Entire home

Cottage Osceola – A Cozy Escape in Historic St. Augustine

Photo gallery for Cottage Osceola – A Cozy Escape in Historic St. Augustine

Living Room / Kitchenette
Living Room / Kitchenette
Living Room
Living Room / Kitchenette
Living Room / Kitchenette
1 bedroom1 bathroomSleeps 3360 sq ft

Popular amenities

  • Parking available
  • Laundry
  • Pet-friendly
  • Air conditioning
  • Outdoor space
  • Free WiFi

Explore the area

Map
St. Augustine, FL
  • Flagler College
    ‪5 min drive‬
  • St. George Street
    ‪6 min drive‬
  • Castillo de San Marcos National Monument
    ‪8 min drive‬
  • St. Augustine, FL (UST-Northeast Florida Regional)
    ‪11 min drive‬

Rooms & beds

1 bedroom (sleeps 3)

Bedroom 1

1 Queen Bed and 1 Double Sofa Bed

1 bathroom

Bathroom 1

Toilet · Shower only

Spaces

Deck or patio
Balcony
Garden
Dining area

About this property

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.

Property manager

Greg Tanacea

Languages

English

Add dates for prices

Amenities

Pet-friendly
Free WiFi
Air conditioning
Laundry
Outdoor space
Parking available

Have a question?

AI iconBeta

Get instant answers with AI powered search of property information and reviews.

Similar properties

House Rules

Check in after 3:00 PM
Minimum age to rent: 26
Check out before 10:00 AM
default

Children

Children allowed: ages 0–17
default

Events

No events allowed
default

Pets

Pets allowed
We only allow dogs and there is a one time pet fee
default

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
On-site parties or group events are strictly prohibited
Host has indicated that there is a carbon monoxide detector on the property
Host has indicated that there is a smoke detector on the property
Safety features at this property include a fire extinguisher and a first aid kit

We should mention

A car is recommended for transport to and from this property

About the area

St. Augustine

Located in St. Augustine, this holiday home is in the city centre and by the sea. Castillo de San Marcos National Monument is a notable landmark, and the area's natural beauty can be seen at St. Augustine Beach and Vilano Beach. World Golf Village and Bayfront Carpet Golf are also worth visiting. Discover the area's water adventures with kayaking and scuba diving nearby, or enjoy the great outdoors with horse riding and hiking.
Map
St. Augustine, FL

What's nearby

  • Flagler College - 5 min drive - 4.0 km
  • Lightner Museum - 6 min drive - 4.3 km
  • St. George Street - 6 min drive - 4.6 km
  • Ponce de Leon's Fountain of Youth Archaeological Park - 7 min drive - 5.0 km
  • Castillo de San Marcos National Monument - 8 min drive - 4.9 km

Getting around

  • St. Augustine, FL (UST-Northeast Florida Regional) - 16 min drive

Restaurants

  • ‪McDonald's - ‬6 min drive
  • ‪Carmelo's Pizzeria - ‬5 min drive
  • ‪San Sebastian Winery - ‬5 min drive
  • ‪Bog Brewing Company - ‬4 min drive
  • ‪The Back 40 Urban Cafe - ‬5 min drive

Frequently asked questions

Is Cottage Osceola – A Cozy Escape in Historic St. Augustine pet-friendly?

Yes, pets are allowed at this property.

What time is check-in at Cottage Osceola – A Cozy Escape in Historic St. Augustine?

Check-in begins at 3:00 PM.

What time is check-out at Cottage Osceola – A Cozy Escape in Historic St. Augustine?

Checkout is at 10:00 AM.

Where is Cottage Osceola – A Cozy Escape in Historic St. Augustine located?

Located in the heart of St. Augustine, this holiday home is 1 mi (1.6 km) from Royal St. Augustine Golf and Country Club and within 3 miles (5 km) of San Sebastian River and Hidden Harbor Marina. San Sebastian Winery and Whetstone Chocolate Factory are also within 3 miles (5 km).

Reviews

Rating 10 - Excellent. 0 out of 0 reviews
Rating 8 - Good. 0 out of 0 reviews
Rating 6 - Okay. 0 out of 0 reviews
Rating 4 - Poor. 0 out of 0 reviews
Rating 2 - Terrible. 0 out of 0 reviews

Reviews

No reviews yet

Be the first to leave a review for this property after your stay.

About the host

Hosted by Greg Tanacea

Host profile image
Hi, I’m Greg! I’m a Navy submarine veteran with a deep love for the outdoors and a passion for creating unique, comfortable spaces for people to relax and recharge. I’ve been hosting vacation rentals for over 8 years and take pride in providing welcoming, well-appointed stays that feel like a true escape — whether you're here to explore nature, the beach, or the charm of historic St. Augustine. I look forward to hosting you at Cottage Osceola and helping you make memories that last!

Why they chose this property

Cottage Osceola is the perfect romantic escape for couples who love charm, comfort, and a touch of nature — and want to bring their furry companion along. Tucked into St. Augustine’s historic West Augustine district, this tiny cottage blends vintage character with modern touches like WiFi, HVAC, and a cozy outdoor fire pit. You’re just minutes from downtown restaurants and nightlife, yet far enough to enjoy peaceful evenings under the stars. With a private yard, pet-friendly policies, and everything you need to relax or explore, Cottage Osceola is your intimate home away from home.

What makes this property unique

Cozy and romantic tiny home, perfect for couples
One of the original homes in the historic West Augustine district
Pet-friendly with private outdoor space for you and your pup
Just 5 minutes to downtown St. Augustine and 10 minutes to the beach
Peaceful setting surrounded by nature with a private fire pit and outdoor seating
Fully equipped with HVAC, WiFi, queen bed, futon, and kitchenette

Languages:

English
Tell us how we can improve our siteShare feedback