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, 139 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!

A charming dining area is set with a vase of red roses and blue hydrangeas. The table features elegant dishware, including floral-patterned plates and cups, accompanied by fresh strawberries and cookies. Textured cushions add comfort to the inviting seating area nearby.

4.99 out of 5 average rating, 173 reviews

Private Cottage in Mount Dora's Historic District

The Wishbone Cottage is a private one-bedroom bungalow located in the heart of the historic district of Mount Dora, a quaint village over 140 years old that overlooks Lake Dora. Nestled between palm trees and birds of paradise and surrounded by a privacy fence which offers seclusion and, at the same time, convenience to Mount Dora's abundant dining, shopping, and festivities, the cottage is the guest house of a larger historic bungalow. Please allow two day notice to book. Check in 3:00-6:30

4.98 out of 5 average rating, 431 reviews

The inviting exterior features a two-story home framed by lush green grass and mature trees. Arched windows and a symmetrical design enhance the charm, while a driveway leads to the front entrance, providing easy access to the peaceful surroundings.

Guesthouse in Leesburg

Silver Lake Guest Pool House Very Private !

The Silver Lake Pool Guest house Is your home away from home 1400 sq feet plenty of room! The pool house is a peaceful place to relax or take a swim in a large salt water pool . Mt Dora Tavares, Eustis 10 to 15 minutes away from Pool house Forty five minutes Daytona, Tampa Smyrna beach and parks Minutes from food stores restaurants malls Full kitchen also grilling. We are happy to help you with your needs ! Home is great for couples families, solo adventurers, and business travelers

4.98 out of 5 average rating, 135 reviews

A serene pool is surrounded by lush greenery, featuring a stone patio. Two white lounge chairs are positioned under a large umbrella, providing shade. The scene is set against a clear blue sky with a few fluffy clouds, enhancing the peaceful ambiance.

Guesthouse in Longwood

"Winnie's Place" A Peaceful Guesthouse with Pool.

Share the quiet backyard and pool with your hosts. Half was between Disney & the beaches. 12 years & older only. Sofa extends to a single bed. Minutes from Interstate-4. NOT a heated pool. Wheelchairs are fine. Driveway Entry gate 39"- Breezeway to Ramp entrance 32"- Slider Entrance 33"-Bedroom door 35"-Shower (no step) 35"-Laundry 32"-Closet 35"-Queen bed 29"-standard cabinets. We are not Handicap Certified but most wheelchair guests have not had issues. Grab bars are in the bathroom.

4.96 out of 5 average rating, 274 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, 348 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, 222 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.

4.95 out of 5 average rating, 111 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, 162 reviews

A scenic view from the patio captures a wooden dock leading into Lake Saunders, bordered by lush greenery. A glass-top table with chairs is positioned in the foreground, providing a serene space to enjoy the outdoor setting. The sky is filled with soft, fluffy clouds.

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.

4.99 out of 5 average rating, 286 reviews

A private pool area reveals clear water surrounded by lounge chairs and tropical landscaping. An umbrella provides shade over the seating area, while a grill and bar are positioned nearby under string lights, creating a relaxing outdoor environment.

Guesthouse in Orlando

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!

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, 182 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.