Vacation rentals in Havana

The Country Cottage & Pool

King Bed,2.65 acres,Private pool,Dogs OK-$50 non refundable pet fee. 15 min to Tallahassee for sport events, colleges, legislation & business. A taste of Old FL with country breezes & wide open spaces. Stroll to quaint antique shops & eat in our cute cafes. Learn about “The Old Spanish Trail” & the many antique tobacco barns in the area. Cool off in our lovely pool or read under sprawling centuries old Oak trees. End the day at the firepit with a glass of wine or cup of cocoa. Relax & recharge!

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.

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.

Quaint Craftsman Downtown Havana

Nestled on the outskirts of downtown Havana, our home offers a quaint escape just a 5-minute stroll from charming storefronts. Enjoy local gems like Gocki’s burgers, Oscar’s Italian Eatery, and Off the Rails Irish Pub. Antique enthusiasts will love The Twisted Pineapple. Alongside Havana's unique blend of small-town charm, there is a grocery store and fast-food chains. Only 15 miles from downtown Tallahassee, relish the Hallmark feel of Havana while having easy access to big-city amenities.

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.

Little House on Broughton Downtown Bainbridge Stay

Located just four blocks from beautiful downtown Bainbridge, this one bedroom, one bath historic shotgun house was recently moved to Broughton Street from across town and fully renovated by your host. Enjoy a taste of an original tiny home with big personality! Home includes free wifi, fully equipped kitchen, and tips from your host on favorite local stops. Pet friendly stay perfect for walks through historic downtown Bainbridge for pets under 50 pounds with a $75 pet fee.

Mi Casa Su Casa

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!

Smart Home Near FSU, Big Backyard, Family Friendly

Modern 4BR smart home in Tallahassee, minutes from Florida State University (FSU), FAMU, and downtown. Ideal for game-day weekends, graduations, family visits, and group getaways. Minimalist modern interior with 4 bedrooms, 3.5 baths, and a spacious lanai with patio lounge chairs. Large fenced backyard surrounded by lush greenery, perfect for kids, pets, and outdoor gatherings. BBQ grill and outdoor dining available. Free parking and smart home features throughout.

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.

Historic Havana's Horseshoe Bungalow!

Stay in the heart of downtown Havana at the Horseshoe Bungalow, a renovated 3BR/2BA home with modern style and cozy charm. Enjoy a full kitchen, inviting living room, and updated baths. Sleeps up to 6 with comfortable beds and luxury linens. Outside features include a private carport with an EV outlet, perfect for charging your electric vehicle. Walk to shops and cafés or relax in your own stylish retreat.

The Cottages, Unit 3

Discover a delightful getaway surrounded by nature at The Cottages, Unit 3. This cozy one-bedroom, one-bathroom haven is perfect for couples or small families seeking a peaceful getaway. With its serene surroundings and modern amenities, you'll find everything you need for a relaxing stay. Located 20 minutes from Tallahassee, 20 minutes from Bainbridge, GA and 45 minutes from Thomasville, GA.

Sienna Lee Gardens: A Beautifully Renovated Home

Relax and unwind in this beautiful 4 bedroom/3 bath home nestled on 20 acres of picture perfect live oaks, organic blueberry orchard, and abundant wildlife. There are so many places for entertaining including a large swimming pool. There's a fully equipped kitchen, luxury beds and hotel quality linens. Every room has cable TV and internet throughout the house.