
- Parking
- Kitchen
- Air Conditioner
- Laundry
- Florida
- ·
- St. Augustine
- 0.82 mi to center
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
- Florida
- ·
- St. Augustine
- 1.31 mi to center
- Oceanfront
- Parking
- Pool
- Ocean View
- Florida
- ·
- St. Augustine
- 1.89 mi to center
- Parking
- Kitchen
- Air Conditioner
- Internet
Book a Last Minute Place to Stay in Old Town
About Casai's Private Villas and Holiday Rentals in Old Town
Discover more than 2887 vacation rentals available in Old Town. These rentals, ranging from vacation rentals to Casai Homes and other short-term private accommodations, offer top-notch amenities with unbeatable value, ensuring both comfort and luxury. Enjoy more space and value when you stay at a Casai property in Old Town.
Seeking last-minute deals or the best available offers for cottages, condos, private villas, and spacious vacation homes? With Casai in Old Town, you can effortlessly compare various deals with just a click. Whether you're looking for a Casai with exceptional swimming pools, hot tubs, pet-friendly options, or large master suite bedrooms equipped with large screen televisions, you'll find a variety of options near Old Town. On average, places to stay near Old Town offer 1020.89 ft², with nightly prices averaging US $348.
With Casai, finding and comparing holiday rentals in Old Town is easy and secure, often at a 30-40% discount compared to hotel prices. Simply search for your destination and secure your reservation today.
Top Accommodation Types in Old Town
| Type | Count |
|---|---|
| Vacation Homes | 1934 |
| Holiday Apartments | 490 |
| Cottages | 94 |
| Villas | 14 |
Use these Quick Filters to Find a Holiday Rental in Old Town
★ Pro Tip: Casai simplifies the process of comparing the finest listings across various online vacation rental platforms, including Booking.com and more. Utilize the Advanced Filter feature located at the top to effortlessly switch between Casai homes, vacation rentals, bed and breakfasts, private Airbnb-style rentals, eco-friendly properties, and different property types. Explore various cancellation policies, prices, and numerous options to find the ideal accommodation for your next vacation in Old Town.
Weather in Old Town, FL
View the weather forecast for Old Town before booking your Old Town Vacation Rentals to confirm your best time to go.
Other Places to Stay in Old Town, FL
Frequently Asked Questions About Old Town?
What are the top holiday rentals in Old Town?
With numerous options available in Old Town, planning to stay in the area? Consider booking a few nights at one of these properties, rated as the Top Holiday Rentals in Old Town:
- MARINA SUNSETS - SAINT AUGUSTINE DOWNTOWN HISTORIC DISTRICT
- A WOW! Pristine, private oceanfront. Luxury 7 unit boutique bldg. St Aug close
- Oceanfront Luxury Next To St Augustine Center - Quiet Vilano Beach, Dogs Welcome
- C2 Perfect location in historic city center, near beaches, patio, free parking!
- Walk to EVERYTHING Downtown within minutes. Shotgun House in Lincolnville.
- C6, Romantic apartment in city center, Flagler location, near beaches, parking!
- Dog-friendly renovated downtown apt FREE BIKES
- Ocean Front Condo W/private Beach Access & Minutes From Downtown St. Augustine
- Center of Historic City- Balcony Overlooks Shops, Restaurants, Bars, Free Parking, Walk Everywhere!
- Boathouse Cottage, Historic District, Private Pier, 1 Block to Trolley & Fort
How many holiday rentals have private pools in Old Town?
Discover a selection of holiday rentals with private pools near Old Town with Casai. Experience the epitome of luxury and relaxation in our top-rated villas and holiday homes, where you can enjoy exclusive access to refreshing swimming pools.
- Private Pool Oasis Near Beach + Downtown
- Holiday Inn Express St. Augustine - Vilano Beach by IHG
- NEW! Heated Pool, FirePit, Game Rm, Walk to Amp.
- Historic Downtown Home with Private Heated Pool! Walk to Everything!
Which holiday homes in Old Town are best for families?
If you're searching for a family-friendly holiday home in Old Town, consider one of the following properties. Each comes highly recommended, with excellent reviews for families or groups staying in Old Town:
- Brand New! Swim Spa, Fire Pit, Game Room, Downtown Historic District, $300 in Free Tickets!
- Steps to Ice Plant in Historic St Aug Upscale
- Lower Level 1 Block From 2 Beaches W/private Pool, High-speed Wi-fi
How many Casai.com holiday rentals are available in Old Town?
As of 2026, Casai boasts over 2887 properties listed in the Old Town area, with more being added continually. By consolidating listings from various websites, Casai provides an extensive selection of the finest Casai properties in Old Town.
Nearby Neighborhood (3)
| Neighborhood | Property Count |
|---|---|
| Downtown Historic District Vacation Rentals in St. Augustine, Florida | 1760 |
| St. Augustine Historic District Vacation Rentals in St. Augustine, Florida | 1321 |
| Lincolnville Vacation Rentals in St. Augustine, Florida | 439 |







































































