Compare Vacation Rentals & Airbnb in Winter Park, FL

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Winter Park, FL vacation rentals
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288 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

Salt Pool, Cozy House Near Downtown And International Airport - Winter Park, FL
9.6 99 reviews
Winter Park, FL
08/01 – 29/01
$245/nighttotal: $5145 (21 )

Salt Pool, Cozy House Near Downtown And International Airport

3 2
apartment , Orlando
This three-bedroom apartment is located in Dixie Belle, a neighbourhood in Orlando, just 10 kilometres from the city centre and 10 kilometres from Orlando International Airport. The property has excellent user ratings and is highly recommended for families and groups.
The apartment has a split floorplan with its own private access to the outdoor pool, providing a sense of seclusion. It comfortably sleeps six guests and features a fully equipped kitchen, a family living room, a private backyard with a pool, a brand-new grill, and a spa.
Luxury 6000 Sqft Mansion In Downtown Orlando Sleeps 12 - Winter Park, FL
8.3 4 reviews
Winter Park, FL
28/06 – 18/07
$2979/nighttotal: $59580 (20 )

Luxury 6000 Sqft Mansion In Downtown Orlando Sleeps 12

6 1
house , Orlando
This luxurious six-bedroom villa is situated in Downtown Orlando, Florida, 1.8km from Church Street Station and 2.3km from the Amway Center.
The 560 square metre property boasts five bathrooms, sleeps 23 guests, and includes a private pool table, free Wi-Fi, and a fully equipped kitchen; nearby attractions include Camping World Stadium and the Florida Mall.
Roy's Guest House - Winter Park, FL
9.9 99 reviews
Winter Park, FL
03/09 – 08/09
$187/nighttotal: $935 (5 )

Roy's Guest House

1 2
house , Orlando
Roy's guest house offers a private, quiet retreat in Orlando, Florida, conveniently located 5km from Church Street Station, 6km from the Amway Center, and 7.6km from Camping World Stadium.
This self-catering property boasts a 39 square metre floor area with one bedroom, one bathroom, sleeping up to three guests, and features a fully equipped kitchen, free Wi-Fi, and a private garden.
213 Winter Park/downtown Villa+studio Pri Entrance - Winter Park, FL
9.7 123 reviews
Winter Park, FL
10/07 – 18/07
$284/nighttotal: $2272 (8 )

213 Winter Park/downtown Villa+studio Pri Entrance

1 4
apartment , Fern Park
This Fern Park studio apartment, near the Kissimmee border, offers easy access to major Orlando attractions; Universal Studios is 24 minutes (approx. 38.6km), Disney World 30 minutes (approx. 48.3km), SeaWorld 29 minutes (approx. 46.7km), and Winter Park 15 minutes (approx. 24.1km) away.
Sleeping up to 14 guests, this five-bedroom, three-bathroom self-catering property boasts a fully equipped kitchen, Jacuzzi, garden, high-speed internet (300 Mbps), and free parking; a children's play structure is also available in the large, fenced backyard.

Best Winter Park, FL vacation rentals with parking

House Close To Downtown Orlando Has Walking Trail And Next To Baldwin Park Lake - Winter Park, FL
9.8 27 reviews
Winter Park, FL
08/01 – 29/01
$226/nighttotal: $4746 (21 )

House Close To Downtown Orlando Has Walking Trail And Next To Baldwin Park Lake

4 2
apartment , Orlando
This three-bedroom, two-and-a-half-bathroom townhouse is situated in Baldwin Park, Orlando, a short 19-24 km drive from Downtown Orlando and within a 48 km radius of Walt Disney World Resort, Universal Orlando Resort, and SeaWorld Orlando.
The fully remodelled property sleeps six guests and offers a kitchen with fridge, microwave, and dishwasher, plus air conditioning, parking, and Wi-Fi; nearby amenities include Baldwin Lake, with its walking and cycling trails.
Home In Orlando - Winter Park, FL
9.6 8 reviews
Winter Park, FL
10/07 – 18/07
$279/nighttotal: $2232 (8 )

Home In Orlando

3 4
apartment , Azalea Park
This three-bedroom apartment in Orlando's Azalea Park neighbourhood offers convenient access to major attractions such as Universal Orlando Resort and the Wizarding World of Harry Potterâ„¢, with distances to these locations not specified in the property description.
The self-catering property sleeps six guests across three bedrooms (one king, two queen beds) and two bathrooms (each with a bath and shower), and includes air conditioning, Wi-Fi, and a washing machine; nearby amenities include the Florida Mall and Orlando International Premium Outlets.
Galaxy By Airport, Downtown, 408/417 , Theme Park - Winter Park, FL
10 1 review
Winter Park, FL
03/07 – 31/07
$120/nighttotal: $3360 (28 )

Galaxy By Airport, Downtown, 408/417 , Theme Park

1 2
apartment , Azalea Park
This one-bedroom flat in Azalea Park, Orlando, offers convenient access to the Kia Centre, located 7.8 kilometres away, and the Florida Mall, situated 16.9 kilometres from the property.
This apartment provides a fridge, microwave, air conditioning, Wi-Fi, and on-site parking for up to four guests, with a nearby laundromat available.
Cute & Cozy Guest Suite In Orlando Near Disney, Universal, Downtown, And Airport - Winter Park, FL
Winter Park, FL
03/07 – 31/07
$113/nighttotal: $3164 (28 )

Cute & Cozy Guest Suite In Orlando Near Disney, Universal, Downtown, And Airport

1 2
apartment , Conway
This private studio apartment in Conway is situated near the Sodo and Hourglass Districts, offering convenient access to Orlando International Airport (24 km), Disney (40 km), Universal Studios (32 km), and Downtown Orlando (24 km).
This soundproofed suite accommodates up to four guests and features air conditioning, internet, and parking, making it an ideal base for exploring nearby attractions such as Universal Orlando Resort and Florida Mall.

Frequently Asked Questions about vacation rentals in Winter Park, FL

  • What should a first-time visitor not miss in Winter Park, FL?

    Winter Park is a charming city! For a first-timer, you definitely shouldn't miss the scenic beauty of the Central Park, a beautiful green space in the heart of Winter Park, and the iconic Rollins College, a historic college campus with beautiful architecture. Also, take a stroll down Park Avenue, a vibrant street with shops, restaurants, and art galleries.
  • What are the best Airbnb and vacation rentals in Winter Park, FL?

    Upscale Loft Space Close To Downtown, Downtown Lake Eola Historic House 1 Or 2 Bed and Moniker Manor (Entire Home Near Downtown) are the most popular Airbnb and vacation rentals in Winter Park, FL among travelers.

  • Which neighborhood in Winter Park, FL should you consider for a vacation rental?

    The best neighbourhood for a vacation rental really depends on your preferences. If you want to be close to the action, consider staying in the Winter Park Village, close to shops and restaurants. For a more residential feel, Baldwin Park is a great choice, known for its beautiful homes and parks. If you want a quieter experience, Lake Howell is a good option, with its peaceful lakeside setting.
  • What are the most popular Airbnbs in Winter Park, FL?

  • What are the top family-friendly attractions in Winter Park, FL?

    Winter Park is a great place for families! The Charles Hosmer Morse Museum of American Art is a great place to explore with kids, featuring a collection of Tiffany glass. For a fun day out, the Winter Park Scenic Boat Tour is a great way to see the city from the water. And don't forget the Central Park, with its playgrounds and open spaces, perfect for a picnic.
  • What are the best vacation rentals with a pool in Winter Park, FL?

  • When is the best time to book a vacation rental in Winter Park, FL?

    The best time to book a vacation rental in Winter Park really depends on your preferences. Peak season is from December to April, when the weather is mild and sunny, so expect higher prices. If you're looking for a better deal, consider visiting during the shoulder seasons, May to June or September to November, when the weather is still pleasant but the crowds are smaller.
  • What are the best rentals for families and kids in Winter Park, FL?

  • What events or festivals should visitors check out in and around Winter Park, FL?

    Winter Park has a lively events calendar. The Winter Park Sidewalk Art Festival is a must-see for art lovers, held in March. The Winter Park Autumn Art Festival, held in October, is another great option for art enthusiasts. For a festive experience, the Winter Park Christmas in the Park is a magical event held in December.
  • What are the best rentals or Airbnbs with a jacuzzi in Winter Park, FL?

  • What are the best budget-friendly activities in Winter Park, FL?

    Winter Park has plenty of budget-friendly activities. A stroll through the Central Park is a great way to enjoy the outdoors without spending a penny. For a unique experience, visit the Albin Polasek Museum & Sculpture Gardens, a beautiful museum and garden with free admission on the first Saturday of every month. The Winter Park Farmers Market is a great place to find local produce and crafts at affordable prices.
  • What are the best restaurants with local dishes in Winter Park, FL?

    For a taste of local cuisine, The Wine Room is a great spot, known for its Florida-inspired dishes. Bosphorous is another popular choice, serving authentic Turkish cuisine. If you're looking for a more casual dining experience, The Porch is a great option, with a menu featuring fresh, seasonal dishes.
  • What are the best walking or cycling routes in Winter Park, FL?

    Winter Park is a very walkable city. For a scenic walk, try the Winter Park Trail, a paved trail that runs along the shores of Lake Maitland. For a longer ride, the Cady Way Trail is a great option, a 12 km paved trail that stretches through the city.
  • Are there pet-friendly attractions in Winter Park, FL?

    Winter Park is a very dog-friendly city. The Central Park is a great place to let your furry friend run around. The Winter Park Scenic Boat Tour also welcomes well-behaved dogs on board. Many restaurants and shops in Winter Park are also pet-friendly.
  • What are the benefits of choosing a vacation rental in Winter Park, FL?

    Vacation rentals in Winter Park offer a more spacious and comfortable option compared to hotels. They often include amenities like a kitchen and laundry facilities, which can be very convenient for families or groups. Vacation rentals also offer more privacy and flexibility, allowing you to come and go as you please.
  • What are the top sports attractions and facilities in Winter Park, FL?

    Winter Park has a variety of sports attractions and facilities. The Winter Park Racquet Club is a popular spot for tennis enthusiasts. The Winter Park Golf Course is a beautiful 18-hole course. For a more casual experience, there are also several parks with basketball courts, volleyball courts, and playgrounds.

Destinations nearby

Best Winter Park, FL vacation rentals with a balcony

2 Bdrm Penthouse With Billiards - Winter Park, FL
9.9 9 reviews
Winter Park, FL
10/07 – 18/07
$439/nighttotal: $3512 (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.
Brand New Luxury Modern 5br/4.5ba+game Room Home - Winter Park, FL
10 6 reviews
Winter Park, FL
10/07 – 18/07
$708/nighttotal: $5664 (8 )

Brand New Luxury Modern 5br/4.5ba+game Room Home

5 4
apartment , Altamonte Springs
This Altamonte Springs flat is situated 39 kilometres from the Magic Kingdom and 29 kilometres from Universal Studios Florida, offering convenient access to major Orlando theme parks.
This spacious 307 square metre residence features five bedrooms, four bathrooms, and accommodates up to 15 guests with amenities including a fully equipped kitchen, a dedicated game room, and ample parking.
2-bedroom 2 Bath Bungalow In Peaceful Orlando With Ac For Relaxing Stays - Winter Park, FL
Winter Park, FL
03/07 – 10/07
$204/nighttotal: $1428 (7 )

2-bedroom 2 Bath Bungalow In Peaceful Orlando With Ac For Relaxing Stays

2 2
apartment , Azalea Park
This two-bedroom, two-bathroom flat is located in the Azalea Park district of Orlando, offering easy access to Florida Mall and Orlando International Premium Outlets, and is approximately 13 kilometres from Orlando International Airport.
This pet-friendly accommodation sleeps up to five guests and includes air conditioning, a jacuzzi, a terrace, and a kitchen equipped with a microwave and dishwasher, with parking also provided.
New Construction Home, 3 Blocks S Downtown Orlando, In Lake Davis Neighborhood - Winter Park, FL
10 2 reviews
Winter Park, FL
03/07 – 10/07
$347/nighttotal: $2429 (7 )

New Construction Home, 3 Blocks S Downtown Orlando, In Lake Davis Neighborhood

2 2
apartment , Orlando
This 2-bedroom flat in Orlando's Lake Davis district is situated three blocks south of the city centre, offering proximity to Lake Eola (0.8 km), Orlando Health Hospital (1.3 km), Dr. Phillips Centre (1.1 km), and the Kia Centre (1.8 km), with Disney and Universal Studios within 25 km.
This accommodation for four guests features a full kitchen with high-end appliances including a convection oven and induction stovetop, a master bedroom with a king-size bed, a soaking tub in the bathroom, and a 2.4 x 4.8 metre balcony, alongside amenities such as a 75-inch QLED television and in-room Alexa music.

Best pet friendly Winter Park, FL vacation rentals

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

15 Min Away From - Universal Studios! -Cozy Studio - Winter Park, FL
Winter Park, FL
03/07 – 10/07
$150/nighttotal: $1050 (7 )

15 Min Away From - Universal Studios! -Cozy Studio

1 2
studio , Orlando
This Orlando apartment is situated centrally, just an 8-minute drive from the Dr. Phillips Centre for the Performing Arts and the Kia Centre, with Universal's Epic Universe approximately 13.7 kilometres away and Disney 48.3 kilometres away.
This pet-friendly studio apartment accommodates two guests and features air conditioning, complimentary WiFi in a private courtyard, and free parking, with coffee and tea provided.
Beautiful Downtown Condo 1 Bed 1 Bath - Winter Park, FL
10 2 reviews
Winter Park, FL
08/01 – 29/01
$248/nighttotal: $5208 (21 )

Beautiful Downtown Condo 1 Bed 1 Bath

1 2
house , Orlando
This Orlando city centre apartment is located 0.6km from the city centre, a 14-minute walk from Church Street Station, and a short drive from Camping World Stadium and the Holy Land Experience.
The 110 square metre property features one bedroom, one bathroom, sleeps three guests, and includes a fully equipped kitchen with dishwasher, private balcony, in-unit laundry, and free Wi-Fi.
Modern 3br | Walk To Restaurants, Bars & Publix - Winter Park, FL
9.9 33 reviews
Winter Park, FL
10/07 – 18/07
$221/nighttotal: $1768 (8 )

Modern 3br | Walk To Restaurants, Bars & Publix

1 4
apartment , Orlando
This Orlando apartment rental is situated in the Mills 50 district, a short drive (approx. 32km) from Walt Disney World and 16km from Universal Studios Florida, offering easy access to Kadence, a Michelin-starred restaurant, and a Publix supermarket.
The three-bedroom, two-and-a-half-bathroom property sleeps eight guests, features a fully equipped kitchen, private backyard with BBQ, and a dedicated workspace; enjoy nearby bars and restaurants, plus Lake Eola Park (approx. 10km).
Charming Heated Pool Home In Altamonte Springs - Winter Park, FL
9.6 135 reviews
Winter Park, FL
28/06 – 18/07
$325/nighttotal: $6500 (20 )

Charming Heated Pool Home In Altamonte Springs

3 1
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.
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