This charming cottage is situated in Altamonte Springs, Florida, just a short distance from the Altamonte Mall and Advent Florida Hospital North, and within easy reach of Interstate-4, Orlando International Airport, and major theme parks. The cottage has received excellent user ratings, making it a popular choice for travellers. The cottage offers one bedroom and one bathroom, spanning 102 square metres and comfortably accommodating up to four guests. Enjoy a range of features including a private boat ramp, pedal boat, outdoor fire pit, hammock, and outdoor shower, perfect for relaxing and enjoying the outdoors.
Winter Park, FL
03/09 – 08/09
$278/nighttotal: $1390 (5 )
Romantic Lakefront Getaway With Balcony Near Downtown Orlando
1 2
cottage , Conway
This non-smoking cottage, situated by the water in Orlando, is a 13-minute drive from the Kia Centre and a 8-minute drive from Florida Mall. This one-bedroom, one-bathroom lodge accommodates two guests and features a garden, balcony, Wi-Fi, air conditioning, and a full kitchen, with lake activities and on-site parking readily available.
9.0 8 reviews
Winter Park, FL
17/06 – 23/06
$139/nighttotal: $834 (6 )
Lovely Spacious Guesthouse In Mills 50 District, Orlando
1 1
cottage , Orlando
This Orlando cottage, situated in Colonialtown North, is less than 1.6km from the Orlando Museum of Art and AdventHealth Orlando, and approximately 4.3km from the Kia Center. The self-catering property sleeps two guests in one bedroom and one bathroom, and includes in-unit laundry facilities, a hairdryer, and air conditioning.
9.9 113 reviews
Winter Park, FL
17/06 – 23/06
$217/nighttotal: $1302 (6 )
Cottage Retreat In The City
1 1
cottage , Orlando
This charming cottage is situated in the College Park neighbourhood of Orlando, a peaceful residential area close to the historic Dubsdread Golf Course, offering a tranquil escape whilst being within easy reach of urban amenities. The cottage has received excellent ratings for location, cleanliness and user experience. The cottage has one bedroom and one bathroom, comfortably accommodating two guests. It comes fully equipped with a kitchen, air conditioning, a terrace, a garden, and parking for one car.
Winter Park, FL
03/07 – 31/07
$242/nighttotal: $6776 (28 )
Walkable Quiet Lakefront Retreat Near Downtown Orlando With Private Patio
1 2
cottage , Conway
This Conway cottage offers a convenient base, located 11 kilometres from Lake Eola Park and 13 kilometres from the Kia Centre, with easy access to Florida Mall and Universal Orlando Resort. This one-bedroom dwelling accommodates two guests and includes amenities such as internet, air conditioning, a dryer, and ironing facilities, with essential toiletries provided.
8.2 11 reviews
Winter Park, FL
21/07 – 04/08
$158/nighttotal: $2212 (14 )
Downtown Cottage
1 1
cottage , Orlando
This Orlando studio apartment is conveniently located in downtown Orlando, offering easy access to major roads and within walking distance of numerous restaurants, and is close to Universal Orlando Resort and Universal Studios Florida (distances unspecified). The self-contained property sleeps up to six guests, features a fully equipped kitchen, a private bathroom with shower and laundry facilities, and benefits from air conditioning, parking and Wi-Fi.
9.8 37 reviews
Winter Park, FL
02/08 – 04/08
$381/nighttotal: $762 (2 )
The Coach House- Entire Home - 2 Bedroom/3 Bath Orlando Getaway!
2 6
cottage , Orlando
This charming cottage is situated in the College Park district of Orlando, just a 25-minute drive from Orlando International Airport and major theme parks like Disney, Universal, and The Outlets. It has received excellent user ratings, making it a popular choice for travellers seeking a comfortable and convenient stay. The two-bedroom, three-bathroom cottage offers 111 square metres of space, comfortably accommodating up to eight guests. Amenities include a fully equipped kitchen, a private garden, a terrace, high-speed internet, and a 52" HD TV with Roku, ensuring a relaxing and enjoyable stay for all.
Winter Park, FL
28/06 – 18/07
$518/nighttotal: $10360 (20 )
Eolas Zen
3 1
cottage , Orlando
This detached house is situated in Orlando's historic Lake Eola Heights district, a 3-minute walk from Lake Eola Park and within easy reach of downtown Orlando's dining and entertainment venues, including the Dr. Phillips Performing Arts Centre and the Kia Centre. This 3-bedroom, 2-bathroom property accommodates six guests and features a private swimming pool, an open-plan living area, a well-equipped kitchen, and eco-friendly amenities, with Universal Studios Florida and Universal Orlando Resort approximately 12 kilometres away.
9.5 118 reviews
Winter Park, FL
11/08 – 13/08
$173/nighttotal: $346 (2 )
Tiny Hidden Cottage
1 2
cottage , Longwood
The Hidden Tiny Cottage II is located in Longwood, offering a secluded retreat on the back side of a property on Beach Ave. The cottage has received excellent ratings for its cleanliness, location, and overall experience. This charming cottage offers a comfortable and private stay for two guests. It features a fully equipped kitchen, air conditioning, a Jacuzzi, a garden, a spa, a fitness centre, and parking, making it a perfect choice for a relaxing getaway.
9.0 24 reviews
Winter Park, FL
11/08 – 13/08
$376/nighttotal: $752 (2 )
Garden Cottage-swim/spa Sleeps 6 Ctrl Orlando Disney Universal Seaworld Beaches,
2 2
cottage , Altamonte Springs
This Altamonte Springs holiday home is conveniently located less than 1.6km from Cranes Roost Park and Uptown Altamonte, offering easy access to shops and restaurants, and within 56km of Orlando International Airport (MCO) and Sanford Airport (SFB). Sleeping six, this two-bedroom, one-bathroom property boasts a king and two queen beds, a fully equipped kitchen with island seating, a private garden, swimming pool, jacuzzi, and parking; an additional one-bedroom apartment is available upon request.
Best family friendly Winter Park, FL cottage rentals
Among the 12 accommodations in Winter Park, FL, here are the 2 best family friendly cottage rentals
9.8 37 reviews
Winter Park, FL
02/08 – 04/08
$381/nighttotal: $762 (2 )
The Coach House- Entire Home - 2 Bedroom/3 Bath Orlando Getaway!
2 6
cottage , Orlando
This charming cottage is situated in the College Park district of Orlando, just a 25-minute drive from Orlando International Airport and major theme parks like Disney, Universal, and The Outlets. It has received excellent user ratings, making it a popular choice for travellers seeking a comfortable and convenient stay. The two-bedroom, three-bathroom cottage offers 111 square metres of space, comfortably accommodating up to eight guests. Amenities include a fully equipped kitchen, a private garden, a terrace, high-speed internet, and a 52" HD TV with Roku, ensuring a relaxing and enjoyable stay for all.
9.0 24 reviews
Winter Park, FL
11/08 – 13/08
$376/nighttotal: $752 (2 )
Garden Cottage-swim/spa Sleeps 6 Ctrl Orlando Disney Universal Seaworld Beaches,
2 2
cottage , Altamonte Springs
This Altamonte Springs holiday home is conveniently located less than 1.6km from Cranes Roost Park and Uptown Altamonte, offering easy access to shops and restaurants, and within 56km of Orlando International Airport (MCO) and Sanford Airport (SFB). Sleeping six, this two-bedroom, one-bathroom property boasts a king and two queen beds, a fully equipped kitchen with island seating, a private garden, swimming pool, jacuzzi, and parking; an additional one-bedroom apartment is available upon request.
Best Winter Park, FL cottages with a garden
9.5 118 reviews
Winter Park, FL
11/08 – 13/08
$173/nighttotal: $346 (2 )
Tiny Hidden Cottage
1 2
cottage , Longwood
The Hidden Tiny Cottage II is located in Longwood, offering a secluded retreat on the back side of a property on Beach Ave. The cottage has received excellent ratings for its cleanliness, location, and overall experience. This charming cottage offers a comfortable and private stay for two guests. It features a fully equipped kitchen, air conditioning, a Jacuzzi, a garden, a spa, a fitness centre, and parking, making it a perfect choice for a relaxing getaway.
Winter Park, FL
03/07 – 31/07
$242/nighttotal: $6776 (28 )
Walkable Quiet Lakefront Retreat Near Downtown Orlando With Private Patio
1 2
cottage , Conway
This Conway cottage offers a convenient base, located 11 kilometres from Lake Eola Park and 13 kilometres from the Kia Centre, with easy access to Florida Mall and Universal Orlando Resort. This one-bedroom dwelling accommodates two guests and includes amenities such as internet, air conditioning, a dryer, and ironing facilities, with essential toiletries provided.
9.9 113 reviews
Winter Park, FL
17/06 – 23/06
$217/nighttotal: $1302 (6 )
Cottage Retreat In The City
1 1
cottage , Orlando
This charming cottage is situated in the College Park neighbourhood of Orlando, a peaceful residential area close to the historic Dubsdread Golf Course, offering a tranquil escape whilst being within easy reach of urban amenities. The cottage has received excellent ratings for location, cleanliness and user experience. The cottage has one bedroom and one bathroom, comfortably accommodating two guests. It comes fully equipped with a kitchen, air conditioning, a terrace, a garden, and parking for one car.
9.8 37 reviews
Winter Park, FL
02/08 – 04/08
$381/nighttotal: $762 (2 )
The Coach House- Entire Home - 2 Bedroom/3 Bath Orlando Getaway!
2 6
cottage , Orlando
This charming cottage is situated in the College Park district of Orlando, just a 25-minute drive from Orlando International Airport and major theme parks like Disney, Universal, and The Outlets. It has received excellent user ratings, making it a popular choice for travellers seeking a comfortable and convenient stay. The two-bedroom, three-bathroom cottage offers 111 square metres of space, comfortably accommodating up to eight guests. Amenities include a fully equipped kitchen, a private garden, a terrace, high-speed internet, and a 52" HD TV with Roku, ensuring a relaxing and enjoyable stay for all.
Frequently Asked Questions about cottages in Winter Park, FL
What would be a good 2-days itinerary for visiting Winter Park, FL?
On your first day, visit the Charles Hosmer Morse Museum of American Art, which has a fantastic collection of Tiffany glass. In the afternoon, take a stroll around the charming Park Avenue district, with its boutiques and cafes. On day two, explore the scenic Winter Park Scenic Boat Tour, and in the afternoon, visit the Kraft Azalea Garden, which is beautiful in spring.
What are the best cottage rentals in Winter Park, FL?
What part of Winter Park, FL is ideal for renting a cottage?
The area around Lake Maitland is lovely for renting a cottage. It's close to the downtown area, but still offers a peaceful, lakeside atmosphere. You can find some charming cottages on the east side of the lake, near the Winter Park Village.
What are the best cottage rentals with a pool in Winter Park, FL?
When is the best time to rent a cottage in Winter Park, FL?
The best time to visit Winter Park is during the spring (March to May) or autumn (September to November) when the weather is mild and there are fewer crowds. You'll find that cottage rentals are typically more affordable during these shoulder seasons.
What are the best cottage rentals with a jacuzzi in Winter Park, FL?
What are the can't-miss sights in Winter Park, FL?
You must visit the charming Park Avenue district, with its unique boutiques, art galleries, and restaurants. The scenic Winter Park Chain of Lakes is another must-see, offering opportunities for boating, kayaking, and paddleboarding. Don't miss the chance to explore the beautiful Mead Garden and the historic Rollins College campus.
What are the best cottage rentals for families and kids in Winter Park, FL?
Why consider renting a cottage in Winter Park, FL for your stay?
Cottages in Winter Park often offer a more unique and charming experience than a standard hotel. They are often located in quiet, residential areas, which can be a nice escape from the hustle and bustle of the city.
What are the best pet friendly cottage rentals in Winter Park, FL?
Can you easily explore Winter Park, FL on foot or by bike?
Winter Park is very walkable, especially the downtown area and Park Avenue. You can also rent a bike from one of the many shops in town and explore the city's many scenic trails and parks.
What are the best cottage rentals with parking in Winter Park, FL?
What are the best restaurants in Winter Park, FL with nature views?
The Lakeside Restaurant at the Alfond Inn offers stunning views of Lake Maitland. For a more casual dining experience, try The Porch, which has a beautiful patio overlooking the lake.
What family-friendly activities are available in Winter Park, FL?
The Winter Park Scenic Boat Tour is a great way to spend a day with the family. You can also visit the Central Florida Zoo & Botanical Gardens, which has a wide variety of animals and plants.
Destinations nearby
Best Winter Park, FL cottage rentals with jacuzzi
Among the 12 accommodations in Winter Park, FL, here are the 1 best cottage rentals with a jacuzzi
9.0 24 reviews
Winter Park, FL
11/08 – 13/08
$376/nighttotal: $752 (2 )
Garden Cottage-swim/spa Sleeps 6 Ctrl Orlando Disney Universal Seaworld Beaches,
2 2
cottage , Altamonte Springs
This Altamonte Springs holiday home is conveniently located less than 1.6km from Cranes Roost Park and Uptown Altamonte, offering easy access to shops and restaurants, and within 56km of Orlando International Airport (MCO) and Sanford Airport (SFB). Sleeping six, this two-bedroom, one-bathroom property boasts a king and two queen beds, a fully equipped kitchen with island seating, a private garden, swimming pool, jacuzzi, and parking; an additional one-bedroom apartment is available upon request.
Best pet friendly Winter Park, FL cottage rentals
Among the 12 accommodations in Winter Park, FL, here are the 3 best pet friendly cottage rentals
Winter Park, FL
03/07 – 31/07
$242/nighttotal: $6776 (28 )
Walkable Quiet Lakefront Retreat Near Downtown Orlando With Private Patio
1 2
cottage , Conway
This Conway cottage offers a convenient base, located 11 kilometres from Lake Eola Park and 13 kilometres from the Kia Centre, with easy access to Florida Mall and Universal Orlando Resort. This one-bedroom dwelling accommodates two guests and includes amenities such as internet, air conditioning, a dryer, and ironing facilities, with essential toiletries provided.
9.0 24 reviews
Winter Park, FL
11/08 – 13/08
$376/nighttotal: $752 (2 )
Garden Cottage-swim/spa Sleeps 6 Ctrl Orlando Disney Universal Seaworld Beaches,
2 2
cottage , Altamonte Springs
This Altamonte Springs holiday home is conveniently located less than 1.6km from Cranes Roost Park and Uptown Altamonte, offering easy access to shops and restaurants, and within 56km of Orlando International Airport (MCO) and Sanford Airport (SFB). Sleeping six, this two-bedroom, one-bathroom property boasts a king and two queen beds, a fully equipped kitchen with island seating, a private garden, swimming pool, jacuzzi, and parking; an additional one-bedroom apartment is available upon request.
9.8 37 reviews
Winter Park, FL
02/08 – 04/08
$381/nighttotal: $762 (2 )
The Coach House- Entire Home - 2 Bedroom/3 Bath Orlando Getaway!
2 6
cottage , Orlando
This charming cottage is situated in the College Park district of Orlando, just a 25-minute drive from Orlando International Airport and major theme parks like Disney, Universal, and The Outlets. It has received excellent user ratings, making it a popular choice for travellers seeking a comfortable and convenient stay. The two-bedroom, three-bathroom cottage offers 111 square metres of space, comfortably accommodating up to eight guests. Amenities include a fully equipped kitchen, a private garden, a terrace, high-speed internet, and a 52" HD TV with Roku, ensuring a relaxing and enjoyable stay for all.