Holiday houses in Monticello

Cottage 308-Walk to Downtown-Historical-King Bed

Welcome to Cottage 308! This adorable 1863 historical home is loaded with charm! Come enjoy its' towering tall ceilings, arched doorways, and quaint spaces for your perfect get away! Located in peaceful, Victoria Place and within walking distance of the brick streets of downtown Thomasville. This one bedroom, one bath home hosts a king bed, lovely walk in shower, fully furnished kitchen, laundry room and coffee bar! All the charm of this home awaits you to make your stay one of a kind! Welcome!

Private Hot tub, Adjusting Kingbed, Gated Property

Walking distance from Historic district famous for Ghost tours, Good Eats, Antique shopping, Live theatre & Music on wkends! Message any questions! Laundry service available for week or more stays. Planned early check-in/spontaneous late check-out $15 hr. 3 hrs Max. (billed as payment request through app anytime after check-in) Please be sure to add pets to booking! Small BBQ grill & ice cooler; no ice maker. Smoking Outside Only - includes medical! (nico. vape ok) Service dogs are extra guests.

Suite and Simple

Welcome to your centrally-located retreat in Midtown Tallahassee. Being 15 minutes from FSU & FAMU is a perfect distance, and about 5 minutes from TMH & HCA. This neighborhood location is quiet. Experience a peaceful stay at the Suite and Simple, a mother-in-law suite located on the right side of the home. Enjoy the privacy of your own kitchenette, bedroom, bathroom, and private entrance. You can sleep a total of four people comfortably with a couch futon that expands into two twin-sized beds.

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.

Live Oak Cottages III. 2/2 In Town Nature Retreat

A Beautiful private location with the cottage nestled under 100-300 Plus yrs old Live Oak trees. Sits off the street, very private. Comfortable, stylish interior with all that you need. Sparkling clean! Quality linens. W&D.All bedding and throws washed every time. Kitchen supplies, extra towels. Sodas, water, creamer for free. 2 full baths, 3 Tvs and WiFi. It's the right side of a duplex where the wall between is completely soundproof. Close to the Capital,Colleges, restaurants and shopping.

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.

Cozy and Quiet Guest Suite for 2

This peaceful and centrally-located private guest suite has everything you need. Pull into your own driveway with a private entrance to a comfortable room which has an en-suite bathroom, its own air-conditioning, a mini-fridge and a microwave. It's like a hotel room without the noisy neighbors or hassle of check-in. The guest room is attached to a residential home in an established neighborhood that is within four miles of the capital and FSU. It's perfect for 2 guests!

Maple Tree Cottage - close to downtown

Forget your worries in this simple and serene space. Just a short walk and you'll be enjoying all the charm that downtown Thomasville has to offer. Our home welcomes you with 2 bedrooms, each with queen size beds, and 1 bathroom. All of your day-to-day conveniences are available in our home allowing you to settle in like it's yours. The home is located just blocks away from all of the shopping and restaurants on Broad Street.

King Bed-Pets -Quiet-Huge fence Yrd

Unwind in this spacious, equestrian-themed retreat in a peaceful upscale country setting! Set on a large fenced lot, this dog-friendly home offers comfy new beds, Roku TVs in every bedroom, and all the amenities you’d expect. Enjoy shuffleboard, gather outdoors, or relax with easy access thanks to the 2-car garage with remote. Plenty of room to roam and recharge—perfect for a serene getaway just outside the city buzz.

Gardenview Tiny House

Enjoy the sounds of nature when you stay in this unique tiny home in a garden setting. Quiet and private neighborhood. Our Tiny House space is perfect for one guest and cozy for two. We are located about 8 miles (15 to 20 minutes by car) from the Forida Capitol Building and the FSU Campus. We offer a 15% discount for bookings of 7 days or more, and 40% discount for 28 days or more.

Executive Suite on Park Ave.

This is the most elegant and tranquil 1250 Sq ft. of pure comfort! It features a library quiet central smart H & A. system (not a window air) can be set to 70 in the summer and 68 in the winter. Large one bedroom with a Tempur-pedic luxury king size bed . 7 ft glass shower . Sofa can be used as an Extra long twin. Full kitchen with dishwasher

Historic Levy Park! 2 miles to Bragg/FSU/Capital

Welcome to historic Levy Park! We are excited to host you at this beautifully restored Italian inspired getaway. This vibrant neighborhood is one of Tallahassee's oldest and boasts a lovely mixture of old homes and local Tallahassee families. There are homes on our street over 100 years old, and families that have lived here for generations!