Family-friendly holiday rentals in Leon County

Luxury Haven w/ Many Amenities

I live in NJ close to my parents, and my sister lives in Tallahassee. To make it easier for my parents (who are separated) to see my sister and their grandchildren, I surprised them with the keys to a "his and her" condo in the same complex. You won't find an Airbnb in the area with more abundant amenities because I wanted to give my parents the home away from home they have always dreamed of. If the listing is available, my family isn't in town, and so this beautiful condo is available to use!

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.

Live Oak Cottages III. InTown - 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.

Guesthouse - Studio in the woods

The guesthouse sits tucked back in the woods next door to our home, offering privacy and quiet once you arrive. The surrounding area is rural and unpolished - but the property itself is clean, peaceful, and thoughtfully maintained. Check-in is between 3:00 pm and 11:00 pm EST. We do not allow check-ins after 11:00 pm. This property is not suitable for anyone with mobility issues or who is unsteady on their feet. No smoking, e-cigs, or vaping permitted in the cottage or on the property.

Twisted Pine Lake Cottage, secluded & near town

Close to everything, a million miles away....... Down the two-track driveway, past the view of the nearest neighbors, our three-bedroom cottage awaits. Rest easy on the patio, with its view of the two-acre lake or cross the adjacent foot bridge to the island. Fish for bass and bream, stroll the walking path, paddle around and enjoy the wildlife, or just relax far from the madding crowd. This slice of paradise sits on 12 acres; our home is across the lake, out of sight and out of mind.

The Carriage House

Our lovely French inspired guest house features an open floor plan, 12-foot ceilings with real wood beams, a fully equipped kitchen and large brick patio overlooking a spacious backyard with shared pool. The two bedrooms are connected by a jack and jill bathroom featuring a tub/shower combination. the second bathroom, located just down the hall, has a standup shower. For additional guests, there are more sleeping arrangements in the family room on a single bed pullout love seat.

Magnolia Manor Estate with Heated Indoor Pool

Retreat to in-town country living with massive, picture perfect live oaks and abundant wildlife. Your family and friends will enter this home in awe of its unique qualities including the incorporation of the beautiful natural environment through expansive windows in every room and an indoor pool. This is a peaceful sanctuary for you and your family and friends to enjoy a wedding weekend, Tallahassee visit, FSU/FAMU gameday, reunion, and other activities. We have a generator.

Home away from home Northside charmer suite

Lovely and completely renovated 1100 sqft in-law suite, fully self contained and private. It comes complete with a fully equipped kitchen (no commercial food preparation allowed) and bathroom with walk-in shower. Queen size bed in the bedroom, with a Queen size sleeper sofa in the living room. Has its own private entrances and dedicated driveway parking area, as well as self-check-in. No pets allowed. This is a strict non-smoking space, no smoking is allowed on the property.

My House, Your House

This home away from home is the perfect place to lay your head after a long day from traveling. Whether you're here for homecoming or traveling for work, our home is nestled in a quiet community a short drive from local restaurants, shops, hospitals and the local Universities. The space includes 3 fully furnished bedrooms, coffees and teas. We also provide everything you need to cook and serve a meal. Access to washer and dryer. We are local and available if needed!

Midtown | FSU 2.4 miles | Capitol 1 mile

MIDTOWN CAROLINA CORNER (est. 1927) sits in the heart of Florida’s capital city in a desirable location for safety & convenience! Completely renovated with a coastal vibe featuring 9 ft ceilings, transom windows, roomy bedrooms, & heart pine flooring! The large kitchen has beautiful brick flooring, dining room, indoor and outdoor porches perfect for entertaining! The historic neighborhood is great for evening strolls, and convenient to rooftop bars and parks.

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.

Walk to Museum | Near FSU | EVSE

* Lake Water severely is low, Tallahassee is in a drought* ✈️ 5 minutes from Tallahassee Airport! 🏟️ 12 minutes from Capitol, FSU, FAMU and TCC 🤪 No crazy check out instructions! 🐕 Pet friendly! 🛶 Kayaks available! 🔋Remote control bed! 🌺Nature trails! ⛵️Private Lake access! 👩‍💻Traveling work friendly! 🎣Fish off the dock! 🔑 Remote and keyless entry. ⛳️ Golf course 10 minutes away! 🚿 Walk in shower and separate tub! 🎸 Piano, guitar, and board g