Holiday rentals with outdoor seating in Tallahassee

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

COZY Studio Escape CLOSE-IN Kitchen Pool WRK-SPACE

Cozy~Quiet~Close~In Work-Space! FSU!/ Collegetown!, Midtown, Capital, FAMU. EnSuite, Kitchenette, Cottage-feel, New Memory-Foam Queen Panel Bed & Luxurious Oriental. Private Side Entrance. Private Bath & Pool Access. Shadey~Oaks, Lovely Flowers & Birds. Microwave, Huge Toasteroven, Stovetop, Barsink, Granite Counter, Minifridge, Singleserve Coffee Maker, Utensils. Safe~Quiet~Shady Sidewalk 'Walking Neighborhood'. Poolside Patio & Porch w/ Glass Table. We Love Our Dog! No Children Or Animals Plz

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.

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.

King bed-Office-Pet-Fenced Yard-Fast WiFi

Welcome to our charming Bo-ho retreat! This 3-bed, 2-bath dog-friendly house is a Bo-ho lover's dream. Step into a world of relaxation as you immerse yourself in the carefully curated Bohemian Decor. Unwind in the cozy living room or whip up a delicious meal in the fully equipped kitchen. The bedrooms are comfortable and tranquil. Outside, the private and spacious fenced-in yard is perfect for your fur babies to roam freely. Come experience the harmony and beauty of this perfect Bo-ho getaway.

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 games available 🍳Awesome Grill set up!

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.

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.

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.

Cozy Coffee Inn King Bed FSU FAMU TSC Downtown

Enjoy a get away at this conveniently-located clean and modern townhome. Featuring 2 bedrooms: one with a king bed, and one with 2 queen beds. Each bedroom has a Roku smart TV. Eat-in Kitchen boasts a coffee bar and tea selection, dining table for 4 and 3 barstools. Reserved parking for 2 cars. 10 minute walk to Doak Stadium. It is also convenient to Downtown, Convention Center, Eateries, Airport, Collegetown and all campuses. Come Be Our Guest! (NO SMOKING inside)

Historic Briarcliffe Cottage

Experience historic charm and modern comfort in this beautifully restored two-bedroom stone cottage, built in 1939 by a Scottish architect using limestone from nearby Wakulla. Listed on the local historic registry, it features hardwood floors, original art, cozy furnishings, and thoughtful amenities. Nestled in Tallahassee’s Old Town—just one mile from the Capitol and 1.5 miles from FSU—this serene retreat offers character, convenience, and comfort.