Pet-friendly holiday rentals in Jefferson County

Private 2 Bedroom Cabana

Extra Spacey, Cozy and fully furnished second story 2 Bedroom (queen size beds) private home all to yourself. Spacious and light with an enclosed screened front porch overlooking the beautiful pasture and rolling hills of North Florida. . Private parking and entrance. All amenities to make your stay quiet and pleasant. We are 9 miles east of Monticello and just a few minutes from kayaking and canoeing on the Wacissa River. 35 minutes to Tallahassee and 20min to Thomasville , GA

Guest house, Hot tub & King Bed on Gated Property!

Please read all check-in notes! Near Hwy 19 i10 exit- 2 exits East of Florida's Capitol. Historic Downtown featuring large ole Southern homes — famous for ghost tours! Message for any questions! Please add any pet to booking! You won't have control of thermostat, but keeping it on 68 these days, as it's downstairs. Quaint little town with good eats, antique shopping, live music & live theatre on weekends! Small BBQ grill. Laundry service available for a week or more stays.

The Knotted Oak Cottage- Fenced & Dog Friendly

Enjoy this cozy “dog friendly” 2 BR cottage on a quiet residential street in the heart of Monticello’s historic district. This cottage is an easy walk to downtown and is ideal for couples or friends for a relaxed getaway. Well-behaved potty trained dogs ( max 2) are welcome! The cottage has a fenced in yard and is located on a perfect street for dog walking. The cottage front porch is the perfect place to unwind with a cocktail before walking to dinner. On Instagram too!

Fern Hollow Acres A peaceful retreat in the woods

Three bedroom lodge style house nestled in the woods in a retreat setting. Forget your worries in this spacious and serene space. Lovely grounds to walk around , enjoying deer, rabbits, owls and the occasional fox Butterfly, bees and bird sanctuary. Just 30 minutes to FSU/FAMU and the Florida Capitol. Twenty minutes to historic Monticello, Fl A short drive to the headwaters of the Wacissa River county park.with kayak and canoe rentals.

Tally Woods Retreat- 7 Acres with a stream!

Bring your own tent, RV and toys! Camp Micco is a privately owned, 7 acre parcel with a .25 acre cleared area for a campsite and/or RV parking. The rest is a wooded area that has a seasonal stream that flows through the center of the property. Only 28 minutes from the center of Tallahassee which includes a tranquil drive on Canopy Rd. Tent is not included. Unpaved roads leading up to property. There is no house on this property.

Sweet Southern Stay - pet friendly, fenced yard

Relax with the whole family! Located just 5 minutes from the interstate and 15 minutes from Tallahassee, this cozy home offers a perfect getaway from the hustle and bustle. Enjoy a serene setting with amenities that blend comfort with nature. Explore local attractions, historic downtown Monticello, or simply relax on the porch and enjoy the view. Book your stay now to experience the warmth and charm of this hidden gem!

Bogetti Family Farm

Relax with the whole family at this peaceful farm. Enjoy a rest on the front porch or go for a hike around and explore the trails. Schedule an in house massage. Say hello to the friendly goats. Enjoy a day trip to the Gulf or one of the many blue springs of North Florida. 23 miles to Keaton beach, 5 miles to Walmart/Winn-Dixie, and 4 miles to shopping in historic downtown Perry. Plenty of room to park your boat

Private 2 Bedroom Bungalow in Monticello FL

Relax. Take a breath of fresh air and enjoy this beautifully restored 1950's Florida Bungalow in the heart of Historic Monticello, FL! The charming Dogwood House is lovingly furnished to provide a wonderful stay for you and your well behaved/potty trained dogs. Located within walking distance to Monticello's fabulous downtown. Shop, eat, drink, & enjoy! Approximately 30 minutes to Tallahassee or Thomasville.

Smiling Farms Retreat

A unique Two bedroom home, simple, located of 5 A with two ponds on the property. Peaceful, quiet, and nestled around 600 acres of peaceful forest. A small fire pit by the pond and a beautiful 70 foot outdoor covered porch to enjoy the scenery and wildlife. The porch includes a hot tub and an outdoor shower. Forget your worries in this spacious and serene space and just breathe!