Entire home

Cheerful Cottage in Ocala's Historic District

Photo gallery for Cheerful Cottage in Ocala's Historic District

A dining area with a wooden table, white chairs, a vase with greenery, and large windows with white curtains.
A living room with a fireplace, a television mounted above it, and a sofa.
A kitchen with white cabinets, a stainless steel sink, wooden countertops, and large windows with a view of trees.
A living room with a beige sofa, a white armchair, and a patterned rug. There are large windows with curtains, a chandelier, and a wall-mounted mirror.
A bedroom with a bed, nightstands, a ceiling fan, and a view of the outdoors.

Reviews

10 out of 10
Exceptional

Highlights

  • Made for relaxation
    Top-rated for comfort — guests feel right at home here.
  • Games
    A rare find - enjoy a variety of games available on-site.
  • Centrally-located
    You're never far from where you need to be with this convenient location.
  • Discover nearby landmarks
    Near Ocala Downtown Square

Popular amenities

  • Patio
  • Air-conditioning
  • Refrigerator
  • Internet
  • Washing machine
  • Onsite parking available

Explore the area

View in a map
Ocala, FL
  • Place, Ocala Downtown Square
    ‪14 min walk‬
  • Place, Tuscawilla Park
    ‪15 min walk‬
  • Place, Reilly Arts Center
    ‪4 min drive‬

Rooms & beds

2 bedrooms (sleeps 4)

Bedroom 1

1 Queen Bed

Bedroom 2

1 King Bed

1 bathroom

Bathroom 1

Toilet · Shower only

Spaces

Deck or patio
Kitchen

Add dates for prices

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About the area

Ocala

Located in Ocala, this cottage is in the city centre. The area's natural beauty can be seen at Ocala Downtown Square and Silver Springs State Park. Discovery Center and Reilly Arts Center 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 cycling.
View more Cottages in OcalaOpens in a new window
Map
Ocala, FL

What's nearby

  • Ocala Downtown Square - 14 min walk - 1.2 km
  • Tuscawilla Park - 15 min walk - 1.3 km
  • Reilly Arts Center - 4 min drive - 2.4 km
  • Discovery Center - 4 min drive - 2.4 km
  • World Equestrian Center – Ocala - 17 min drive - 20.2 km

Getting around

  • Ocala Station - 5 min drive
  • Gainesville, FL (GNV-Gainesville Regional) - 65 min drive

Restaurants

  • ‪Miller's Ale House - ‬17 min walk
  • ‪IHOP - ‬16 min walk
  • ‪Mellow Mushroom Ocala - ‬14 min walk
  • ‪Say Taco Tequila Bar & Grill - ‬16 min walk
  • ‪O'Malley's Alley - ‬15 min walk

Frequently asked questions

Is Cheerful Cottage in Ocala's Historic District pet-friendly?

No, pets are not allowed at this property.

How much does it cost to stay at Cheerful Cottage in Ocala's Historic District?

As of 29 Oct 2026, prices found for a 1-night stay for 2 adults at Cheerful Cottage in Ocala's Historic District on 11 Jan 2027 start from £410, including taxes and fees. This price is based on the lowest nightly price found in the last 24 hours for stays in the next 30 days. Prices are subject to change. Choose your dates for more accurate prices.

How much is parking at Cheerful Cottage in Ocala's Historic District?

On-site parking is available at the property.

What time is check-in at Cheerful Cottage in Ocala's Historic District?

Check-in begins at 4:00 PM.

What time is check-out at Cheerful Cottage in Ocala's Historic District?

Checkout is at 10:00 AM.

Where is Cheerful Cottage in Ocala's Historic District located?

Located in Historic District, this cottage is within a 15-minute walk of Ocala Downtown Square, Tuscawilla Park and AdventHealth Ocala. HCA Florida Ocala Hospital and Munroe Regional Medical Center are also within 1 mile (2 km). Ocala Station is 21 minutes by foot.

Reviews

10

Exceptional

Reviews are presented in chronological order, subject to a moderation process, and verified unless otherwise labelled.
Learn moreOpens in a new window
Rating 10 - Excellent. 48 out of 49 reviews
Rating 8 - Good. 1 out of 49 reviews
Rating 6 - Okay. 0 out of 49 reviews
Rating 4 - Poor. 0 out of 49 reviews
Rating 2 - Terrible. 0 out of 49 reviews

10/10

Cleanliness

10/10

Check-in

10/10

Communication

10/10

Location

10/10

Listing accuracy

Reviews

Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
Great place! Great location!
Stayed 3 nights in Sep 2026
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
Such a charming bungalow! It was the perfect location for a weekend getaway. The surrounding community is very well up-kept and the cottage itself is so perfect. We would definitely stay again.
Stayed 2 nights in Sep 2026
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
Really enjoyed our stay in Ocala. Super location in pretty historical downtown, and easy to come and go. Very comfortable, and quaint. Owners super to work with. Highly recommend.
Stayed 6 nights in Jul 2026
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, listing accuracy
Cute little cottage- a good 20 minute walk to the restaurants but a nice walk.
Stayed 2 nights in May 2026
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
Great location
Stayed 9 nights in Jan 2026
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
We are very thankful to enjoy this clean, cute property in a lovely neighborhood.
Stayed 5 nights in Feb 2026
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
The Ocala Cottage in the Historic District was absolutely as described. It has been beautifully renovated, was exceptionally clean, and provided a very comfortable stay.Crystal was an excellent host, always communicative, responsive, and helpful throughout our visit.One of the highlights was walking through the neighborhood and admiring the beautiful historic homes. Historic downtown Ocala is within walking distance and offers several great restaurants and places to explore.We also enjoyed visiting Silver Springs State Park, where we saw the famous wild monkeys and took a glass-bottom boat ride. The park has beautiful walking trails, and kayaking is also available for those wanting to explore the waterways.The outdoor space at the cottage was a wonderful bonus, and the covered private parking was greatly appreciated. The area was very quiet, making it easy to relax and enjoy our stay.We would definitely stay here again and highly recommend this property to anyone visiting Ocala and the surrounding area.
Stayed 7 nights in Oct 2026
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
Very clean cottage that is true to the pictures advertised. We thoroughly enjoyed our stay.
Stayed 5 nights in Dec 2025
Response from VrboOwner on 21 Feb 2026
Excited for your next stay!
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
Very clean home with great amenities. We enjoyed the property very much.
Stayed 3 nights in Feb 2026
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
Sunny & comfy, just as posted. Lovely neighborhood which makes you feel right at home. Definitely stay again.
Stayed 17 nights in Mar 2026
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
Excellent stay - well appointed, clean, convenient to historic area. Enjoyed it two weekends in a row.
Stayed 2 nights in Jul 2025
Response from VrboOwner on 21 Feb 2026
Hope to see you again!
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy

Great place

Home was perfect for our stay. Great location
Stayed 4 nights in Mar 2025
Response from VrboOwner on 20 Mar 2025
Thanks so much for sharing, we enjoyed hosting you.
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
We enjoyed our stay while in Ocala visiting family. The house was very clean and beautifully decorated during the holiday. We loved being able to walk to through the historic district and to the town square. Our hosts were very responsive and we would definitely stay again on our next visit.
Stayed 3 nights in Dec 2025
Response from VrboOwner on 21 Feb 2026
The location is why we bought the house! Glad you enjoyed!
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
This is the perfect location for anything you want to do in Ocala. Situated within blocks of downtown makes walking easy and a fun way to explore. The neighborhood is extremely quite. The home is well appointed with everything you need.
Stayed 5 nights in Apr 2026
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
Beautifully appointed - comfortable bungalow. Loved being near the historic downtown.
Stayed 4 nights in Jul 2025
Response from VrboOwner on 14 Jul 2025
Thanks so much for staying with us!
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
I have stayed at this cheery cottage three times now. Every single stay has been very enjoyable. The neighbourhood is quiet. The cottage beautifully appointed. Easy access to shopping and dinning out. Very quick response time. Very accommodating when I needed a place to stay quickly. I am beyond thankful for this cute place to stay.
Stayed 3 nights in Apr 2026
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
Our stay was amazing. No issues whatsoever. Host was responsive and friendly. The space had everything we needed and was super quiet neighborhood. Would highly recommend this place
Stayed 2 nights in Feb 2026
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
Nice house Easy to get in and clean
Stayed 3 nights in Jan 2026
Response from VrboOwner on 20 Jan 2026
Thanks so much for staying with us!
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
Very nicely decorated, clean, comfortable, light and bright. Kitchen well supplied, coffee pods for the Keurig a nice touch. Beds comfortable with black out curtains on the windows. Located in a nice neighborhood to walk and see other historic homes.
Stayed 2 nights in Mar 2026
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
The cottage was comfortable & quiet. The kitchen had all the accessories that we needed & everything was in great shape. The bedding was beautiful & comfortable. The location was minutes from the adorable downtown with great restaurants. It was within good distance from the Equestrian Center. I would stay again if in the area.
Stayed 4 nights in Feb 2026
Response from VrboOwner on 21 Feb 2026
Please come back soon!
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
Super cute amd cozy historic house in amazing historic neighborhood. Everyone raves about the stay. Kitchen was furnished, plenty of sheets, soap, shampoo etc. towels and blankets. We were a family of 4 female relatives and it was the perfect size for a long weekend. It was very quiet and safe and bonus - we loved saying hello to the neighbors sweet kitty 🖤
Stayed 3 nights in Mar 2026
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
My husband and I. stayed at this beautiful cottage along with my daughter and her husband. I cannot say enough about this cottage. There was plenty of room for the four of us and the beds were very comfortable. Now , every time I go to visit Ocala , this will be the place we stay. Quaint place near the Ocala sqare, where there us always events going on and somethingto do.. True Gem
Stayed 2 nights in Apr 2026
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
This cozy Ocala cottage was in the heart of the historic district and was full of charm. It was beautifully decorated, the amenities were exceptional, and immaculately clean! The host was so easy to work with, and made my stay extra great. An added benefit was the super comfy bed!
Stayed 2 nights in Sep 2025
Response from VrboOwner on 21 Feb 2026
Glad you liked the bed! Keep us in mind on your next visit.
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
Everything , crisp and fresh and all the little details. The shower head was particularly lovely. The drapes are gorgeous. And a really great neighborhood. And Communication was prompt.
Stayed 3 nights in Jan 2026
Response from VrboOwner on 21 Feb 2026
Let us known when you will be returning. We would love to host you again.
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
Very clean and well appointed. All our needs were met during our stay. Thank you!
Stayed 7 nights in Jul 2025
Response from VrboOwner on 21 Feb 2026
Thank you!
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