Pet-friendly holiday rentals in Jefferson County

Private updated Cottage, Cozy and Spacious

Escape to this charming, private 1-bedroom cottage with a queen bed and spacious living area—perfect for two! Enjoy stunning lake and orchard views from your cozy retreat, complete with a private picket fence, entrance, and patio area for outdoor relaxation. Fully equipped with all the comforts you need for ultimate peace and quiet. Just 9 miles east of Monticello, 20 minutes from Thomasville, and 35 minutes to Tallahassee. Unplug, unwind, and make unforgettable memories in this nature haven!

Little Fish House (Casita de Peces)

Come stay at this unique tranquil getaway in our fully renovated guest house located on our beautiful rural Florida farm. This is 'old Florida' at it's best; peace, quiet, gorgeous views, wildlife, and the conveniences of home. Located two miles from the Gulf and 10 minutes from Keaton Beach; some of the last undeveloped natural areas of coastline in Florida known for birdwatching, world-class fishing and fantastic summer scalloping. Gated private property, plenty of paved parking for a boat.

Peaceful 1BR on 1.25 Acres

Unwind in this cozy 1-bedroom home nestled in the quiet countryside of Lloyd, Florida—20 minutes from Tallahassee and minutes from I-10. A peaceful retreat on 1.25 acres features a west-facing screened-in porch perfect for enjoying your morning coffee or glowing sunsets with a glass of wine. The space is curated with new and antique furnishings and original artwork. A fully equipped kitchen is perfect for guests who love to cook. A laundry room and home office work area completes the space.

River Front Cottage Aucilla River, Taylor County

Furnished cottage with river view windows and a walk around deck. Open floor plan with king size bed and choice of either the full-size sleeper sofa or (2)comfy twin mattress beds . Enjoy relaxing and watch the river flow by from the swivel rocker recliner. Newly installed AC/Heating unit. Wall mounted swivel TV for easy viewing 200 channel Dish TV. Wi-Fi. The cottage is fully furnished, mini frig, microwave, toaster, coffee pot, dishware, bed and bath linens & basic cooking condiments.

Private Hot tub, Adjusting Kingbed, 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.

Spring Warrior Pines

We accept extra registered guests. Plenty of land for boats and vehicles. Use the cleaning station for all your hunting and fishing trips. A fire pit to enjoy the night air. Swings for the kids & for the adult kids is corn hole, checkers & horseshoe games. Furry friends are welcome and have their own suite, if needed. (fee is $30 per pet)The perimeter is fenced. We have a Baby crib and Highchair for our littlest friends. Gas and charcoal grill is available, bring the charcoal!

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.

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

Wee Bairn (little one in Scottish) Not Available

Brand new - completely renovated inside for a unique setting. A National Historic Register carriage house/barn from 1862. It has a furnished kitchen, living space and a sleeping loft. Full bath with shower, wi-fi, satellite tv with Netflix. Located in wooded area very near main house. Breakfast is included in the main house. Sleeps up to four persons comfortably.