Guesthouse holiday rentals in Lake County

Guesthouse in Deer Island

A screened patio area is shown, featuring a private pool surrounded by an expansive deck. Comfortable seating arrangements are visible, along with lush plants and natural light streaming in from large windows overlooking the wooded landscape.

4.96 out of 5 average rating, 138 reviews

Sapphire Cottage - sleeps 6, on 5 acres with canal

Escape to Sapphire Cottage, a 5-acre wooded retreat with a private canal boat dock. Relax by the shared pool, fish from the dock, or enjoy a BBQ at the firepit. Our cozy cottage features a queen master, 2 sofa-beds, a full kitchen, and dining for 6. From meeting our farm animals, biking, kayaking, or reading in the gazebo, there is something for everyone! We live in the main house across the way and are happy to help while ensuring you have a peaceful stay. Come make lasting memories with us!

5 out of 5 average rating, 125 reviews

An exterior view of the guesthouse displays a quaint two-story structure with a black garage and a welcoming front porch. Surrounding greenery provides a natural setting, enhancing the privacy of the location. The two upper windows are adorned with large curtains.

Guesthouse in Ocoee

NEW 1BRM Guesthouse | King Bed | Central Florida

Nestled in a private and central location, this newly constructed space offers everything needed for a relaxing stay. The space is perfect for up to four guests, featuring a king size bed, full kitchen, and smart TVs in every room. Enjoy the convenience of high-speed Wi-Fi, a spacious shower, washer / dryer, and a private driveway. Located close to Downtown, Theme Parks, the Stadiums, I-Drive, Wekiva Springs, Shopping, Dining, and More! Everything needed for your short term or long term stay.

4.89 out of 5 average rating, 100 reviews

A modern single-story home is presented with a well-maintained front lawn and a driveway accommodating a dark-colored pickup truck. The exterior features light-colored siding and a garage door, complemented by a clear blue sky overhead.

Guesthouse in Leesburg

Beautiful house in Leesburg FL

Beautiful home in Leesburg, FL, offering all the amenities and services needed for a wonderful stay. Located near Venetian Gardens Park, Emeralda Marsh Conservation Area, Flat Island Preserve, The Villages, and just minutes from popular stores like Wal-Mart, Target, Publix, Dollar General/Tree, Ross, TJ Maxx, HomeGoods, Belk, Marshall’s, and more. Please note, for security purposes, a doorbell camera is installed facing the entrance. It only monitors the exterior for your safety and privacy.

A cozy sleeping area is highlighted by two queen-size beds, each adorned with checkered yellow and white blankets. A lamp on a nightstand provides gentle illumination, and natural light filters through the window, which is fitted with blinds.

4.96 out of 5 average rating, 272 reviews

Cozy Buttercup Cottage!

Cozy 1/1 cottage- independent building, + nice breakfast kitchen, dining, & living room, great screened porch. 4 minute drive from Renninger’s, 5 minutes from Mount Dora City Hall Area where you'll find unique shops, restaurants, antiques, art museums, galleries, marina, parks, & many activities! *32 min/ Universal Studios & Island of Adventure, 43/ Magic Kingdom, 40 min/ Orlando Intl. Airport, 36 min/ Sanford-Orl Airport, 18 min/ Rock Spring, 48 min/ Silver Glenn Spring & much more!

A covered porch is showcased, adorned with climbing plants and vibrant foliage. Two sets of double doors lead into the cottage. A mix of potted plants and outdoor seating arrangements provides a welcoming atmosphere, inviting guests to enjoy the surrounding natural beauty.

4.87 out of 5 average rating, 346 reviews

A Lakeshore Cottage vintage 1926

What's new for 2019 a brand new dock and fishing pier. Additional boat docking available. Brand new Central Cold & Dependable Air Condition- Brand new 8 foot tall privacy fence & gate, parking pad beside cottage. -Eco Smart: lock, cork floors, instant hot H2O, solar lighting, copper sink, antiques, refurbished architecture ,charming! 2 nights/festivals ABSOLUTE RESTRICTION to ANIMALS! NO EXCEPTIONS. DO NOT Instant book if you are with any animals. Sorry allergies don’t allow.

A bright living space is presented with a large window allowing natural light to illuminate the room. A compact kitchen area features a white refrigerator and a granite countertop. A cozy gray sofa and two barstools complete the layout, creating a comfortable environment for relaxation.

4.89 out of 5 average rating, 217 reviews

Lake Dora Cottage!

We are located 1 house behind Lake Dora's lakefront, only a 1 mile scenic drive to Downtown Mr. Dora! We renovated this vintage lakeside cottage. It was originally a 1940's fish camp! The Cottage is detached from the main home with an enclosed private patio. The shoreline of the lake is PRIVATE PROPERTY WITH PRIVATE DOCKS. Guests have public access points. ****SERVICE ANIMALS ARE NOT ALLOWED*** We live on the property and therefore, it is not considered a public accommodation.

4.98 out of 5 average rating, 169 reviews

A bright and inviting living area showcases a light-colored sofa with neutral-toned throw blankets. A wall-mounted television is positioned above a contemporary media console, while natural light filters through two windows covered with sheer curtains.

Guesthouse in Clermont

Coastal Cottage in Clermont

Welcome to our newly renovated coastal cottage! Located in the heart of Clermont, only 1 mile from downtown, the south lake trail, & only minutes from all of the best restaurants, shopping, & coffee shops in Clermont! This is the perfect location for triathletes in training or families visiting Disney World (or any of the theme parks) – Orlando’s best attractions are less than 30 miles away! This sweet & sunny lakeside studio has everything you’ll need for a comfortable visit!

4.98 out of 5 average rating, 127 reviews

Guesthouse in Clermont

Charming Downtown Apartment - Walk to Everything

Stay in the heart of historic downtown Clermont- steps from the lakefront, breweries, shops, & dining. This light-filled, stylish apartment above our garage offers cozy aesthetics, comfy beds, a double shower, two spacious bedrooms, and a smart TV. Thoughtfully stocked for a stress-free stay, with garage storage for your bikes or paddle gear upon request. More than a stay—we proudly offer a distinct Clermont experience. We hope you love our charming town just as much as we do!

4.94 out of 5 average rating, 109 reviews

A small, charming retreat is nestled among large, sprawling oak trees and lush greenery. A gravel path leads to the cabin, surrounded by ferns and undergrowth. A bicycle is parked nearby, adding to the serene and natural setting.

Guesthouse in Tavares

Peaceful, adorable, guest cottage on Apopka Canal.

This special place with an "out in the country" feel is actually close to everything, making it easy to plan your visit. It is close to the cute shops and restaurants of Mt. Dora and Tavares, yet only an hour from all the attractions in the Orlando area. This 15 acre peace of paradise is right on the Apopka Canal with easy access to the Harris Chain of Lakes. Launch your boat from the boat ramp just across the canal from The Acorn at Lake Jem park.

4.91 out of 5 average rating, 159 reviews

A wooden walkway extends from the dock to the cottage, surrounded by a lush green lawn. The cottage features a screened-in porch, and trees provide shade on the property. Reflections of the surroundings are visible on the calm water.

Guesthouse in Tavares

Private cottage on Lake Saunders

This very private cottage is located on Lake Saunders and is perfect for a fishing get away or just spending some quiet time on the water. In just three steps off of the patio, you are down on the walkway out to the dock. Grocery stores and restaurants are very close by. Close to Mount Dora shopping and dining, this little gem offers a quiet, nature filled experience. Pets are welcome as long as they are on leash outside.

A charming kitchen features a bright red retro refrigerator and a compact microwave, with wooden countertops providing ample workspace. White cabinetry offers storage, while black and white patterned tiles complete the floor. A coffee maker is prominently displayed, adding to the functional design.

4.98 out of 5 average rating, 176 reviews

The Idle Hour Cottage - Walk to Downtown!

Idle Hour is a newly renovated cottage style 1 bedroom/1 bath unit. Located within walking distance to downtown, the marina, several parks, and Lake Dora. Enjoy the quaint neighborhoods, dining, shopping, or attend one of the year round festivities. Relax and enjoy the nostalgia of yesteryear while exploring downtown or relaxing in the courtyard with a glass of wine around the firepit.

A shared outdoor space is featured, containing a pathway of light-colored stones leading to a cozy seating area with two lounge chairs. Lush greenery surrounds the area, complemented by a large umbrella offering shade. The exterior of the efficiency unit is visible, displaying a welcoming entrance.