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Cheerful Cottage in Ocala's Historic District

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

Reviews

10 out of 10
Exceptional

Entire home

2 bedrooms1 bathroomSleeps 4884 sq ft

Popular amenities

  • Kitchen
  • Washer
  • Dryer
  • Air conditioning
  • Outdoor Space
  • Parking available

Explore the area

View in a map
Ocala, FL
  • Place, Ocala Downtown Square
    ‪14 min walk‬
  • Place, Juniper Prairie Wilderness
    ‪18 min walk‬
  • Place, Reilly Arts Center
    ‪4 min drive‬

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About the neighborhood

Ocala

Located in Historic District, this cottage is a leisurely stroll from sights such as Ocala Downtown Square and Tuscawilla Park. The cottage includes a kitchen, a patio, and a refrigerator.
View more Cottages in OcalaOpens in a new window

What's nearby

  • Ocala Downtown Square - 14 min walk - 0.8 miles
  • Tuscawilla Park - 15 min walk - 0.9 miles
  • Juniper Prairie Wilderness - 18 min walk - 1.0 mile
  • Reilly Arts Center - 4 min drive - 1.5 miles
  • Discovery Center - 4 min drive - 1.5 miles

Getting around

  • Ocala Station - 5 min drive
  • Gainesville Regional Airport (GNV) - 57 min drive

Restaurants

  • ‪Wawa - ‬13 min walk
  • ‪IHOP - ‬16 min walk
  • ‪Miller's Ale House - ‬17 min walk
  • ‪Mellow Mushroom Ocala - ‬14 min walk
  • ‪Say Taco Tequila Bar & Grill - ‬16 min walk

About this property

Entire place

You'll have the entire home to yourself and will only share it with other guests in your party.

Cheerful Cottage in Ocala's Historic District

Freshly renovated in chic style this 1934 is located in Ocala’s Historic District. Just a short walk to Ocala’s Downtown square. This serene home features beautiful green views, natural lighting, a cozy living space, king size bed, queen size bed and fast and free WiFi. furnished with everything you need for a comfortable and relaxing stay. Enjoy your morning coffee in a rocker on the sunny patio.
The cottage is air-conditioned and features a kitchen and a patio, and there's space to spread out with 2 bedrooms. Other standard amenities include a washing machine, a coffee maker, and an ironing board.

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Property amenities

Internet

  • Available in the cottage: WiFi

Parking and transportation

  • Wheelchair-accessible parking available

Kitchen

  • Coffee/tea maker
  • Cookware, dishware, and utensils
  • Dishwasher
  • Ice maker
  • Oven
  • Paper towels
  • Refrigerator
  • Stovetop
  • Toaster

Dining

  • Dining table

Bedrooms

  • 2 bedrooms
  • Bedsheets provided

Bathroom

  • 1 bathroom
  • Hair dryer
  • Shampoo
  • Shower
  • Soap
  • Toilet paper
  • Towels provided

Living spaces

  • Dining table
  • Living room

Entertainment

  • Games
  • Smart TV

Outdoor areas

  • Patio

Laundry

  • Laundry facilities
  • Washing machine

Comfort

  • Air conditioning
  • Heating

Pets

  • No pets allowed

Suitability/Accessibility

  • If you have requests for specific accessibility needs, please contact the property using the information on the reservation confirmation received after booking.
  • 1 accessible parking space
  • No elevator
  • Wheelchair-accessible parking
  • Smoking not allowed

Services and conveniences

  • Iron/ironing board

Location highlights

  • In the city center
  • Near a health/beauty spa
  • Near a hospital

Things to do

  • Golfing nearby
  • Hiking/biking trails nearby
  • Horseback riding nearby
  • Kayaking nearby
  • Mountain biking nearby
  • Scuba diving nearby
  • Snorkeling nearby
  • Swimming nearby
  • Water tubing 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)
  • Fire extinguisher

General

  • Property does not allow children
  • Unit size: 884 square feet

Policies

Check-in

Check-in time starts at 4:00 PM
Contactless check-in available
Minimum check-in age: 25

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
Information provided by the property may be translated using automated translation tools

Pets

  • This property doesn't allow pets

Children and extra beds

  • This property doesn't allow children

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
This property has outdoor spaces, such as balconies, patios, terraces which may not be suitable for children; if you have concerns, we recommend contacting the property prior to your arrival to confirm they can accommodate you in a suitable room
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
  • Check-in: 4:00 PM
  • Check-out: 10:00 AM
  • Minimum check-in age: 25

We should mention

Details about charges, deposits, or other important information:

  • This property is managed by a private host, not a professional engaged in trade or business.
  • This property has outdoor spaces, such as balconies, patios, terraces which may not be suitable for children. If you have concerns, we recommend contacting the property prior to your arrival to confirm they can accommodate you in a suitable room.
  • Charges for extra guests may apply and vary depending on the property's policy.
  • A cash deposit, credit card, or debit card for incidental charges, as well as a government-issued photo ID, may be required at check-in.
  • Special requests are subject to availability at the time of check-in and can't be guaranteed. Certain requests may come with additional charges.
  • Onsite parties or group events are strictly prohibited.
  • Onsite safety features include a carbon monoxide detector, a fire extinguisher, and a smoke detector.

Additional information about polices, regulations, and more:

  • There are no elevators.

Frequently asked questions

What can I see near this cottage?

This cottage is situated in Historic District within a short 14-minute walk of Ocala Downtown Square and also 14 minutes on foot from Tuscawilla Park. You'll also find Southeastern Livestock Pavilion SELP and Paddock Mall within a short drive.

Is parking available on site at Cheerful Cottage in Ocala's Historic District?

Yes, there is wheelchair-accessible parking available.

Is this cottage next to a casino?

No, this cottage is not connected to a casino.

Will I find an indoor pool at this cottage?

No, there is no indoor pool at this cottage.

What will couples enjoy most about a stay at Cheerful Cottage in Ocala's Historic District?

Couples will appreciate amenities at this cottage, including a smart TV and a kitchen in each cottage and a kitchen in some.

Are there hot tubs at Cheerful Cottage in Ocala's Historic District?

No, this cottage doesn't have a spa tub.

Does this cottage include breakfast service?

No, this cottage doesn't offer breakfast.

Does this cottage allow pets to stay for free?

No, pets aren't allowed at this cottage.

Are there connecting rooms at Cheerful Cottage in Ocala's Historic District?

No, there aren't connecting guestrooms at this cottage.

Are there rooms with balconies that I can book at Cheerful Cottage in Ocala's Historic District?

Yes, every cottage at Cheerful Cottage in Ocala's Historic District comes with a patio.

Cheerful Cottage in Ocala's Historic District Reviews

Reviews

10

Exceptional

Rating 10 - Excellent. 42 out of 43 reviews
Rating 8 - Good. 1 out of 43 reviews
Rating 6 - Okay. 0 out of 43 reviews
Rating 4 - Poor. 0 out of 43 reviews
Rating 2 - Terrible. 0 out of 43 reviews

10/10

Cleanliness

Reviews

Verified

10/10 Excellent

Lori S.

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

10/10 Excellent

Kendra O.

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

10/10 Excellent

Elaine T.

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

10/10 Excellent

Kendra O.

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
Verified

10/10 Excellent

Robert S.

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

10/10 Excellent

Anne D.

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
Verified

10/10 Excellent

Brooke T.

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

10/10 Excellent

Kari J.

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

10/10 Excellent

Andrea P.

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

10/10 Excellent

Melissa S.

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

10/10 Excellent

Nicole B.

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
Verified

10/10 Excellent

Deb W.

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
Verified

10/10 Excellent

Jennifer w.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Nice house Easy to get in and clean
Stayed 3 nights in Jan 2026
Verified

10/10 Excellent

Colby B.

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

Great place

Home was perfect for our stay. Great location
Stayed 4 nights in Mar 2025
Verified

10/10 Excellent

Nicole B.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Beautifully appointed - comfortable bungalow. Loved being near the historic downtown.
Stayed 4 nights in Jul 2025
Verified

10/10 Excellent

Marianne W.

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
Verified

10/10 Excellent

yvette m.

Liked: Cleanliness, check-in, communication, location, listing accuracy
We loved the location and the charm of the cottage. The neighborhood is quiet and this is something that we appreciated. In addition, the bedrooms have blackout drapes and that makes for a good nights sleep.Definitely would stay here again. The responsiveness of the owners was fantastic. When we arrived, the AC was not generating cold air. A quick text with Chris, and within an hour a tech was there fixing it while we were at dinner. We came back to a totally chill environment.
Stayed 2 nights in Apr 2026
Verified

10/10 Excellent

Kathryn B.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Cleaniness and responsiveness
Stayed 3 nights in Feb 2026
Verified

10/10 Excellent

Robin B.

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
Verified

10/10 Excellent

Louann D.

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
Verified

10/10 Excellent

Mary Paul H.

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

Relaxing

Very nice classic home,appreciated the very clean proprety and comfort of it as well.We would stay there again.
Stayed 5 nights in Apr 2025
Verified

8/10 Good

Deborah S.

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

Nicely done

Good location
Stayed 3 nights in Jan 2025
Verified

10/10 Excellent

Lori M.

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

Cute cottage - would stay again!

This rental property is just as pictured. It’s really cute, clean and everything you need to be comfortable. The host is responsive and accommodating. It’s also a perfect location and close to all the downtown restaurants and shopping. I highly recommend and would stay again.
Stayed 3 nights in May 2025
Verified

10/10 Excellent

Jamie H.

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

Perfect house and location

This property was perfect for our weekend stay. The location was convenient with a very quiet neighborhood. We would definitely stay here again if we visit ocala in the future. The checkin process was easy and everything we needed was there. weneeded was
Stayed 2 nights in Apr 2025
Verified

10/10 Excellent

Suzanne N.

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

Amazing Cottage

Well appointed, great location, lovely decorative touches, and a historic fairy tale feel to the home. Comfortable beds and plenty of coffee. Would live here! Loved it.
Stayed 3 nights in Apr 2025