Holiday rentals with outdoor seating in Leon County

Live Oak Cottages II InTown-Nature Retreat

Private long driveway to a quiet setting. Beautiful Live Oak trees around the grounds. It’s the upstairs cottage apartment with tall windows giving you a view to the Live Oak trees canopying together. The one by the cottage is 200 +years old!! Charming and cozy place to relax or work! Living room windows are tinted for privacy. Comfy bed and all the bedding is cleaned in between guests. There are plenty of towels, linens, and the essentials you need to be comfortable. Smart tv and Wifi too

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!

3 Bedroom Trendy Elegant Vibe close to Colleges

Relax in this calm, stylish space! Enjoy this oasis in Florida's capital. Recently renovated, this home is close to downtown, FSU, and FAMU. Wake up in this bright modern smoke-free and pet-free home. You get the entire place with no space shared. This home comes equipped with 2 queen size beds, a set of twin beds, and Smart TV's in each room with your favorite apps! Free Netflix, DIsney, Hulu and ESPN+ The home comes with a nice sized screened in porch and large back yard. We are kid friendly.

Cozy Country Cottage - Waterfront!

Enjoy the sounds of nature when you stay in this unique country cottage on private Turkey Pond. Deer, turkey & raptors are just some of the wildlife you may encounter. Stunning sunsets are common & kayaks are on hand for a paddle. There is outdoor seating & a sun umbrella for the porch and stars twinkle on clear nights. Special touches make your stay comfy & cozy including on-demand hot water, a luxurious queen bed w/ a cozy comforter, mini-split heat/ac, dish network, smart tv & much more.

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.

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.

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.

Private Garden Retreat, King Bed, TMH, Downtown

Welcome to your peaceful getaway, central to everything in Tallahassee! King bed ✔ Spacious, mural wall patio with a 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 in the 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

Shangri-La Treehouse

Shangri-La Treehouse is the 1st and only luxury treehouse in Tallahassee, Florida's Capital City. Nestled between ancient oaks, Shangri-La Treehouse is luxury in the wild where serenity is found. You are invited to enjoy 9.5 acres of verdant land amidst ducks, deer, owls, and other assorted wildlife that call Shangri-La home. A thoughtful, adults only (21+) romantic getaway for 2 that can accommodate up to 4 guests comfortably.

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.