Vacation Rentals in Winter Park, FL

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Winter Park, FL vacation rentals
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288 Vacation rentals and Airbnb in Winter Park, FL

Best family friendly Winter Park, FL vacation rentals

Among the 288 accommodations in Winter Park, FL, here are the 4 best family friendly rentals

Entire Condo At Ventura - Comfy, Quiet Oasis In The Heart Of Orlando - Winter Park, FL
9.8 13 reviews
Winter Park, FL
14/08 – 21/08
₹13245/nighttotal: ₹92715 (7 )

Entire Condo At Ventura - Comfy, Quiet Oasis In The Heart Of Orlando

2 2
apartment , Orlando
This two-bedroom apartment is situated in Ventura, a quiet neighbourhood in Orlando, just 10 kilometres from Orlando International Airport and 20 kilometres from the Disney Parks. It has received excellent reviews from previous guests.
The apartment is ideal for families or groups of up to six people. It features a fully equipped kitchen, air conditioning, a swimming pool, a terrace, and parking. You can also enjoy on-site amenities such as tennis and pickleball courts, and an 18-hole golf course.
Bonheur Ala Maison - Winter Park, FL
9.7 151 reviews
Winter Park, FL
28/07 – 01/08
₹31310/nighttotal: ₹125240 (4 )

Bonheur Ala Maison

3 2
apartment , Casselberry
This Casselberry apartment, conveniently located near numerous shops and parks, offers a fantastic base for exploring the area.
Sleeping up to six guests, this three-bedroom, two-bathroom property boasts a fully equipped modern kitchen, marble bathrooms, a private backyard with a swimming pool, hot tub, and BBQ grill, plus smart TVs and high-speed Wi-Fi throughout.
Charming Heated Pool Home In Altamonte Springs - Winter Park, FL
9.6 135 reviews
Winter Park, FL
10/07 – 18/07
₹20953/nighttotal: ₹167624 (8 )

Charming Heated Pool Home In Altamonte Springs

3 4
apartment , Altamonte Springs
This house is located in Altamonte Springs, just 5 kilometres from Altamonte Mall, Maitland Art Center, and Cranes Roost Park, making it easy to explore the area. Guests have consistently rated this property excellent for its location, cleanliness, and overall experience.
The property is a 3-bedroom, 2-bathroom house with a floor area of 153 square metres, comfortably accommodating up to 6 guests. This family-friendly home offers a range of amenities including a swimming pool, terrace, garden, and parking, as well as a fully equipped kitchen and air conditioning for a comfortable stay.
Foodie Lovers Walkable Mills50 - Sleeps 10 - Near Downtown & Airport - Winter Park, FL
10 2 reviews
Winter Park, FL
14/08 – 21/08
₹13629/nighttotal: ₹95403 (7 )

Foodie Lovers Walkable Mills50 - Sleeps 10 - Near Downtown & Airport

1 2
house , Orlando
This Mills50 holiday home in Orlando is conveniently located 2.2 km from downtown Orlando, 3.4 km from Church Street Station, and 4.2 km from the Amway Center, offering easy access to major attractions.
The 91 square metre property features one bedroom, one bathroom, sleeps ten guests, and includes a fully equipped kitchen, private patio, garden, free Wi-Fi, and a washing machine.

Best Winter Park, FL holiday rentals with parking

Cozy 2bd 2bth House Walk To Local Gems - Winter Park, FL
9.2 7 reviews
Winter Park, FL
10/07 – 18/07
₹17044/nighttotal: ₹136352 (8 )

Cozy 2bd 2bth House Walk To Local Gems

2 4
house , Orlando
This Orlando house, situated 2.6km from the city centre and within 8km of Church Street Station, Camping World Stadium, and the Kia Center, offers convenient access to major attractions.
This two-bedroom, two-bathroom property sleeps seven, boasting a fully equipped kitchen with dishwasher, a terrace, garden, free Wi-Fi, and free private parking; enjoy al fresco dining and proximity to local amenities.
Romantic Lakefront Getaway With Balcony Near Downtown Orlando - Winter Park, FL
Winter Park, FL
28/06 – 18/07
₹13982/nighttotal: ₹279640 (20 )

Romantic Lakefront Getaway With Balcony Near Downtown Orlando

1 1
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.
Renovated Luxury 6000 Sqft Mansion In Downtown Orlando Sleep 14 Near Theme Parks - Winter Park, FL
9.6 19 reviews
Winter Park, FL
28/06 – 18/07
₹129708/nighttotal: ₹2594160 (20 )

Renovated Luxury 6000 Sqft Mansion In Downtown Orlando Sleep 14 Near Theme Parks

6 1
apartment , Orlando
This six-bedroom Orlando holiday home is centrally located, within a 2.4km walk of Lake Eola and the Dr Phillips Center for the Performing Arts, and under 5km from Camping World Stadium and the Kia Forum.
The 557 square metre property boasts a private water park, on-site arcade, and sleeps up to 14 guests, offering a fully equipped kitchen, swimming pool, spa, and a relaxing garden with a living plant wall.
Traveler's Dream: Refresh & Recharge Poolside - Winter Park, FL
9.4 11 reviews
Winter Park, FL
28/07 – 01/08
₹10429/nighttotal: ₹41716 (4 )

Traveler's Dream: Refresh & Recharge Poolside

1 2
apartment , Casselberry
This Casselberry flat is conveniently located approximately 3.5 km from Secret Lake Park and 4.5 km from Red Bug Lake Park, offering easy access to outdoor recreation.
The one-bedroom, one-bathroom apartment sleeps two guests and features a private pool, free Wi-Fi, a fully equipped kitchen with fridge and microwave, a smart TV, and access to a community pool; Winter Park Village and Altamonte Mall are within a 10 km radius.

Frequently asked questions about holiday rentals in Winter Park, FL

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Best Winter Park, FL holiday rentals with a balcony

2 Bdrm Penthouse With Billiards - Winter Park, FL
9.9 9 reviews
Winter Park, FL
10/07 – 18/07
₹29986/nighttotal: ₹239888 (8 )

2 Bdrm Penthouse With Billiards

1 4
apartment , Orlando
This Orlando penthouse apartment is situated in the city centre, less than 0.6km from various attractions and 14km from Orlando International Airport.
The 150 square metre dwelling boasts two bedrooms, two bathrooms, a fully equipped kitchen, in-unit laundry, a billiards table, free Wi-Fi, and accommodates up to seven guests.
Charming Winter Park Fully Furnished & Pet Friendly Farmhouse Bungalow - Winter Park, FL
9.4 225 reviews
Winter Park, FL
14/08 – 21/08
₹13297/nighttotal: ₹93079 (7 )

Charming Winter Park Fully Furnished & Pet Friendly Farmhouse Bungalow

3 2
apartment , Goldenrod
This Goldenrod holiday home is located just 2.2 kilometres from Full Sail University, and within a 10-kilometre radius of the University of Central Florida, Albin Polasek Museum and Sculpture Gardens, Rollins College, and Kraft Azalea Gardens. The property has received excellent ratings for location, cleanliness and user experience.
The house has three bedrooms and two bathrooms, accommodating up to six guests. Amenities include a fully equipped kitchen with a fridge, microwave, and dishwasher, air conditioning, a terrace, a garden, parking, and internet access.
Spring Lake King Balcony Suite - Winter Park, FL
8.4 16 reviews
Winter Park, FL
28/07 – 01/08
₹15138/nighttotal: ₹60552 (4 )

Spring Lake King Balcony Suite

1 2
apartment , Conway
This pet-friendly Conway apartment, near Spring Lake, is situated approximately 3.5 kilometres from Conway's city centre and within 7-8 kilometres of the Amway Center, Camping World Stadium, and Orlando International Airport.
The 33-square-metre self-catering flat offers one bedroom, one bathroom, sleeps two guests, and includes a private balcony, garden, parking, Wi-Fi, and a kitchen with a dishwasher, microwave, and fridge.
Apartment ∙ 2 Bedrooms ∙ 4 Guests - Winter Park, FL
Winter Park, FL
10/07 – 18/07
₹14307/nighttotal: ₹114456 (8 )

Apartment ∙ 2 Bedrooms ∙ 4 Guests

2 4
apartment , Orlando
This Orlando flat is located within a secure resort community, 16 kilometres from the main theme parks and 8 kilometres from Orlando International Airport.
This two-bedroom, two-bathroom apartment sleeps four and offers resort-style amenities including a swimming pool, fitness centre, tennis, pickleball, and basketball courts, alongside a furnished patio and a fully equipped kitchen.

Best pet friendly Winter Park, FL vacation rentals

Among the 288 accommodations in Winter Park, FL, here are the 4 best pet friendly rentals

Cozy Apt With Pool, Hot Tub, Golf, Near Downtown - Winter Park, FL
Winter Park, FL
28/07 – 01/08
₹14295/nighttotal: ₹57180 (4 )

Cozy Apt With Pool, Hot Tub, Golf, Near Downtown

2 2
house , Orlando
This Orlando dwelling is situated 8.05 kilometres from Church Street Station and 8.19 kilometres from the Kia Centre, with Orlando International Airport a mere 8.05 kilometres away.
This 76 square metre holiday home accommodates up to seven guests and features a kitchen with a fridge, microwave, and dishwasher, air conditioning, a swimming pool, hot tub, balcony, garden, fitness centre, and tennis courts, with free Wi-Fi provided.
Drayton Place Staycation - Private Lk/pk Front Ste - Winter Park, FL
9.3 40 reviews
Winter Park, FL
10/07 – 18/07
₹22691/nighttotal: ₹181528 (8 )

Drayton Place Staycation - Private Lk/pk Front Ste

2 4
apartment , Orlando
This waterfront holiday home is located just 1.6 kilometres from the Kia Center, within a 10-minute walk of Camping World Stadium and Tinker Field. It has excellent user, location and cleanliness ratings.
The property offers two bedrooms and a bathroom, covering 42 square metres and accommodating up to four guests. It has a range of amenities including a swimming pool, spa, garden, terrace, and a fully equipped kitchen.
Cozy Golf Condo With 3 Pools, Gym And Just 15 Minutes To Airport - Winter Park, FL
Winter Park, FL
14/08 – 21/08
₹10678/nighttotal: ₹74746 (7 )

Cozy Golf Condo With 3 Pools, Gym And Just 15 Minutes To Airport

1 2
house , Orlando
This golf condo is situated approximately 8 kilometres from Orlando International Airport and within 12.4 kilometres of downtown Orlando attractions, including Church Street Station and the Kia Centre.
This property offers accommodation for up to seven guests, featuring a fully equipped kitchen with a dishwasher and oven, air conditioning, complimentary WiFi, access to three swimming pools, a fitness centre, a hot tub, and a garden, with a floor area of 63 square metres and one bathroom.
3bdrm Fruit Tree Home Near Downtown Orlando - Winter Park, FL
9.0 22 reviews
Winter Park, FL
28/06 – 18/07
₹20640/nighttotal: ₹412800 (20 )

3bdrm Fruit Tree Home Near Downtown Orlando

3 1
apartment , Orlando
This Orlando home is located just 1.1 km from Grand Avenue Park and within 5 km of Kia Center and Camping World Stadium, making it a convenient base for exploring the city's attractions. It has received excellent user ratings, so you can be sure of a comfortable stay.
The property has 3 bedrooms and can accommodate up to 8 guests, making it suitable for families or groups of friends. The house offers a range of amenities, including a swimming pool, jacuzzi, garden, and free Wi-Fi, ensuring a relaxing and enjoyable stay.
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