Places to stay near Historic Downtown Sanford

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Top-rated vacation rentals near Historic Downtown Sanford

Guests agree: these stays are highly rated for location, cleanliness, and more.

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Guest favorite

A spacious bedroom is shown, featuring a large bed with neutral bedding and pillows. Two bedside lamps provide soft lighting. A chair with a throw blanket sits in the corner beside a tall plant. Artwork hangs on the walls, and a window with sheer curtains allows natural light.

Home in Sanford

4.94 out of 5 average rating, 125 reviews

Bright & Airy in DowntownSanford

Beautiful, modern, and immaculately clean place with character and small town charm located in the very heart of historic downtown Sanford. Only steps away from the best dining and entertainment, and just a short drive away from all that Orlando has to offer! You will love the two spacious bedrooms, each fitted with luxurious king size beds and their own workstations. The rooms are split on either end of the home for extra privacy. Make a meal or pour a drink in the lovely fully stocked kitchen.

Superhost

A historic home is showcased from the front, highlighting its green exterior and large porch. Colorful landscaping features vibrant flowers and lush greenery, providing an inviting entrance. A paved walkway leads to the porch, surrounded by trees offering shade.

Home in Sanford

4.82 out of 5 average rating, 249 reviews

Dr. Strickland Home, Sanford Business District

This beautiful historic home has a unique history and is located in the heart of downtown Sanford. Please note, this home is NOT in a residential neighborhood. Centrally located between Daytona Beach and Orlando/Disney. Nearby are the Central Florida Zoo, Seminole Sports Complex, Civic Center, & numerous family-owned restaurants and watering holes, even lakefront dining! Minutes from the Orlando-Sanford Airport, (SFB), Amtrak Autotrain, I-4, & the Sunrail. There is also a free local trolley!

Top guest favorite

The exterior of a newly built home is displayed, featuring a modern design with a stone accent wall and large windows. The front porch is covered, providing an inviting entrance. A grassy area surrounds the home, with trees in the background enhancing the natural setting.

Home in Sanford

4.99 out of 5 average rating, 114 reviews

Sanford Get Away Casa

The whole group will be comfortable in this spacious and newly built home in downtown historic Sanford, FL. Less than 10 minutes to the Sanford International Airport, this 3 BR, 2 BA, new stylish contemporary home is loaded with amenities to help make your stay enjoyable at Sanford Get Away Casa. All bedrooms have TVs, including family room and gaming room/office, which can be shut off from other rooms for a quiet space. Kitchen, family and dining rooms are an open space, great for entertaining.

Guest favorite

Guesthouse in Sanford

4.94 out of 5 average rating, 211 reviews

Little Hidden Cottage- Near Sanford Airport

Located in Sanford FL, our Hidden Little Cottage is a Private Studio Guest House with its own entrance, fence, features full kitchen & bath room, queen size bed, full size pull out couch & twin size travel bed, & provides flexible self check-in. We are located 7 minutes from the Sanford Airport and Boombah Sports Complex, 10 minutes to Downtown Sanford, I –4 & 4–17. We’re also central to many Central Florida attractions such as Natural Springs, Sandy Beaches, Theme Parks and Historic Districts

Guest favorite

The houseboat is docked alongside the marina, featuring a spacious upper deck covered by a red awning. Large windows provide visibility into the main deck. The waterway reflects the blue sky, with palm trees in the background, accentuating the serene marina setting.

Houseboat in Sanford

4.83 out of 5 average rating, 199 reviews

Houseboat - 60 FEET OF FUN!

Stay aboard this luxurious 2-bed/2 bath, 2-story "floating condo" docked 3 short blocks from Historic Downtown Sanford. Fish off the dock. Observe birds, turtles, and manatees. Bike or walk to town. Enjoy the lakeshore RiverWalk. See a play/catch a show at the historic theatre. Browse an art gallery. Enjoy the ecclectic mix of restaurants, bars, and shops. Feed a giraffe, try the zipline/aerial obstacle course at the Central Florida Zoo. PLEASE NOTE: THE HOUSEBOAT DOES NOT LEAVE THE DOCK.

Top guest favorite

A charming houseboat with a teal exterior is shown moored at a marina, reflecting in calm waters. The upper deck is accessible by a ladder, and neighboring vessels and palm trees form a scenic background.

Houseboat in Sanford

4.96 out of 5 average rating, 141 reviews

Downtown Marina Floating Home Historic Sanford

You'll love this unique romantic escape located in historic downtown Sanford! This is a nearly new built top of the line Houseboat and you will be amazed at all the amenities fit on this 12x40 floating tiny home. Nicely suited for one couple. One step to get in and then all on one level other than the upper deck. (Ladder) Max occupancy at any time is 4. Walking distance to downtown restaurants, shops and so much more. Note that this is a very small space if you are used to a full size home.

Guest favorite

A charming exterior of a single-story home is shown, featuring a light blue façade and two large windows. A clear pathway leads to the front entrance, framed by lush green grass. A porch with two red chairs invites relaxation beneath the expansive oak trees overhead.

Apartment in Sanford

4.92 out of 5 average rating, 120 reviews

The Bed & Brad

Kick back and relax in this calm, stylish space. Enjoy the splendors of Sanford’s historic district with its beautiful brick roads and magnificent oak lined streets dripping with southern Spanish Moss. Walk or ride to the downtown area where you can eat and drink till your hearts content. Enjoy a walk along the lake or stroll through the streets to look at glorious restored southern homes. The Bed & Brad offers you all the comforts of home where you can enjoy your stay at your own pace.

Guest favorite

Loft in Sanford

4.89 out of 5 average rating, 234 reviews

Jazz Loft

Premier location, steps away from historic downtown and one of the oldest houses in Sanford! • 1 dbl bed, upstairs • We’ve tried to create the most modern design we could imagine while incorporating the original fireplace and taking advantage of the dramatically vaulted ceilings and original beams which date back to 1894, and our love for jazz • Our goal is to exceed your expectations, provide a comfortable feeling like you are at home • you'll see why this is our most popular apt.

Top guest favorite

A serene view of Lake Mary is framed by a large tree and a white post. The sky transitions into vibrant hues as the sun sets, reflecting softly on the water's surface. A lamp illuminates the foreground, enhancing the peaceful lakeside atmosphere.

Guesthouse in Lake Mary

4.97 out of 5 average rating, 146 reviews

Sunset Cottage in Lake Mary, Florida

Located on beautiful Lake Mary, this completely renovated studio sized guest house offers beautiful sunsets over the lake from a private patio. A comfortable queen bed, stylish sitting area and fully stocked kitchenette make for a wonderful stay in the Lake Mary- Sanford area. Minutes from the Sanford airport, close to the Sunrail station and 45 minutes to either Disney World or the beach. Our guest cottage is a perfect place to visit. Please note: The cottage is lakeview only.

Guest favorite

A cozy living area is furnished with a sofa adorned in blue and neutral tones, accompanied by a woven chair. A wooden coffee table is placed in front of the sofa. A wall-mounted television is visible, with a light fixture illuminating the space.

Guesthouse in Deltona

4.86 out of 5 average rating, 133 reviews

Tranquil Hideaway

This serene home offers the perfect blend of comfort and convenience. Located just minutes from Green Springs State Park, you'll enjoy easy access to outdoor adventures. Inside, you'll find a spacious living area, a fully equipped kitchen, and comfortable bedrooms with queen-size beds. Ideal for remote workers, the dedicated workspace provides a quiet and productive environment. Whether you're seeking a family vacation or a romantic getaway, this home has everything you need.

Guest favorite

A welcoming living area features comfortable seating arrangements around a central ottoman. A large television is placed on a stylish console, with decorative plants and artwork enhancing the space. Natural light streams through windows, contributing to a bright, inviting environment.

Home in Sanford

4.97 out of 5 average rating, 179 reviews

The Cypress House

This beautiful 2 bedroom, 1 bathroom Ranch Style home is conveniently located 3.5 miles from the Sanford International Airport and Boombah Sports Complex. The inviting landscape and backyard where you can cool off in the rustic style stock tank pool or grill out and relax on the patio. The open floor plan creates a spacious feel and every finish was selected with care. For a glamping experience check out our other listing: https://abnb.me/z3XrgOSPNFb

Guest favorite

A converted garage is showcased as a billiard room, featuring a red felt pool table with polished wooden legs. Colorful artwork hangs on the black walls, and a stylish hanging light illuminates the space. A smart TV is mounted, visible for entertainment while playing.

Home in Sanford

4.9 out of 5 average rating, 110 reviews

The Billiard: close to downtown with fenced yard

Totally set up for fun, The Billiard House has a billiard room, plus air hockey/mini ping pong, foosball, tons of board games to keep the little (and big) ones entertained. The bedrooms each have a fun theme - Guardians of the Galaxy, Batman, and Star Wars. Location is perfect: one block from downtown Sanford’s breweries and restaurants, and only a 10-minute walk to the waterfront. It's about a 10 minute drive from Boombah Sports Complex.