Entire home
Cottage Osceola – A Cozy Escape in Historic St. Augustine
Cottage near Flagler College in St. Augustine
Choose dates to view prices
Photo gallery for Cottage Osceola – A Cozy Escape in Historic St. Augustine





Reviews
1010 out of 10
Exceptional
Entire home
Popular amenities
- Parking available
- Laundry
- Pet-friendly
- Outdoor space
- Air conditioning
- Free WiFi
Explore the area

St. Augustine, FL
- Flagler CollegePlace, Flagler College5 min drive
- St. George StreetPlace, St. George Street6 min drive
- Castillo de San Marcos National MonumentPlace, Castillo de San Marcos National Monument7 min drive
- St. Augustine, FL (UST-Northeast Florida Regional)Airport, St. Augustine, FL (UST-Northeast Florida Regional)10 min drive
Room options
You may also like
Ad

Hilton Garden Inn St. Augustine Historic District
Uptown
- Pool
- Pet-friendly
- Free WiFi
- Restaurant
4.3 out of 5, Excellent, 392 reviews
4.3
Excellent
392 reviews
The price is CA $168
CA $168
CA $187 total
includes taxes & fees
Nov 13 - Nov 14
Ad

Homewood Suites by Hilton St. Augustine San Sebastian
Oyster Creek
- Pool
- Breakfast included
- Pet-friendly
- Free WiFi
4.4 out of 5, Excellent, 1,000 reviews
4.4
Excellent
1,000 reviews
The price is CA $157
CA $157
CA $175 total
includes taxes & fees
Nov 13 - Nov 14
Ad

Hilton Garden Inn St. Augustine Beach
St. Augustine
- Pool
- Hot tub
- Pet-friendly
- Free WiFi
4.0 out of 5, Very good, 1,002 reviews
4.0
Very good
1,002 reviews
The price is CA $146
CA $146
CA $162 total
includes taxes & fees
Nov 16 - Nov 17
Ad

Hampton Inn St. Augustine US1 North
Nelmar Terrace
- Pool
- Hot tub
- Breakfast included
- Pet-friendly
4.2 out of 5, Very good, 963 reviews
4.2
Very good
963 reviews
The price is CA $143
CA $143
CA $159 total
includes taxes & fees
Nov 9 - Nov 10
Ad

DoubleTree by Hilton Hotel St. Augustine Historic District
Uptown
- Pool
- Pet-friendly
- Free WiFi
- Restaurant
4.3 out of 5, Excellent, 1,002 reviews
4.3
Excellent
1,002 reviews
The price is CA $173
CA $173
CA $193 total
includes taxes & fees
Nov 12 - Nov 13
Ad

Hilton St. Augustine Historic Bayfront
St. Augustine Historic District
- Pool
- Hot tub
- Free WiFi
- Restaurant
4.6 out of 5, Wonderful, 1,003 reviews
4.6
Wonderful
1,003 reviews
The price is CA $331
CA $331
CA $370 total
includes taxes & fees
Nov 11 - Nov 12
Ad

Embassy Suites By Hilton St Augustine Beach-Oceanfront Resort
St. Augustine
- Pool
- Breakfast included
- Pet-friendly
- Free WiFi
4.4 out of 5, Excellent, 1,221 reviews
4.4
Excellent
1,221 reviews
The price is CA $200
CA $200
CA $258 total
includes taxes & fees
Nov 20 - Nov 21
Ad

Hampton Inn St. Augustine Beach
St. Augustine
- Pool
- Hot tub
- Breakfast included
- Pet-friendly
4.3 out of 5, Excellent, 1,002 reviews
4.3
Excellent
1,002 reviews
The price is CA $157
CA $157
CA $175 total
includes taxes & fees
Nov 16 - Nov 17
Ad

Hampton Inn St. Augustine-I-95
St. Augustine
- Pool
- Breakfast included
- Pet-friendly
- Parking included
4.1 out of 5, Very good, 818 reviews
4.1
Very good
818 reviews
The price is CA $117
CA $117
CA $131 total
includes taxes & fees
Nov 16 - Nov 17
Ad

Home2 Suites by Hilton St. Augustine I-95
St. Augustine
- Pool
- Breakfast included
- Pet-friendly
- Parking included
4.4 out of 5, Excellent, 1,000 reviews
4.4
Excellent
1,000 reviews
The price is CA $170
CA $170
CA $190 total
includes taxes & fees
Nov 13 - Nov 14
About the area
St. Augustine
Seaside stay .Within 3 miles (5 km) of this St. Augustine cottage, you'll find Royal St. Augustine Golf and Country Club and San Sebastian River. Hidden Harbor Marina and San Sebastian Winery are also within 3 miles (5 km).
What's nearby
- Flagler College - 5 min drive - 4.3 km
- St. George Street - 6 min drive - 5.3 km
- Lightner Museum - 6 min drive - 4.6 km
- Ponce de Leon's Fountain of Youth Archaeological Park - 6 min drive - 5.7 km
- Castillo de San Marcos National Monument - 7 min drive - 6.0 km
Getting around
- St. Augustine, FL (UST-Northeast Florida Regional) - 16 min drive
Restaurants
- Circle K - 4 min drive
- Bog Brewing Company - 4 min drive
- The Press - 4 min drive
- Maracuya - 4 min drive
- Buena Onda Cafe - 4 min drive
About this property
Entire place
You'll have the entire home to yourself and will only share it with other guests in your party.
Cottage Osceola – A Cozy Escape in Historic St. Augustine
Step into the charm of Old Florida with this beautifully remodeled 400 sq ft cottage, nestled in the heart of the West Augustine Historic District. Cottage Osceola is one of the original homes in the area, now thoughtfully updated to blend modern comfort with classic character — offering a peaceful and romantic escape just minutes from everything.
Whether you're here for a weekend getaway, a beach retreat, or to explore America’s oldest city, this tiny house has all you need. Located just 5 minutes from historic downtown St. Augustine and 10 minutes to the beach, it’s perfectly positioned for easy access while still offering quiet seclusion surrounded by nature.
Inside, you'll find a queen bed, a futon couch for extra sleeping space, and a compact but functional kitchenette featuring a coffee maker, mini-fridge, and microwave. Stay comfortable year-round with full HVAC, and enjoy streaming or remote work with high-speed WiFi.
Step outside to your private outdoor living area, complete with a fire pit and seating — perfect for winding down under the stars. Whether you’re sipping coffee in the morning sun or enjoying a glass of wine by the firelight, this space is made for relaxing.
Cottage Osceola offers a unique tiny home experience that’s both romantic and practical. Ideal for solo travelers, couples, or a pair of friends looking for something cozy, local, and full of charm.
Whether you're here for a weekend getaway, a beach retreat, or to explore America’s oldest city, this tiny house has all you need. Located just 5 minutes from historic downtown St. Augustine and 10 minutes to the beach, it’s perfectly positioned for easy access while still offering quiet seclusion surrounded by nature.
Inside, you'll find a queen bed, a futon couch for extra sleeping space, and a compact but functional kitchenette featuring a coffee maker, mini-fridge, and microwave. Stay comfortable year-round with full HVAC, and enjoy streaming or remote work with high-speed WiFi.
Step outside to your private outdoor living area, complete with a fire pit and seating — perfect for winding down under the stars. Whether you’re sipping coffee in the morning sun or enjoying a glass of wine by the firelight, this space is made for relaxing.
Cottage Osceola offers a unique tiny home experience that’s both romantic and practical. Ideal for solo travelers, couples, or a pair of friends looking for something cozy, local, and full of charm.
Similar properties

Casa Fuego | Private Spa Retreat
Casa Fuego | Private Spa Retreat
St. Augustine
- Hot tub
- Pet-friendly
- Free WiFi
- Air conditioning
The price is CA $126
CA $126
CA $325 total
includes taxes & fees
Nov 9 - Nov 10

La Casa Caliente - Spa | Romantic Tiny Retreat Near Beaches & Old Town
La Casa Caliente - Spa | Romantic Tiny Retreat Near Beaches & Old Town
St. Augustine
- Hot tub
- Kitchen
- Pet-friendly
- Free WiFi
The price is CA $140
CA $140
CA $344 total
includes taxes & fees
Nov 7 - Nov 8

Guy Harvey Resort on St Augustine Beach
Guy Harvey Resort on St Augustine Beach
St. Augustine
- Pool
- Pet-friendly
- Parking included
- Free WiFi
4.4 out of 5, Excellent, 2,721 reviews
4.4
Excellent
2,721 reviews
The price is CA $189
CA $189
CA $211 total
includes taxes & fees
Nov 13 - Nov 14

The Red Cottage ~ 5 min. stroll to Historic St. George Street - on site parking
The Red Cottage ~ 5 min. stroll to Historic St. George Street - on site parking
Uptown
- Kitchen
- Washer
- Pet-friendly
- Air conditioning
4.5 out of 5, Wonderful, 431 reviews
4.5
Wonderful
431 reviews

Mermaid relaxing studio with Pool
Mermaid relaxing studio with Pool
St. Augustine
- Pool
- Kitchen
- Free WiFi
- Air conditioning
4.9 out of 5, Exceptional, 45 reviews
4.9
Exceptional
45 reviews

Quaint Downtown Small Apt. Just Park Your car and Walk Everywhere in Town
Quaint Downtown Small Apt. Just Park Your car and Walk Everywhere in Town
Downtown Historic District
- Kitchen
- Washer
- Dryer
- Air conditioning
4.6 out of 5, Wonderful, 115 reviews
4.6
Wonderful
115 reviews
The price is CA $196
CA $196
CA $345 total
includes taxes & fees
Nov 9 - Nov 10

Just North of Historic St. Aug, Patio, Garage, BBQ
Just North of Historic St. Aug, Patio, Garage, BBQ
St. Augustine
- Kitchen
- Washer
- Dryer
- Pet-friendly
4.7 out of 5, Exceptional, 6 reviews
4.7
Exceptional
6 reviews

Close proximity to Vilano and St George
Close proximity to Vilano and St George
Greater Fullerwood
- Pet-friendly
- Free WiFi
- Air conditioning
- Outdoor space
4.5 out of 5, Wonderful, 19 reviews
4.5
Wonderful
19 reviews
The price is CA $169
CA $169
CA $294 total
includes taxes & fees
Nov 14 - Nov 15

Anderson Street Retreat
Anderson Street Retreat
St. Johns County
- Kitchen
- Pet-friendly
- Air conditioning
- Parking available
1.0 out of 5, 1 review
1.0
1 review

Adorable cottage central to everything
Adorable cottage central to everything
Ravenswood
- Kitchen
- Washer
- Dryer
- Free WiFi
5.0 out of 5, Exceptional, 115 reviews
5
Exceptional
115 reviews
The price is CA $182
CA $182
CA $371 total
includes taxes & fees
Nov 9 - Nov 10
Property amenities
Internet
- Available in the cottage: Free WiFi
Parking and transportation
- Car recommended
- Parking on site
Food and drink
- Coffee/tea maker
- Cookware, dishware, and utensils
- Microwave
- Refrigerator
- Spices
- Stovetop
- Toaster
Dining
- Dining table
Bedrooms
- Bedroom
- Bedsheets provided
Bathroom
- 1 bathroom
- Hair dryer
- Shower
- Towels provided
Living spaces
- Dining table
- Living room
Entertainment
- Smart TV
Outdoor areas
- Balcony
- Firepit
- Garden
Laundry
- Laundry facilities
Comfort
- Air conditioning
- Heating
Pets
- Pet friendly
Suitability/Accessibility
- Smoking not allowed
Location highlights
- In a rural location
- In the city center
- Near a health/beauty spa
- Near a hospital
- Near an outlet shopping mall
- Near the marina
- Near the sea
Things to do
- Casino nearby
- Cycling nearby
- Fishing nearby
- Golfing nearby
- Hiking nearby
- Horseback riding nearby
- Kayaking nearby
- Motor boating nearby
- Parasailing nearby
- Sailing nearby
- Scuba diving nearby
- Snorkeling nearby
- Surfing/bodyboarding nearby
- Swimming nearby
- Water skiing nearby
- Wildlife walks nearby
- Windsurfing nearby
- Winery tours nearby
Safety features
- Carbon monoxide detector (host has indicated there is a carbon monoxide detector on the property)
- Smoke detector (host has indicated there is a smoke detector on the property)
- First aid kit
- Fire extinguisher
General
- Garden
- Unit size: 360 square feet
Policies
Check-in
Check-in time starts at 3:00 PM
Contactless check-in available
Minimum check-in age: 26
Check-out
Check-out before 10:00 AM
Special check-in instructions
You will receive an email from the host with check-in and check-out instructions
Pets
- Pets are welcome
- Service animals are exempt from fees
- Note from host: Only one dog is allowed there is a pet fee.
Children and extra beds
- Children are welcome.
Events
No events allowed
Smoking
Smoking is not permitted
Important information
You need to know
Extra-person charges may apply and vary depending on property policy
Government-issued photo identification and a credit card, debit card, or cash deposit may be required at check-in for incidental charges
Special requests are subject to availability upon check-in and may incur additional charges; special requests cannot be guaranteed
Onsite parties or group events are strictly prohibited
Host has indicated there is a carbon monoxide detector on the property
Host has indicated there is a smoke detector on the property
Safety features at this property include a fire extinguisher and a first aid kit
This property is managed through our partner, Vrbo. You will receive an email from Vrbo with a link to a Vrbo account, where you can change or cancel your reservation
Charges for extra guests may apply and vary according to property policy.
A cash deposit, credit card, or debit card for incidental charges and government-issued photo identification may be required upon check-in.
Special requests are subject to availability at the time of check-in. Special requests can't be guaranteed and may incur additional charges.
A cash deposit, credit card, or debit card for incidental charges and government-issued photo identification may be required upon check-in.
Special requests are subject to availability at the time of check-in. Special requests can't be guaranteed and may incur additional charges.
- This property is managed by a professional host. The provision of housing is linked to their trade, business, or profession. Onsite parties or group events are strictly prohibited. For guests' safety, the property includes a carbon monoxide detector, a fire extinguisher, a smoke detector, and a first aid kit in each accommodation.
Property is also known as
orp5b6edf3x