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Cottage holiday rentals in Windermere

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Top-rated cottage rentals in Windermere

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Guest favourite
A vibrant sign welcomes guests to Calypso Cay, featuring colorful tropical motifs, including palm trees and a fish design. The surrounding landscaping is complemented by green foliage and flower pots, creating a cheerful entrance to the community.
Cottage in Kissimmee
4.95 out of 5 average rating, 211 reviews

Runaway Beach Club | Disney | Epic Universe

Welcome to our 2/2 PET FRIENDLY villa just 8 minutes to Disney! Nearby you will find Lake Buena Vista Outlets, Universal Studios, Disney Springs, Old Town, restaurants and more! Stay includes: Disney Costumes Wi-Fi Washer/Dryer Free Parking Access to shuttle to Disney 4 pools including kids area/Calypso Cay Pools withTiki Bar 24 HR Gym, Volleyball/Basketball Court Mini Putt Putt Kids items available upon request. Strollers, etc. Small Pet Fee added for fur friends with complimentary pet food.

Superhost
The kitchen features natural wood cabinets and stainless steel appliances, including a dishwasher and oven. An open shelving unit displays various kitchen items. A cozy entertainment area is equipped with a pool table. The sleeping area showcases a dark wood bed frame with a neatly made bed.
Cottage in Orlando
4.92 out of 5 average rating, 142 reviews

Lake House

Beautiful 2 bedroom 2 bathroom cottage overlooking lake. It is close to several other lakes & dog friendly parks. Comfort was the number one reason when choosing the furniture & mattress. Kitchen is fully equipped with coffee maker, keurig, toaster, microwave, cook top oven, refrigerator, washer, dryer and flat screen TV. Free wifi, cable TV, Max, Amazon & Neflix. You have one off street parking spot. Snacks & light breakfast provided. Please note there is an additional charge to use pool.

Top Guest favourite
A bright kitchen with white cabinetry and a modern stove is visible. Red floral curtains frame the windows, providing a cheerful ambiance. A dining area with a wooden table and chairs is present, along with open shelving displaying dishes and decorative items.
Cottage in St. Cloud
4.93 out of 5 average rating, 310 reviews

Country Gem, Horses, Close to theme parks

Our place is good for couples, solo adventurers, business travelers, and families (with kids). The cottage is handicapped friendly. We have available two ramps, elevated toilet and toilet chair, and hand bars. The shower has a shower chair, and pedestal sink. There are two sliding barn doors which will make the common areas into two semi private rooms. Check in is 3pm, check out is 11am. Canaveral National Seashore is 44 miles away. An island on the Atlantic Ocean, is a National Park.

Top Guest favourite
A themed kitchenette features a bamboo bar with high seating and colorful pendant lighting. The walls are adorned with tribal art and shelves hold various artifacts. Kitchen appliances, including a refrigerator and counter space, reflect a blend of modern convenience and cultural decor.
Cottage in Kissimmee
4.99 out of 5 average rating, 190 reviews

Tahiti Gil’s Mananui: Disney Poly & Tiki Inspired!

Aloha Adventurers! Welcome to Faré Mananui. Your passport to a far away tropical hideaway awaits, so get ready to grab your favorite Aloha shirt! Mananui was made for the Disney/Tiki ADULT in mind! Imagined by artist @TahitiGil & designed by @TyphoonTommy (Former Disney/Universal creative team & designer of the Suffering Bastard Tiki Bar in Sanford, Fl. Experience your next Adventureland/ Enchanted Tiki Room “story dwelling” adventure from the moment you step thru the door! - Kungaloosh!!

Top Guest favourite
The exterior of a renovated cottage is showcased, featuring a welcoming front porch with two wooden chairs. Potted plants are placed on the porch and along the walkway, while a wooden fence stands in the background, enhancing privacy.
Cottage in Winter Garden
4.99 out of 5 average rating, 184 reviews

The Heart of Winter Garden: Walk to shops & dining

Stay in a completely renovated 1937 cottage that's located in the heart of historic downtown Winter Garden. It's walking distance from all of the shops, restaurants, and events (including the #1 rated farmers market in the nation every Saturday) that make Winter Garden one of the most desirable cities in Florida. Sit on the front porch and watch as people bike and jog on the famous West Orange Trail, or rent a bike from the corner and join them. The home is close to all major highways.

Top Guest favourite
A living area features a light-colored sofa with accent pillows, complemented by a circular coffee table. A patterned rug in shades of red and beige adds warmth. Natural light enters through two windows with yellow curtains, and a front door is prominently displayed.
Cottage in Kissimmee
4.97 out of 5 average rating, 144 reviews

Cozy Orlando Area Cottage - 4 Miles to Disney

With Disney, popular attractions, restaurants, shops, and famous southern sunshine just minutes from your doorstep, we welcome guests to our cozy cottage for your vacation getaway. Our 1 bedroom, 1 bath cottage boasts modern amenities and entertainment options to help you relax during your stay. The cottage is located in a quiet, gated, resort community. Community amenities include an outdoor pool, hot tub, mini golf, game room, fitness center, planned activities, and tennis court.

Top Guest favourite
A charming white cottage is framed by a well-kept lawn, with a brick chimney visible on one side. Lush green shrubs and trees provide shade around the property, and a pathway leads to the entrance, suggesting easy access to the home.
Cottage in Davenport
4.99 out of 5 average rating, 113 reviews

Classic Cottage in country setting

Relax with the family in this peaceful setting. Short drive to the parks, shopping, restaurants. 10 minutes from Interstate 4. Walmart and Posner Park Shopping Center nearby. Patio area with fire pit and gas grill and lawn chairs. 2 car carport parking on premise. 2 bedroom w/HDTV's, 2 bath, fully furnished kitchen, dishwasher, breakfast nook, dining room, living room w/HDTV. Washer/dryer. Fully fenced 3/4 acre yard with plenty of room for kids to play. Self check in with keypad.

Top Guest favourite
Cottage in Orlando
4.97 out of 5 average rating, 101 reviews

Cozy Guesthouse w/ Outdoor Oasis

Kick back & relax in this cozy, private guesthouse featuring a fenced outdoor space with covered seating, electric grill, yard games & a fire pit. The guesthouse includes a king-size bed, 1 single bed, full kitchen, laundry, 2 smart TVs & ample parking. Located 3.5 miles from Moss Park which offers fishing, boating, wildlife, walks, & playground. Close to Lake Nona, Orlando Airport, & the USTA campus. Easy access to highways, with most Orlando attractions within a 40-minute drive.

Top Guest favourite
Cottage in Clermont
4.92 out of 5 average rating, 134 reviews

Beautiful country house

Take the whole family to this fantastic place with many areas to have 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 you will witness a beautiful sunset unparalleled, stay and watch the stars, spaces suitable for unique souvenir photos. Ideal area for cycling and hiking. NOTE: if you want an event, check first for our rates

Top Guest favourite
The cottage features a charming exterior with bright yellow siding and a classic gabled roof. Lush palm trees and manicured hedges frame the entrance, which includes a welcoming porch with yellow chairs. Large windows allow natural light to enhance the inviting facade.
Cottage in Citrus Ridge
4.98 out of 5 average rating, 125 reviews

1BD Cottage "Limoncello" in Margaritaville

Welcome to your own island-inspired oasis. Our charming cottage is the perfect home base for your next dream Orlando vacation. The unit comes with all the comforts from home but worlds away. Conveniently located minutes from the Disney parks, a state-of-the art water park and newly opened 196,000 square foot shopping and dining district with multiple dining food and beverage options & brand-new movie theater. All Pets Must Be Preapproved :)

Top Guest favourite
A yellow cottage is featured, with a welcoming entrance that includes a set of wooden steps leading to a covered porch. White railings frame the porch, while a ceiling fan hangs above. Lush greenery and flowering plants are positioned near the entrance, enhancing the overall charm.
Cottage in Kissimmee
4.95 out of 5 average rating, 515 reviews

Bright & Cozy Cottage Near Disney

My place located within 10 miles of: Disney World, Celebration, Universal, Water Parks, Old Town & Fun Spot USA's More than 70 Restaurants and Dining, Gifts Shop. My place is good for couples, solo adventurers, business travelers, and families (with kids). You’ll love my place because of In Our Cozy and Comfortable Sand Castle Cottage You'll discover that perfect Mix of High-Energy Fun and Laid Back Florida Lifestyle Right Here.

Top Guest favourite
Cottage in Kissimmee
4.97 out of 5 average rating, 121 reviews

Cottage of Charms

Step into the magic and reconnect with nature at this charming Cottage. This cozy Tiny Home is only 4 miles from the enchanting gates of Disney World. Surrounded by shops, dining, and pixie-dusted fun all within walking distance, you’ll feel like you’re in your own fairytale. When resting from your adventures, create magical moments right at home with the amazing amenities, and don't forget to visit our stunning pool.

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