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!.

Hummingbird Haus | 2 Unit | 9 Beds | 6 BR | 3.5 BA

Welcome to Hummingbird Haus, a charming 3200 sqft, 6-bedroom, 3.5-bath home featuring 2 expansive decks— one of which incorporates a large tree, creating a cozy, treehouse-like atmosphere. This elevated home is situated on a cul-de-sac in a scenic neighborhood, close to FSU and Downtown. Enjoy being close to it all while having a peaceful retreat to unwind. The layout includes a spacious 4-bedroom, 2.5-bath main home on the upper level, along with a 2-bedroom, 1-bath suite on the lower level.

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.

Twisted Pine Lake Cabin, secluded & near town

Close to everything, a million miles away....... Down the two-track driveway, past the view of the nearest neighbors, our new custom cabin awaits. Rest easy on the screened porch, 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.

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.

Midtown*Pool*Walk to Dining*2 miles to FSU/Capitol

Steps from all that Midtown has to offer, Midtown Retreat’s private POOL & deck is an oasis to enjoy it all from! Our light-filled midcentury charmer is spacious/cozy. Only 2 miles to Capitol & FSU, this home is a treat to stay! 3 miles to Doak Campbell Stadium makes for a quick trip for FSU games. Ideal spot for FSU visits, Capitol business trips & Midtown nightlife! Heart of Tallahassee! ✅Pool ✅Wi-Fi ✅Pet-friendly ✅Work-from-home space ✅Free Parking ✅Walk to Midtown’s best dining/bars

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.

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!

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.

Modern 4BR Retreat w/ Private Pool | Sleeps 12

Whether you're in town for an FSU or FAMU event, graduation, family getaway, or business trip, this renovated 4-bedroom home is the perfect home base. Relax by the private pool, unwind in the spacious indoor and outdoor living areas, and enjoy accommodations for up to 12 guests. Just minutes from FSU, downtown Tallahassee, the Capitol, and top local attractions, this home has everything you need for a memorable stay.

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.