Pet-friendly holiday rentals in Jefferson County

The Longleaf Cabin

Our newest and most modern cabin featuring 3 large bedrooms, sleeping 7 guests with full kitchen and dishwasher, large screened porch with gorgeous forest views and all the comforts of a smart TV, AC, High speed internet and elegant furnishings. Outside the door is a firepit that will tell you many stories and a grill overlooking the lake that features the sunset viewing dock. The Longleaf has premium furnishings and is completely stocked with every necessity for your kitchen, bedroom and bath.

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!

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!

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!

The Budd Pafford Wyche House

The Budd-Pafford House, is nestled in the city of Monticello, Fl. Located 30 minutes east of Tallahassee, Fl. Home of the Florida State Seminoles and the Florida A&M Rattlers. The Budd-Pafford House was originally built in 1833, and is Monticello's oldest home. The property is situated on one acre of lush gardens, exotic plants and trees. You can spend hours identifying the different colors and types of Camellias that Bloom from October thru March.

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.

Country Retreat with a pool

Relax with the whole family at this peaceful place to stay. Nestled 30 mins outside of Tallahassee and 10 mins away from charming Monticello, this home is the perfect retreat for the summer. Enjoy the pool and outdoor sitting space. Gather the family around at night in the huge living room. Is the internet lightening quick? No. Is cell reception blazing fast? No. But, is it quiet and cozy and the perfect place to recharge. Absolutely!

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.

Private Hot tub, Adjusting Kingbed, Gated Property

Please read all! Walking distance from Historic District that's famous for Ghost tours, Good Eats, Antique shopping, Live theatre & Music on weekends! BE SURE TO ADD PET & Any Guest with you UPON Booking! (list service animals as guest). [Smoking Outside Only - medical as well!!!] Pet Fees are per stay - Reduced for returning guests - send booking inquiry 1st to get 50% discount; also given to 1 night booker with 1 pet.

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