Family-friendly holiday rentals in DeLand

The Monarch House, in the heart of downtown Deland

Welcome! This house was built in 1920 and has been beautifully restored. It's three blocks from the center of downtown Deland! Walk or take a quick bike ride to restaurants and shops. It is a large two story house (2,400sq. ft)! Ping pong, air hockey, foosball, checkers/chess table, cornhole, 4 bikes included, huge front porch for people watching, large natural gas fire pit, grill, basketball hoop, and so much more! The bunk room upstairs has its own separate livingroom too! Nothing compares!!

Rustic Retreat in the heart of Lake Helen

This charming rustic home has a lot to offer. It has many nooks where your family can unite and create moments for their memory buckets. Florida room allows you to observe nature and is a perfect spot for your coffee. The house has one master bedroom (king size bed) with attached full bathroom. It has a second bedroom with two built-in beds (twin and full size). There is a separate shower room and a separate restroom. Upstairs it has a 3rd bedroom with 2 built in twin beds and a 1/2 bathroom.

Cozy Cottage in DeLand

Enjoy a stylish experience at this cozy home in the heart of quaint, historic DeLand. This updated home offers the perfect blend of charm and chic modern living. Centrally located to the award-winning Mainstreet of downtown DeLand, & just a 7 minute walk from shops, diverse restaurants and brewery. The open plan design and large windows create a warm and spacious feeling. The house accommodates up to 5 guests making it ideal for families or adult groups visiting DeLand or Stetson University

Simple, clean two bedroom APT walk to Stetson (#4)

This is a second floor apartment in a 1925 building that was fully renovated in 2015. There's a full kitchen with everything you need for cooking. The screened in back porch contains the full sized washer and dryer that guests are free to use and the back door opens to a good sized back yard (shared space) and there's a private front balcony. The apartment is walking distance to Stetson University and about a mile from DeLand's award winning downtown. There is reserved parking for one car.

Persimmon Place, family friendly historic cottage

Come unwind in a piece of history. Our 1920s historic bungalow offers just that! We've renovated this home to provide all the comforts you expect, while ensuring its unique character shines through. You'll love our prime location, just a few blocks from the lively heart of Downtown and the beautiful Stetson University campus. Start your day on the front porch, perfect for enjoying the neighborhood, or find a peaceful retreat on the back porch overlooking the fenced yard – a haven for kids.

Mira Bella South

Tiny Home with full kitchen on a peaceful 13 acres in a small town. Owner lives on site, but the tiny home is away from the main house so it is private. Ideal for 2 guests, but there is a pull-out sofa which could be comfortable for one more adult or a couple kids. Room for more than one car or a trailer. (Not suitable for 4-legged travelers due to free ranging ducks, peacocks and close proximity to horses and miniature donkeys) (If your dates are unavailable, search Mira Bella North)

Walk to Stetson University & Downtown DeLand

Clara House is a 1920s home that has been beautifully restored. Located 3 blocks from Stetson Campus and downtown Deland. This home offers ample space to spread out and relax, with a fully equipped kitchen, pet friendly fenced in back yard. Clara house is 30 minutes from Daytona speedway and New Symrna beaches. Blue Springs state park is 6 miles away and 45 minutes to Orlando. 5 miles to Bridal Oakes, and directly across the street from north west square. This is a non smoking house!

“The Forty” in Central Florida

40min to Everything!!! Beautiful efficiency, sleeps 2 adults and two children comfortably! Fully furnished, with all the little details taken care of. Just pack your clothes and head to beautiful historic Deland, Florida! With so many attractions within driving, your schedule will be packed. There are many natural springs in the area to explore by kayak, boat or bike!! 40 min. to beaches, 40 min. to attractions!! We do accepts pets, the fees and registration must be paid on the app.

No Worries Carriage House, 5 min walk to Stetson

This second-floor carriage house is all yours. Located on a quiet street amidst historic homes. Walk to Stetson in 5 min. Downtown DeLand is an easy 15 min. walk. Your two bedrooms, full kitchen, private access will be great for a get-away for you and your guests. 42" flatscreen TV with cable and Amazon Prime with no ads. Wifi. The second-story banks of windows look out over beautiful, tropical plants. Space to work or relax. We look forward to you enjoying your stay with us.

DeLand Charmer- Near Daytona Beach and Orlando

Just minutes to the award winning Main Street and Stetson University. Ask me a question. I know where all the goodies are! Great location in between Daytona Beach and Orlando, the best of both worlds within just 30 minutes! You will enjoy the personal touches and decor this home has to offer. You will be pleased with these new cozy beds. Very quite and relaxing. The grocery store is within 1 block. We strive for excellent hospitality and want you to come back again and again.

The Cottage at True Trail Farm

Our studio Cottage is pet friendly and sleeps 2 comfortably. This is a tiny house where we have managed to fit all essentials for a relaxing stay. We are 5 minutes from historic downtown and 30 minutes to the World’s Most Famous Beach, Daytona Beach. Enjoy fresh eggs from our chickens in the morning before heading to the Springs for a cool dip or manatee watching only 10 minutes away.

Boutique Hideaway in DeLand • Steps from Downtown

Escape to this remodeled boutique hideaway steps from downtown DeLand. Enjoy a bright, thoughtfully designed space with a cozy living area, fully equipped kitchen, plush queen bedrooms, and private outdoor nook for morning coffee or evening wine. Walk to restaurants, shops, and local events, then return to comfort, privacy, and effortless relaxation. Well‑trained pets welcome.