Pet-friendly holiday rentals in Jefferson County

Charming 2 Bedroom 2 Bath , Private Cabana

Escape to our cozy, fully furnished 2-bedroom home with queen beds—yours to enjoy in complete privacy! Unwind on the screened porch with stunning views of North Florida’s pastures and rolling hills. Enjoy peace and comfort with private parking and entrance. Fully equipped for your stay, it's the perfect blend of relaxation and adventure. Just 9 miles east of Monticello and close to outdoor fun like hiking, kayaking, and more! Enjoy our lake views , it’s the perfect spot to unwind and recharge!

Private, Hot tub, Adjustable King, Gated Property!

Please read all check-in instructions!! 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.

The Senator Cabin

Historic 19th century cabin updated with all the modern conveniences situated on the 210 acre Jubilee Blueberry Orchards property. Founded by Florida Legend Lawton Chiles, US Senator and Governor. Simply one-of-a-kind with fabulous floors, woodwork, claw tub and handcrafted shower. Breathtaking views all around and the only sounds are wind whispering through long leaf pines and live oaks. Plate glass window overlooking beautiful lake.

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.

Home in Monticello near downtown w/ modern vibes

This entire home has plenty amenities. The 1562 sq ft. corner is home near downtown. The home is cozy, comfortable and functional for humans only. I hope your stay allows you to enjoy your spouse, family, friends or co-workers. Make sure you create lasting memories as you relax, attend college games, graduations, work or just need a nice place to stay. Tallahassee or Thomasville are only a 30-35 minute drive away.

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.