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!

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.

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.

Lagniappe, Get a little extra!

Our property is conveniently situated within walking distance of the local grocery store and other charming shops. You'll have everything you need at your fingertips. During your stay, take advantage of the washer and dryer, making laundry a breeze. Come and experience the rich history and warmth of Monticello from the comfort of our delightful Airbnb. We can't wait to host you and ensure a memorable stay. Book now and start counting down the days to your unforgettable getaway!

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.

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!

Charming Perry Home ~ 2 Mi to the Gulf!

Rest and relax in this sweet, secluded vacation rental just minutes away from the Gulf of Mexico! This 4-bedroom, 2-bathroom home is the perfect space to host your next vacation. If adventure is calling, this house puts you close to not only the ocean, but trails, museums, downtown, and more. Here you can take some time out in the boat, catch your dinner, utilize the cleaning station, grill out in the backyard, and enjoy a beverage from the tropical bar.

Spring Warrior Pines

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!

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.

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.