Vacation rentals in Sugarloaf Mountain

Find and book unique accommodations on Airbnb

Top-rated vacation rentals in Sugarloaf Mountain

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

0 of 0 items showing

1 of 3 pages

Top guest favorite

A bright living area features a light gray sofa adorned with yellow and blue cushions, accompanied by a comfortable recliner. A decorative round ottoman sits in the center on a floral area rug. Natural light enters through two large windows, complemented by light-filtering curtains.

Home in Winter Garden

4.97 out of 5 average rating, 121 reviews

Experience Downtown Winter Garden, One Block from It All

This 1920's home has been fully updated to include new kitchen, bath, fixtures, appliances, and more. The home has 2 bedrooms with one having a king bed and the other a queen bed. Beds feature super comfy Tuft & Needle mattresses ! Kitchen covers all of your basic cooking needs, has stainless appliances, refrigerator with ice maker, and Keurig coffee maker. The dining table comfortably seats 4 and is perfect for a meal or to use as a work space. New full size washer and dryer in carport laundry room. Grab a bottle of wine from Tony's less than 1 block away and relax in the screened-in front porch. Depending on the season grab a Valencia orange off the citrus tree in the back yard. You can use the entire home! There are 2 spacious bedrooms, 1 bath, dining room, kitchen, and a full washer and dryer in the laundry room (located in the carport). Owners live less than a mile away and are available as needed. We can meet you if you need anything! Just a few short steps from the famous Farmer's Market, Crooked Can Brewing, the Plant Street Market, the West Orange Bike Trail, Garden Theater, countless restaurants, and all that Downtown Winter Garden has to offer. This historic home is the perfect escape from the bustle of the tourist district, less than 30 minutes to Disney World, 25 minutes to Universal Studios, 30 minutes to Sea World. You can easily walk the 1 block to Plant St where most of the amenities of Downtown Winter Garden are located. You'll be just 25 minutes from Universal Studios and I-Drive via the Turnpike and 25 minutes from Disney via hwy 429. Also if you are into biking you can rent them at Wheel Works or the West Orange trail head and hit the famous West Orange Trail. There is a 2 car covered carport on site. Across the street from an elementary school so during the school year, there is some traffic in the morning and afternoon. Please be mindful and a good neighbor!

Top guest favorite

A coffee station is set up with a variety of coffee options and accessories. A brewing device and a kettle are displayed alongside jars containing sugar and other condiments. Decorative elements include a wall sign, a mirror framed with greenery, and a small plant.

Home in Montverde

4.96 out of 5 average rating, 139 reviews

The Legacy House - your home away from home.

Just a block away from the South Lake Bike Trail System, 18 minutes from beautiful Lake Minneola, and a mere 20 miles from the Disney Parks, and 5 minutes from the Bella Collina wedding venue, this peaceful neighborhood home will be a perfect spot to rest after a full day of fun. This is an ideal spot if you're coming for cycling events, fishing competitions, a wedding or simply to enjoy the most beautiful part of Florida! We hope you chose to book with us; it would be our pleasure to host you!

Top guest favorite

Guesthouse in Leesburg

4.98 out of 5 average rating, 388 reviews

Silver Lake Guest Pool House

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 grocery 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

Guest favorite

A circular fire pit surrounded by wooden Adirondack chairs is illuminated by a warm glow. The brick patio is partially covered with fallen leaves, creating a cozy outdoor space for gatherings. Soft shadows play across the scene, complementing the inviting atmosphere.

Home in Minneola

4.98 out of 5 average rating, 124 reviews

Cozy Studio Near Disney/Universal/Training center

This cozy stylish studio, detached guest house is perfect for short-term or extended stay in the beautiful city of Minneola. Sleeps 2, can accommodate up to 4. Features a large backyard and a fire pit. Close to Downtown Clermont, National Training Center, and 35 minutes to Disney World and other major attractions. This tranquil space features a queen bed with 3" memory foam mattress topper and a spacious living space that has a Multi-Functional Sofa that converts into a Bed.

Top guest favorite

A treehouse is illuminated by warm string lights, nestled among large branches under a deep blue sky. The structure features large windows allowing views of the surrounding greenery, with a cozy seating area visible inside. A wooden walkway leads to the entrance.

Treehouse in St. Cloud

4.96 out of 5 average rating, 980 reviews

TreeHouse in the Cloud, (Close toTheme Parks

The treehouse is a private getaway for a couple that want to experience the magic. Check out video tours on U-Tube. Type in Treehouse in the Cloud. There have been several movie and other photo shoots done on property. Please text request and details, and we can negotiate fees. Our other AirBnB is just next door; Country gem horses close to Theme parks [link] Which is 1,000 sq ft and sleeps six.

Guest favorite

The loft area showcases natural wood paneling reaching towards the peak of the A-frame structure. A minimalist bench is positioned next to a potted plant, providing a serene spot in front of a large window that frames the surrounding greenery.

Home in Ocala

4.96 out of 5 average rating, 180 reviews

Cozy A-Frame Retreat w/ hot tub!

Escape to our cozy A-frame cabin, nestled amidst the serene beauty of nature. Just 10 mins from Santos Trailhead and 35 from Rainbow Springs! After a day of exploration, unwind in the private hot tub, gather around the bonfire pit for s'mores, or snuggle by the fireplace and stream your favorite movie. Whether you seek a romantic retreat or an extended family getaway, our A-frame cabin promises the perfect blend of nature's tranquility and modern comfort!

Top guest favorite

Cottage in Clermont

4.9 out of 5 average rating, 111 reviews

Beautiful country house

Take the whole family to this fantastic place with many areas for fun. we have 5 acres of land just for you, beautiful country house in the only hills of the state of Florida, you will enjoy the tranquility, privacy, connection with nature and witness a beautiful sunset unparalleled, stay and observe the stars, spaces suitable for unique souvenir photos. Ideal area for cycling and walking. NOTE: if you want an event check our rates first

Top guest favorite

A serene view of a secluded yellow house set against a backdrop of lush greenery. The image captures the approach along a quiet road, flanked by tall trees providing shade, creating a sense of privacy and tranquility.

Guest suite in Montverde

4.98 out of 5 average rating, 201 reviews

Green Mountain Getaway (No indoor Smoking or Pets)

(Non Smoker & No Pets) A secluded lot surrounded by FL’s beautiful tropical landscape. Golfer? We are 3 min. from the beautiful Bella Collina's luxury 18 hole golf course, a Nick Faldo design. Also 8 min. from Sanctuary Ridge Golf Club, a more affordable option. Biker? “Killarney Station", is an affordable place to rent bikes or bring your own to ride the beautiful 26 mile trail. 28 minutes to all the attractions!

Top guest favorite

Guesthouse in Orlando

5 out of 5 average rating, 249 reviews

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!

Top guest favorite

An Apple desktop all-in-one computer is positioned on a wooden desk, featuring a colorful abstract screensaver. A white keyboard and mouse accompany the setup. A vase with pink and yellow artificial roses adds a touch of color to the scene.

Guest suite in Kissimmee

4.95 out of 5 average rating, 118 reviews

It's too much like a elegant mini-hotel (5)

It's too much like a elegant mini hotel with rich artistic atmosphere！ All the pictures on this page are a reflection of the real condition of the house. All the furniture has been carefully selected, and comfortable mattress and pillows will quickly accompany you into sweet dreams. The biggest feature of this house are comfort, economy and convenience.

Top guest favorite

Home in Clermont

5 out of 5 average rating, 117 reviews

Cozy Home near Waterfront Park

This newly constructed unique and cozy home sits in the heart of lakes near downtown, shops, restaurants, and breweries. It is surrounded by greenery that lets you relax and wind down in a tropical backyard. It is within walking distance to the lake beach, biking trail, splash pad, and playground. There are plenty of activities for you to enjoy!

Guest favorite

An open entryway features a staircase leading to the upper level, alongside a modern bar counter with stools. A sleek cabinet is positioned against the wall, and natural light fills the space through a nearby front door and window.

Cottage in Mount Dora

4.96 out of 5 average rating, 173 reviews

Cozy Cottage - Walk to Historic Downton-King Bed

Kick back, relax, and enjoy this newly remodeled Cozy Cottage! Located within walking distance (3mnts approx) of the Historic Downton Mount Dora where you will enjoy shopping, dining, festivals, fishing, boating, tours, and sightseeing along the beautiful lakes. in this calm, stylish space.

Vacation rentals for every style

Get the amount of space that is right for you

Hotels

Stylish accommodations and amenities

Unique stays

Spaces that are more than just a place to sleep

Homes

Comfortable places with all the essentials

Popular amenities for Sugarloaf Mountain vacation rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Other great vacation rentals in Sugarloaf Mountain

Top guest favorite

The exterior of a modern house is shown at night, with soft lighting illuminating the entrance. Two white chairs and a small table are set on the porch, surrounded by plants and flower beds, enhancing the inviting appearance of the home.

Apartment in Belleview

4.95 out of 5 average rating, 120 reviews

Solomon's porch entire apartment

MadisonRating, 5 stars3 weeks ago

this was my partner and i’s first air bnb where we stayed in the house with the host so we were a little nervous… but we LOVED the space! very private, cozy, super clean, with a nice sized tub! if we’re back in the area we’ll definitely try to stay here again. anna was kind and extremely helpful during our stay.

Guest favorite

Aerial view of a recreational area surrounded by lush greenery, featuring a centrally located pool area with lounge chairs. Pathways meander through the landscape, leading to a natural pond. Several buildings with sloped roofs are positioned around the pool, enhancing the scenic environment.

Home in The Villages

4.95 out of 5 average rating, 20 reviews

Cheerful King Bed Home in the Villages

BobbyRating, 5 stars4 weeks ago

Amazing host, amazing location, amazing property and amazing value!

Guest favorite

The bathroom features a walk-in shower enclosed by a blue and white patterned curtain. A recessed shelf displays three bottles of toiletries, while two neatly folded white towels are hung on a nearby rack. The walls are tiled with light-colored marble, creating a clean and contemporary look.

Guesthouse in Orlando

4.92 out of 5 average rating, 226 reviews

"Modern Suite"

VeronicaRating, 5 stars1 week ago

Great stay as always. William is always friendly and responsive with any needs we may have. My husband and I have stayed at Williams’s place four times and will definitely stay in the future.

Top guest favorite

A serene sunset is captured over a calm lake, reflecting vibrant hues of orange and purple in the water. A dock extends into the lake, with silhouettes of two people sitting at the edge, surrounded by soft grasses and distant trees.

Guesthouse in Groveland

4.93 out of 5 average rating, 80 reviews

The Blue Apartment - Country living & lake access.

MRating, 5 stars3 months ago

The Blue Apartment was exactly as described and the setting with access to Lake Emma was very peaceful. The apartment was comfortable and clean and the kitchen had what we needed. Thanks for your responsiveness to all my requests!

Guest favorite

A modern coffee maker is positioned on a marble countertop, highlighted by a decorative white ceramic pineapple and two translucent glass canisters. The coffee maker features a sleek design with a water reservoir, indicating it is ready for use.

Home in Mount Dora

4.93 out of 5 average rating, 69 reviews

1920's Boho Bungalow | Walk+Bike to Downtown

EmilyRating, 5 stars1 week ago

This cozy cottage was so perfect. The clawfoot tub was to die for. It was so peaceful and relaxing. Tara was very responsive. We had no issues the entire stay. It was beautiful.

Top guest favorite

Apartment in Winter Garden

4.9 out of 5 average rating, 147 reviews

Stay A While

PaulRating, 5 stars3 weeks ago

This is the second time my wife and I stayed here and both stays were exceptional. The place is clean, with beautiful views of the farm with horses. Quiet, with all amenities needed, and a beautiful pool that we enjoyed... we would happily recommend this place and the next time we are in the area, we would gladly book this place again!

Guest favorite

A private outdoor shower features a galvanized metal tub surrounded by natural elements. Lush greenery and a wooden structure enhance the serene environment, while vibrant purple flowers add a touch of color. Gray gravel covers the floor, contributing to the rustic aesthetic.

Dome in Davenport

4.91 out of 5 average rating, 98 reviews

Modern Domes | Pool | Hot Tub- Private Retreat!

AdrianaRating, 5 stars3 days ago

We had a wonderful stay at this cabin yesterday! The place was super safe and incredibly comfortable, making it the perfect getaway. Everything was clean, cozy, and well-maintained. We felt right at home and appreciated the peaceful surroundings. Highly recommend for anyone looking for a relaxing and secure place to stay! We hope to come back soon ❤️

Top guest favorite

Two ceramic mugs adorned with dragonfly designs are positioned on a round woven tray beside a light blue pitcher. The overall arrangement conveys a calm and inviting setting, perfect for enjoying beverages.

Cottage in Clermont

4.97 out of 5 average rating, 79 reviews

A-Frame Cottage near Disney, Universal, & Lakes

PatchaneeRating, 5 stars1 month ago

This place matched the description perfectly. The decor is charming and inviting. Its location is also very convenient, with easy access to various attractions.

Show all

Vacation rentals in Sugarloaf Mountain

Top-rated vacation rentals in Sugarloaf Mountain

Vacation rentals for every style

Popular amenities for Sugarloaf Mountain vacation rentals

Other great vacation rentals in Sugarloaf Mountain

Destinations to explore