Family-friendly holiday rentals in Leon County

Luxury Living w/ Abundant 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!.

Like New Midtown Retreat | 3 TVs • Ethernet Port

This is a newly renovated 2BR 1 Bath apartment on the first floor located central off Meridian, a Canopy Road, in Tallahassee, just a short ride or walk to shopping, Whole Foods, Riccardos, ABC, Publix, Walmart, Food Glorious Food, Winthrop Park, Planet Fitness and hundreds of nearby restaurants and coffee shops, Near John Knox and the Trousdell Aquatics Center. These units come with over the top line beds, 3 Tv's and fast internet-20 minutes to just about anywhere in Tallahassee. Pool 0.9 mi.

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.

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.

The Nene Nest

Cozy & comfortable, Nene Nest is located in a quaint neighborhood right in Downtown Tallahassee. Tucked away from the hustle & bustle of city life, this home is the perfect, peaceful getaway with quick access to Tallahassee's finest restaurants, shopping, and of course, the Florida State Seminoles! One mile from Cascades Park, and under 3 miles from Doak Campbell Stadium, this residence is where you want to be. Large bedrooms with an oversized back yard, perfect for family, friends, and dogs!

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.

Eclectic Midtown home by Whole Foods near I-10

An eclectic home away from home. Diverse ideas and style from a broad range of sources and millennia. If you thrive on creativity, diversity and a bit of thought provoking conversation , you may love this house. This is not the Holiday Inn. Expect the unexpected. Located in a quiet neighborhood and the middle of town. The house has been remodeled and I am working on a carport with a solar panel roof. There is some construction happening outside though not while guests are present.

Modern & Cozy ~ Mins to Dwntwn & FSU ~ Gym ~ Yard

Step into the spacious and comfy 2BR 2Bath home nestled in a tranquil and picturesque Indian Head neighborhood just a stone's throw away from the vibrant downtown. It offers a relaxing retreat close to many restaurants, shops, and exciting attractions. Relax and enjoy the modern design and rich amenity list... ✔ 2 Comfortable Bedrooms ✔ Fitness Room (can be used as a 3rd bedroom) ✔ Fully Equipped Kitchen ✔ Back Porch & Yard ✔ Workspace ✔ Smart TVs ✔ High-Speed Wi-Fi See more below!

THE SPACE at Magnolia Hill

We love the wooded setting of this mid century cottage (circa 1955) located in a quiet downtown neighborhood. Enjoy the totally remodeled kitchen with new appliances as well as the original gleaming hardwood floors. At over a 1,000 sq. ft, THE SPACE @Magnolia Hill is the perfect place to Work or Relax or just Recharge! We are conveniently located to downtown, The Capitol complex, FSU and FAMU as well as near great restaurants, shopping, parks and Tallahassee Memorial Hospital!

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.

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!