Holiday rentals with outdoor seating in Thomasville

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.

The Jewel of Thomasville - Sleeps 10 + game room!

Relax with the whole family at this charming farmhouse in the heart of Thomasville, GA. The house was lovingly remodeled with modern details to provide a luxurious yet charming feel. Located on over a half acre in a highly sought after neighborhood, you can unwind into the beautifully decorated and well equipped home, or retreat to the private patio or game room. Although shops and top restaurants are only a 3-5 minute drive away, the area feels peaceful and secluded.

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!

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.

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 FSU/Bragg/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!

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!

Wimsam Carriage House

Enjoy the South Georgia pines and magnolias in this well-stocked, comfortable, & family-friendly carriage house. Just minutes from Thomasville's historic downtown district, this apartment features an open floor plan, nine acres of wooded trails, ample yard space, and gated entry.