Guest house holiday rentals in DeLand

1926 Spanish Carriage House Lower

Enjoy a shared but private compound resort in the heart of downtown Orlando! Centrally located and within walking distance to major events at the Kia Center, Dr. Phillips Performing Arts Center, restaurants, and downtown nightlife. Park on site, relax and enjoy all that this historic home has to share! Besides a fresh and clean private lodging, you'll enjoy use of the tropical pool, hot tub, gas grill, covered seating and dining area. A washer and dryer are just steps away for your use.

Little Hidden Cottage- Near Sanford Airport

Located in Sanford FL, our Hidden Little Cottage is a private studio guest house with its own entrance, 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

The Glass-Flower Cottage

This romantic cottage is perfect for some much-needed relaxation. Your private fenced-in yard has its own outdoor dining area, charcoal grill, paver walkway, and fire chiminea. Nicely located within 2 miles of Historic Downtown Deland, there are numerous unique shops, exquisite eateries, and exciting nightlife nearby. The famous Daytona Beach and Daytona 500 Speedway are 21-25 miles away. Enjoy a cup of coffee and relax a while. Don’t see availability, check out our other places!

Suite Retreat

Avoid blah hotels with high prices and stay in this luxe new apartment suite! It’s a perfect retreat in Central Florida. Located a short drive to activities, restaurants, & shops in Lake Mary or downtown Sanford - 45-55 min to Orlando theme parks or the beaches of New Smyrna. Ideal for a couple’s retreat or a getaway for one. Guests use office space designed for comfort & productivity. A cozy chair begs readers to curl up and read. The outdoor canopy hosts breakfast with birdsong!

Tropical Cottage & Garage 2 Miles from Blue Spring

This cozy spring escape sits privately behind a unoccupied garage among the quiet oak streets of Orange city. conveniently located 2 miles from Blue springs state park, 5 miles from Downtown Deland and 30 minutes from the beautiful beaches of Daytona and New Syrmrna. This property provides a unique connection to nature. Enjoy an outdoor bathroom experience with a shower under the stars. Blue Springs is now open for swimming & water fun as of May 23, 2025! Garage amenities included!

Cozy Guesthouse close to all

Keep it simple at this peaceful and centrally-located place. Just 1.4 miles from the beach and 1 block from Ormond’s pubs and restaurants; you can take a bike or walk to most of the best spots! Designed for ultimate relaxation and equipped with all you’ll need to enjoy your cozy home away from home. We have the beach, the restaurants, and rivers nearby for kayaking or boating! Go one way for beaches and breezy pub crawls and the other for walking paths and lazy river floating.

Livingston Pool House- In The Heart of Downtown

Welcome to the Pool House! Our newly renovated detached pool house is located in the heart of downtown Orlando, in the Lake Eola Heights Historic District. We are two blocks to beautiful Lake Eola and all the dining and entertainment that Orlando has to offer. The Pool House has everything you need for a relaxing time at home, yet all the entertainment at your finger tips! Downtown living with a tropical escape!

Hidden Gem - Cottage in Lake Helen

Nestled in a beautiful paved and gardened backyard space. My 640 sq/ft private cottage is behind my home in the small quiet town of Lake Helen, only a mile off of I-4. The cottage is filled with all the amenities that will make you feel at home. The cottage has one queen bed and the sofa bed is perfect for children. Also a pack and play for little ones. The cottage is perfect for two but will suit 4.

Cottage on horse farm

Casual cottage on horse farm in rural setting. Stroll through the flower gardens and paddock lanes of the 30 acre horse farm. Watch horses trained dressage. Country atmosphere but still only 10 minutes to grocery store, 5 minutes to restaurants, 15 minutes to historical downtown Deland, Stetson University & skydive Deland. 30 minutes to Daytona Speedway, 45 minutes to the beach. NO WI-FI