Vacation rentals with outdoor seating in Jefferson County

Find and book unique outdoor seating rentals on Airbnb

Top-rated outdoor seating rentals in Jefferson County

Guests agree: these outdoor seating rentals are highly rated for location, cleanliness, and more.

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Guest favorite

A modern green exterior home is presented, featuring a symmetrical facade with large windows and a central front door. Neatly manicured landscaping includes shrubs and flower beds, all set against a backdrop of tall pine trees under a clear blue sky.

Home in Monticello

4.96 out of 5 average rating, 28 reviews

Walk to historic Monticello from this new home!

Newer home in historic Monticello! Fast and reliable wifi. Large master suite with private bath. Fully stocked kitchen with seating for 9. 58 in Smart TV. The outdoor screened in patio is a perfect spot to read a book. Very peaceful place to relax! A beautiful 25 mile drive to Tallahassee. Or take a walk and visit all the shops in Monticello. Great place to walk and ride bikes. Wacissa Springs is 19 miles and is a great place to enjoy time on a kayak. 23 miles to Thomasville. Clean & quiet!

Guest favorite

The entrance features a charming pathway lined with carefully arranged stones, leading to a welcoming porch adorned with white wooden doors. Lush greenery and shrubs frame the space, providing a serene atmosphere, while the screened-in porch invites relaxation under the surrounding trees.

Cottage in Monticello

4.94 out of 5 average rating, 132 reviews

The Cottage at Grand Oaks Plantation

The Cottage on Grand Oaks Plantation is a hidden gem in the small town of Monticello, FL. Nestled under a canopy of 200 year old Live Oaks, you will enjoy relaxing as you watch the horses, ring-tailed lemurs, kangaroos... This restored plantation cottage housed guests in the early 1900's, and is now completely renovated with antique stained glass windows and doors, beadboard walls and a screened wrap around porch. Pool table and darts also. This cottage was featured in Country Living Magazine.

Top guest favorite

A serene river landscape is captured, with tall trees lining the banks. The still water reflects the lush greenery above, creating a mirror-like effect. A clear blue sky is visible above, dotted with soft white clouds.

Place to stay in Taylor County

4.98 out of 5 average rating, 175 reviews

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.

Guest favorite

A spa is featured beneath a wooden deck, with water swirling actively. Soft lighting adorns the overhead structure, and a flight of wooden stairs is visible in the background. Lush greenery surrounds the area, enhancing the serene atmosphere.

Guesthouse in Monticello

4.93 out of 5 average rating, 54 reviews

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.

Guest favorite

A charming cottage is presented, featuring a covered front porch and multiple windows that allow natural light to fill the interior. Lush greenery surrounds the home, enhancing its inviting appearance. Spanish moss drapes from nearby trees, adding to the serene atmosphere of the property.

Cottage in Monticello

4.89 out of 5 average rating, 128 reviews

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!

Top guest favorite

The exterior of a charming two-bedroom home features a light blue façade with white accents. A covered entryway provides shelter, while a stone pathway leads to the porch. Lush green grass surrounds the house, complemented by landscaping and a tree offering shade.

Home in Monticello

5 out of 5 average rating, 12 reviews

Welcome to The Schoolhouse

This special place is close to everything, making it easy to plan your visit. Discover this fully renovated 1926 two-bedroom gem in the heart of Monticello, Florida. Named for one of two schoolhouses originally associated with the church now housing Monticello’s Chamber of Commerce, the home still reflects its history. From reclaimed hardwood floors to refurbished original windows, doors, and moldings, you can experience the best of modern amenities and historic charm.

Guest favorite

A spacious bedroom features a large bed with an orange-brown comforter and decorative pillows. A crib is positioned nearby. Two bedside lamps provide lighting, and natural light enters through windows adorned with blue curtains. Rustic decor includes mounted antlers and a wooden sign above the bed.

Home in Perry

4.97 out of 5 average rating, 31 reviews

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!

Top guest favorite

A spacious living area features large sliding glass doors that open to a wooden deck overlooking the surrounding woods. Natural light illuminates the room, which includes a comfortable seating arrangement and side tables. A ceiling fan and wall-mounted television are also present.

Cabin in Monticello

4.97 out of 5 average rating, 92 reviews

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.

Guest favorite

A rustic wooden cabin is nestled beneath a large oak tree draped in Spanish moss. The porch, equipped with seating, overlooks a spacious lawn surrounded by tall trees. Natural light reflects off the cabin's surfaces, highlighting its inviting entrance.

Farm stay in Perry

4.85 out of 5 average rating, 40 reviews

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

Superhost

A spacious living area features a black leather sofa, complemented by a coffee table and a stylish lamp. Exposed wooden beams and walls create a warm atmosphere. A ceiling fan hangs above, providing a sense of openness. Natural light streams through a nearby window adorned with fabric.

Cabin in Monticello

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.

Guest favorite

The charming bungalow features a welcoming front porch with white railings, surrounded by a well-maintained lawn. Mature trees offer shade, and the home's warm exterior blends harmoniously with the lush, green landscape.

Home in Monticello

5 out of 5 average rating, 63 reviews

Dogwood House; Private 2 Bedroom in Monticello, FL

Charming 1950s Florida Bungalow in Historic Monticello Florida Stay at The Dogwood House—a beautifully restored bungalow just steps from downtown shops, dining, and drinks. Pet-friendly for well-behaved pups, this cozy retreat is the perfect mix of comfort and charm. Only 30 minutes to Tallahassee or Thomasville!

Guest favorite

A welcoming entrance is framed by lush greenery, with a light blue exterior and a pink front door. The porch area is partially covered, featuring a textured stone pathway leading to the door.

Home in Monticello

4.96 out of 5 average rating, 75 reviews

The Pearl Cottage - kid and pet friendly!

Relax with the whole family, well behaved dogs and cats included! The Pearl Cottage is located on a peaceful and charming street in downtown Monticello. A park with a playground is only a couple blocks away. Eat and shop local for the day. Tallahassee is 30 minutes away, Alligator Point is 1hr 20 minutes.