Holiday rentals with outdoor seating in Tallahassee

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.

Coastal City Cabin: a Cute Florida Getaway A-Frame

Picture this.. Spend the day fishing out on the coast or swimming in the world's largest freshwater spring then some fun in town with great eats & live music! Finish the night with a hot tub soak under the stars. No worries, you can do it all again tomorrow! Conveniently nestled between Tallahassee and the 'Forgotten Coast', our cabin is a perfect match for your adventure-filled vacation. A quick 15 minute ride from the Tallahassee airport has you enjoying the sunset from our rocking chairs.

15 walk to FSU/2 mile drive to Bragg & Capital

Come enjoy our Moroccan inspired getaway, The Casa Blanca! This beautifully decorated home is a quick 15 minute walk to the FSU stadium, a 5 minute walk to various restaurants, a 7 minute drive to FAMU, and a 10 minute drive to downtown. The home is equipped with TVs in each room, a fully stocked kitchen, a coffee bar, and shampoo and conditioner. Enjoy spending evenings relaxing on the newly built deck out back and have convenient access to two assigned parking spots in front of the home!

Historic Briarcliffe Cottage

This quaint two-bedroom stone cottage has all the comforts of home. It was built by a Scottish architect in 1939 with limestone quarried nearby in Wakulla. Full of historic charm; it is listed on the local historic registry & has been lovingly restored and furnished for use as a guest house. Beautiful hardwood floors, original artwork, and modern touches for guest comfort. Close to downtown, approximately 1 mile from the capital building and 1.5 miles from FSU in historic Old Town.

Cozy Football Retreat Coffee FSU FAMU Walk to Doak

Park 2 cars and walk to FSU Doak Stadium! 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. 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)

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.

The Gathering @ Magnolia Hill (1 mile to Capitol)

The Gathering is located in one of Tallahassee's thriving downtown neighborhoods known as OLD TOWN. It is a quiet, mature residential neighborhood where we are "At Home in the Heart of It All". We are located less than a few miles from downtown, the Capitol complex, FSU, FAMU and TCC. We are also located near numerous restaurants, shopping, parks and Tallahassee Memorial Hospital. Walk, bike, drive or public transportation...all options...YOUR CHOICE!

Cheerful 4 Bdr Pool Home [4mile (10min) 2 Capitol]

This stylish place to stay is perfect for group trips. The home is fully equipped and literally minutes to everything. Its convenient location make this the ideal spot for You can enjoy lazy days by the pool (3ft to 7.5ft deep), laughed filled evening in our modern living room or just crash in the SUPER comfortable beds after a day out on the town. This home is 4 miles and a quick and easy 10 minute drive to the Capitol.

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.