Holiday rentals in Leon County

Charming Charley - Cozy and Comfy near Everything

Welcome to "Charming Charley" where simplicity and southern charm flourish in this cute townhouse suited for up to four. We are nestled and conveniently located near EVERYTHING. Just minutes from the colleges or a 5-minute drive to the hottest nightlife, restaurants, and shops in the city. We specialize in affordable elegance and are committed to providing you with a complete and accurate depiction of your modest vacation rental home. Any questions...just ask, that is what we are here for.

Beautiful Guest House in Desirable Northside

Hello and welcome to our home! This guest house is in our backyard and is very cozy with a large, screened-in porch. Sit in a rocking chair on the porch and enjoy the sounds of the many birds and the company of butterflies and hummingbirds. The King size bed is so comfortable! Our neighborhood lies between the Market District to the south and Bannerman Crossing to the North. There is shopping as well as many restaurants all around us. Downtown and FSU are 20 min away depending on traffic.

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.

Private Garden Retreat | King Bed | TMH + Downtown

Welcome to your peaceful getaway, central to everything in Tallahassee! King bed ✔ Spacious patio with an original mural and fenced back yard ✔ Private Parking ✔ Dogs Welcome ✔ Well stocked kitchenette ✔ Mid-century charm ✔ Coffee, tea, snacks ✔ Cozy up with a movie in front of the custom wood slat wall, cook dinner with a well-stocked kitchenette, and get a quiet night's rest under a stylish wood ceiling. You are: - 5 mins from TMH - 8 mins to downtown - 8 mins to FSU - 7 mins from I-10

Studio walking distance to Stadium & Nightlife!

Industrial Modern Studio in the heart of Tallahassee, Walking distance to Doak Campbell Stadium, Madison social, and all college town restaurants and nightlife. This is the perfect stay for game days or to visit FSU which is a 5 minute walk to campus. Bring your bicycles and your a 10 minute bike ride to the Railroad square arts district, Cascades Park and all government buildings in downtown. You could not ask for a better location in Tallahassee Florida. Extremely comfortable king bed.

1940’s Midtown Beard St. Charmer

Located in the heart of midtown within walking distance to many delicious restaurants and local shops, this space is hard to beat. Private entrance, private (unshared) space, small studio apartment with queen sized mattress. Kitchen has fridge, microwave, oven, dishwasher. Smart TV, Wifi, off street parking (1 assigned space), situated in an adorable neighborhood full of Tallahassee charm and history. Fits 1 person perfectly or up to 2 max. Non-Smoking unit! Pets accepted with fee.

Woodsy Loft near I-10

A short 2 mile drive from I-10 for those traveling you can unwind at this garage-loft with private entrance surrounded by trees with a backyard oasis. ✨ Step inside to a modern main room with canopy bed and well-equipped kitchen. Find your haven in comfy bedrooms and soak up the sunshine on the expansive deck☀️ Splash in the sparkling pool, have water gun fights in the yard and have dinner in the poolside pergola! Minutes from downtown, museums, and natural attractions.

King Bed- 10 Guests- Dogs-fenced yrd-deck

Spacious, stylish, and packed with comfort—your perfect NE Tallahassee escape! This 2,000 sq. ft. home features 5 comfy beds, a queen pull-out sofa, and Smart TVs in every room. The fully stocked open kitchen makes dining a breeze, while the fenced yard, deck, and fire pit create the perfect outdoor hangout (pets welcome!). Located in a peaceful neighborhood just minutes from top shopping and dining, plus a 2-car garage with remote for easy indoor parking.

Convenient Cottage | Midtown TLH

Welcome to our charming, cozy cottage in Tallahassee's Midtown, less than ten minutes from Doak Campbell Stadium, the Florida State Capitol, Cascades Park, and the city's best restaurants. This is the perfect two queen bedroom stay for game day, concerts, graduation, and more. Make yourself at home with WiFi, live YouTube TV, full kitchen with Keurig coffee maker, washer/dryer, back deck, and free off-street parking.