Holiday rentals in Monticello

4.96 out of 5 average rating, 27 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!

Place to stay in Taylor County

4.98 out of 5 average rating, 162 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 comfy twin mattress bed . 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. Fiber Optic Wi-Fi. The cottage is fully furnished, mini frig, microwave, toaster, coffee pot, dishware, bed and bath linens & basic cooking condiments.

4.94 out of 5 average rating, 131 reviews

Cottage in Monticello

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.

4.95 out of 5 average rating, 187 reviews

Cabin in Tallahassee

Coastal City Cabin: A Cute Florida Getaway A-Frame

Picture this.. Spend the day fishing out on the coast or swimming in the world's largest freshwater spring then some fun in town with great eats & live music! Finish the night with a hot tub soak under the stars. No worries, you can do it all again tomorrow! Conveniently nestled between Tallahassee and the 'Forgotten Coast', our cabin is a perfect match for your adventure-filled vacation. A quick 15 minute ride from the Tallahassee airport has you enjoying the sunset from our rocking chairs.

4.95 out of 5 average rating, 124 reviews

Home in Thomasville

Edgewood Cottage

Whether you're in town for an event or looking for a getaway, you'll feel cozy, comfortable, and right at home in this historic cottage. Built in 1916, the home offers historic charm and modern amenities. With more than 1,600 sq. ft. and three bedrooms, there's room for the whole family! There's a huge fenced-in yard and Macintyre Park is just half a block away. The front porch and back deck offer serenity under the pines. Or take a 3 minute drive to experience all that downtown has to offer.

Superhost

Guest house in Monticello

4.91 out of 5 average rating, 35 reviews

Guest house, Hot tub & King Bed on Gated Property!

Please read all check-in notes! 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.

4.89 out of 5 average rating, 128 reviews

Cottage in Monticello

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!

4.97 out of 5 average rating, 455 reviews

Cottage in Thomasville

The Shed-King Bed-Boho - Cabin- Grand Piano- WiFi

The Shed is located in a sprinkle of country, splash of city, Thomasville, GA. The Shed hosts a king bed and a combined kitchen living room space with a pullout Queen couch. You can spend your evenings outside on the patio with a fire or explore the beauty of historic downtown only 5 minutes away! A private 2 room guest house with a unique modern flare. No contact, keyless entry on arrival and a cozy, safe, clean space for your get away! We look forward to hosting you!

4.97 out of 5 average rating, 89 reviews

Cabin in Monticello

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 suite in Tallahassee

4.97 out of 5 average rating, 686 reviews

Private/Entire Studio, Private Keyless Entry

"Private Entrance" 2nd-story STUDIO w/lots of windows. Wood floors, central AC/heat, 1/2 bath, queen bed with new mattress, fridge, Krueig, microwave, WIFI, TV, closet space, ROBES FOR PRIVATE OUTDOOR HEATED SHOWER and towels. Established neighborhood less than 2 miles from FSU and downtown; 1 block to Tallahassee Memorial Hospital. Restaurants under 1/2 mile! It is on our property and we personally clean the studio. Go Noles!

5 out of 5 average rating, 143 reviews

Home in Tallahassee

Sienna Lee Gardens: A Beautifully Renovated Home

Relax and unwind in this beautifully renovated 4 bedroom/3 bath home nestled on 20 acres of picture perfect live oaks, organic blueberry orchard, and abundant wildlife. There are so many places for entertaining including a large heated swimming pool (heated from March-Nov). There's a fully equipped kitchen, luxury beds and hotel quality linens. Every room has cable TV and internet throughout the house.

4.95 out of 5 average rating, 64 reviews

Charming cottage located on a historic street.

The Camelia Cottage is located on charming Pearl Street, surrounded by historic antebellum homes. Enjoy quiet evenings in this unique neighborhood. Camelia Cottage is within 30 minutes of Tallahassee and within walking distance of quaint shops and restaurants. You will certainly enjoy the small town atmosphere. Camelia Cottage has recently been updated, there are two beds one king and one full bed.

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Other great holiday rentals in Monticello

5 out of 5 average rating, 6 reviews

2-bedroom gem in Monticello.

DanielRating, 5 stars2 weeks ago

Was very impressed with this stay it was perfect for me and brother to stay in while we visited family for the weekend. Very peaceful and private stay. Very nice interior design and amenities and it’s bigger than it looks! Not far from I-10 or Monticello. Can’t wait to be back.

5 out of 5 average rating, 6 reviews

Home in Thomasville

Charber Farm Cabin

LisaRating, 5 stars3 weeks ago

We had a wonderful stay here at this sweet cabin. It was so peaceful and surrounded by nature and sweet farm animals... We even experienced the nostalgic sound of a train going by a couple times during our stay...so charming. The cabin was just as described but better. The attention to detail in the furnishings was wonderful and it was apparent that the host Christeenia , made all efforts to ensure your stay was all that it could be, including providing all kinds of perks for your pet (doggie bone snacks, doggie waste bags etc). The beds were very comfortable and we even enjoyed cooking a few meals at home with all the stylish and health conscious cookware and utensils and bar ware provided. Everything you needed was there. The host was very responsive and offered much information on all the favorite shops and restaurants in Thomasville. It was only a few minutes drive from downtown Thomasville and provided the tranquil environment we were looking for. Great stay

5 out of 5 average rating, 10 reviews

Villa in Monticello

The Bungalow

NathanRating, 5 stars1 month ago

Quiet and clean spot near a pizza and ice cream shop. The host was very responsive and always available. You have to pull into a gravel driveway and between two buildings to get to the parking area with the businesses and rental unit. Nice spot in Monticello.

Private room in Tallahassee

4.95 out of 5 average rating, 225 reviews

Eclectic Midtown Room/bath by WholeFoods near I-10

SarahRating, 5 stars3 days ago

Philip hosted my father and my father said: “Philip is great. He is vegetarian and is quite into gardening. He’s a very interesting man. We talked for about an hour. Everything inside is clean. He has two houses, each with three rooms he rents out. Renters have full house privileges and Phillip keeps a lot of food for everyone.” Would stay again! Thank you, Philip!

4.84 out of 5 average rating, 19 reviews

Sunset Blue House - Secluded Pool Home on 4+ acres

MatlethaRating, 5 stars2 months ago

The house was clean and spacious. The pool and yard was pristine. The host gave clear instructions and, whenever we needed anything additional, she was incredibly friendly, responsive and helpful. Our guests enjoyed their stay and we will definitely recommend to others.

Guest house in Monticello

4.96 out of 5 average rating, 50 reviews

Cozy Country Cottage near Tallahassee

JessicaRating, 5 stars3 months ago

Tom - your home is exceptional. My husband, his father, and a friend traveled down to fish in the lake nearby. Your air bnb was the absolutely perfect spot to park the boat, be close to the lake, and enjoy a peaceful guy’s weekend fishing and relaxing. My husband said the home was absolutely pristine condition. He was extremely impressed with how thoughtful you were in your amenities (shampoo / conditioner/ toothbrushes - everything you could possibly need was available!). Your cleaning fee is extremely reasonable with simple checkout instructions. We are already discussing when we could come down to stay again. Thank you for providing a wonderful space! Highly recommend staying here. You will NOT be disappointed.

Guest house in Monticello

5 out of 5 average rating, 17 reviews

2 Bedroom/2 Bath Cottage close to Tallahassee

ChristopherRating, 5 stars1 month ago

Absolutely beautiful high end guest house on an amazing property with beautiful healthy horses visible in their stables. This is a beautiful serene place with lots of trees, land and fresh air. If you like horses, farms, country, this guest house is for you! Very clean and modern amenities with an old Southern charm. Lovely property, will definitely be back! 5 stars 🌟