Family-friendly vacation rentals in Thomasville

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!

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.

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.

Little White House in Downtown Thomasville

Situated in one of Thomasville’s best historic districts, this home was originally located on WWII Thomasville Army Air Base and was brought to its current location in the late 1940s. It is freshly renovated and has everything you need to enjoy your stay in town. The neighborhood is quiet and safe. Best of all, it is an easy walk to the downtown area, featuring boutique shopping and many wonderful restaurants. Only 3 blocks (0.3 miles) to the bricks on Broad Street. Cold AC!

Southern Charm (Kid’s Bunk Room)

Welcome to "Southern Charm"! A charming home featuring 3 bedrooms/2 bathrooms with plenty of room for all. Two beds feature queen mattresses and the 3rd is a “woodlands” themed bunk bed room perfect for children complete with toys/games/puzzles to play with. We hope you enjoy your stay! *Your specific dates not showing? We also own the Quail Cottage too. We will try to accommodate you as best as we can. Just send us a message & read our great reviews!*

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.

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.

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

Southland Cottage - Walk to Historic Downtown

Discover Southern charm in our cozy cottage, nestled in the heart of the Love Street historic district, just blocks from downtown Thomasville. Perfect for a getaway, our retreat offers modern amenities and a peaceful atmosphere. Experience the South's timeless allure and hospitality during your stay with us. We look forward to hosting you!

Spacious home - all bedrooms have a private bath

Spacious home with room for the whole family! Peace and serenity await in this tranquil property that sits on over 1 acre in the charming town of Thomasville. Each of the three bedrooms has its own private bath. This fully equipped and professionally decorated home is ready for a relaxing and comfortable getaway.

Big Oak Cottage

My place is a 10 minute walk to parks, restaurants and the historical and Southern Living recognized, downtown area. You’ll love my place because of the back yard, the comfy bed, and the coziness. My place is good for couples, solo adventurers, business travelers, families (with kids), and furry friends (pets).

Victoria Cottage -Walkable to Downtown

Feel right at home in this masterly crafted new cottage. All the ambiance you would expect in a historic neighborhood, but with all the amenities of modern comfort. Thomasville is a unique destination, appealing to those seeking to experience southern historic downtown living.