Holiday Rentals in Winter Park, FL

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Winter Park, FL holiday rentals
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288 Holiday rentals and Airbnb in Winter Park, FL

Best family friendly Winter Park, FL holiday rentals

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

Roy's Guest House - Winter Park, FL
9.9 99 reviews
Winter Park, FL
28/07 – 01/08
109 â‚¬/nighttotal: 436 â‚¬ (4 )

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.
Tiny House In Orlando - Winter Park, FL
8.8 11 reviews
Winter Park, FL
14/08 – 21/08
67 â‚¬/nighttotal: 469 â‚¬ (7 )

Tiny House In Orlando

1 2
apartment , Maitland
This Lockhart apartment, a self-contained flat ideal for solo travellers, is unfortunately lacking precise location details, preventing specification of proximity to local landmarks.
The 1-bedroom, 1-bathroom unit offers air conditioning, Wi-Fi, linens, towels, and basic toiletries; further details regarding size, layout, and nearby attractions are unavailable.
Spacious Central Florida Home Family Friendly! - Winter Park, FL
9.5 66 reviews
Winter Park, FL
10/07 – 18/07
230 â‚¬/nighttotal: 1840 â‚¬ (8 )

Spacious Central Florida Home Family Friendly!

4 4
house , Wekiwa Springs
This house is situated in Orlando, 19 kilometres from Camping World Stadium, 21 kilometres from Church Street Station, and 24 kilometres from the Orlando area, offering a peaceful escape from the city's buzz while remaining conveniently close to its attractions. It receives consistently excellent ratings for location, cleanliness, and user experience, ensuring a comfortable and enjoyable stay.
The property spans 297 square metres and comfortably accommodates up to eight guests across its four bedrooms. Guests can enjoy a range of amenities, including a fully equipped kitchen, a garden, a spa, a fitness centre, and a Jacuzzi, making it ideal for families or groups looking for a relaxing and well-equipped holiday home.
Quiet Retreat 15 Minutes From Downtown Orlando, Orlando Airport International! - Winter Park, FL
9.6 25 reviews
Winter Park, FL
10/07 – 18/07
219 â‚¬/nighttotal: 1752 â‚¬ (8 )

Quiet Retreat 15 Minutes From Downtown Orlando, Orlando Airport International!

3 4
apartment , Azalea Park
Golden Cove Rental is situated in Azalea Park, a peaceful residential neighbourhood in Orlando, just 15km from Orlando International Airport, Interstate 4, and the city centre. This apartment has received very good user ratings, making it a popular choice for travellers.
This three-bedroom, two-bathroom property can accommodate up to 10 guests, making it ideal for families or groups. The apartment offers a range of amenities, including a fully equipped kitchen, air conditioning, a garden, a tennis court, and parking.

Best Winter Park, FL holiday rentals with parking

Cute & Cozy Guest Suite In Orlando Near Disney, Universal, Downtown, And Airport - Winter Park, FL
Winter Park, FL
28/06 – 18/07
74 â‚¬/nighttotal: 1480 â‚¬ (20 )

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

1 1
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.
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
120 â‚¬/nighttotal: 840 â‚¬ (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.
Spacious Orlando Retreat W/ Backyard Oasis  Near Downtown & Attractions - Winter Park, FL
9.0 4 reviews
Winter Park, FL
10/07 – 18/07
166 â‚¬/nighttotal: 1328 â‚¬ (8 )

Spacious Orlando Retreat W/ Backyard Oasis Near Downtown & Attractions

2 4
apartment , Fairview Shores
This two-bedroom flat in Orlando's Fairview Shores district provides a peaceful base, situated just a short drive from Walt Disney World Resort, Universal Studios & Islands of Adventure, and Downtown Orlando's entertainment and healthcare facilities.
This accommodation for up to five guests includes a microwave oven, dishwasher, air conditioning, and parking, with a private backyard and the allowance of pets, making it suitable for families and professionals alike.
The Emerald | Walk To Downtown Orlando & Lake Eola - Winter Park, FL
9.9 122 reviews
Winter Park, FL
28/06 – 18/07
120 â‚¬/nighttotal: 2400 â‚¬ (20 )

The Emerald | Walk To Downtown Orlando & Lake Eola

2 1
apartment , Orlando
This charming apartment is located in Downtown Orlando, just 15 kilometres from Universal Studios and the airport. It has received excellent ratings for cleanliness, location, and user experience.
The apartment, which can comfortably accommodate four guests, features a spacious living area and a well-equipped kitchen. It also offers amenities such as a private entrance, on-site parking, and a rainforest shower, making it a perfect choice for those looking for a comfortable and convenient stay in Orlando.

Frequently asked questions about holiday rentals in Winter Park, FL

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

    Families love the Central Park, with its playground and splash pad, and the Albin Polasek Museum & Sculpture Gardens, which has a great kids' area. The Charles Hosmer Morse Museum of American Art also has some engaging exhibits for families.
  • What are the best Airbnb and holiday rentals in Winter Park, FL?

    Modern Tropical Pool Home , Upscale Loft Space Close To Downtown and Moniker Manor (Entire Home Near Downtown) are among the best Airbnb and holiday rentals 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 is usually during the shoulder seasons, from September to November and March to May, to avoid the peak crowds and high prices of the winter holidays and summer months.
  • What are the most popular Airbnbs in Winter Park, FL?

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

    For a budget-friendly day out, you can explore the Winter Park Chain of Lakes by renting a kayak or canoe. The Kraft Azalea Garden is another great option, offering beautiful scenery and a peaceful atmosphere.
  • What are the best holiday rentals with a pool in Winter Park, FL?

  • What are the best restaurants with local dishes in Winter Park, FL?

    For a taste of local cuisine, try The Wine Room, which serves up delicious dishes made with fresh, seasonal ingredients. The Dixie Dharma Kitchen offers a unique blend of Southern and Asian flavours.
  • What are the best rentals for families and kids in Winter Park, FL?

  • What are the best walking or cycling routes in Winter Park, FL?

    The Winter Park Scenic Loop is a popular walking and cycling route, taking you past the Winter Park Chain of Lakes and through charming residential areas. The West Orange Trail is another great option for cyclists, offering a longer, more scenic ride.
  • What are the best rentals or Airbnbs with a jacuzzi in Winter Park, FL?

  • Are there pet-friendly attractions in Winter Park, FL?

    Yes, many attractions in Winter Park are pet-friendly. The Kraft Azalea Garden welcomes well-behaved dogs on leash. The Winter Park Chain of Lakes is also a great spot for a walk with your furry friend.
  • What are the benefits of choosing a vacation rental in Winter Park, FL?

    Vacation rentals offer more space and privacy compared to hotels. You can often find rentals with unique features like a private pool or a garden, and they can be a more affordable option for families or groups.
  • What are the top sports attractions and facilities in Winter Park, FL?

    Winter Park is home to the Winter Park Racquet Club, a popular destination for tennis enthusiasts. The Winter Park Golf Course is another great option for golfers, offering a challenging and scenic experience.

Destinations nearby

Best Winter Park, FL holiday rentals with a balcony

349 M² Casa ∙ 8 Quartos ∙ 24 Hóspedes - Winter Park, FL
Winter Park, FL
14/08 – 21/08
359 â‚¬/nighttotal: 2513 â‚¬ (7 )

349 M² Casa ∙ 8 Quartos ∙ 24 Hóspedes

8 2
house , Orlando
This expansive 8-bedroom villa in Storey Lake, Kissimmee, offers a prime location just 6.4 kilometres from Walt Disney World and minutes from Universal Studios, SeaWorld, and premier golf courses.
This property boasts a generous 349 square metre floor area, accommodating up to 24 guests with a private screened pool, spa, and a dedicated games room featuring Foosball, Air Hockey, and an NBA Game Machine.
*Travel Themed Property With Backyard Oasis* - Winter Park, FL
9.8 38 reviews
Winter Park, FL
10/07 – 18/07
444 â‚¬/nighttotal: 3552 â‚¬ (8 )

*Travel Themed Property With Backyard Oasis*

6 4
apartment , Casselberry
This six-bedroom apartment is located in Maitland, a suburb of Orlando, just 15 kilometres from Casselberry and within walking distance of a Walmart Supercenter and various restaurants. The apartment is rated excellent by previous guests and offers a comfortable and convenient base for exploring the many attractions of Orlando.
The apartment spans 232 square metres and comfortably accommodates up to 14 guests. It features a private pool, an outdoor kitchen, a fire pit, a game room, a travel-themed design, and a separate one-bedroom "Castaway Island" apartment.
Modern Getaway  Close To Disney - Winter Park, FL
Winter Park, FL
14/08 – 21/08
145 â‚¬/nighttotal: 1015 â‚¬ (7 )

Modern Getaway Close To Disney

1 2
apartment , Orlando
This Orlando flat offers easy access to Walt Disney World and Universal Orlando Resort, being just a short drive away, and is also conveniently located approximately 3 kilometres from The Mall at Millenia and Florida Mall.
This residence accommodates up to eight guests and features a fully equipped kitchen, in-home laundry, air conditioning, Wi-Fi, a private backyard, and parking, providing a comfortable base for exploring local attractions like the Kia Centre and Camping World Stadium.
Brand New Luxury Modern 5br/4.5ba+game Room Home - Winter Park, FL
10 6 reviews
Winter Park, FL
10/07 – 18/07
438 â‚¬/nighttotal: 3504 â‚¬ (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.

Best pet friendly Winter Park, FL holiday rentals

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

Cozy 2bd 2bth House Walk To Local Gems - Winter Park, FL
9.2 7 reviews
Winter Park, FL
10/07 – 18/07
154 â‚¬/nighttotal: 1232 â‚¬ (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.
15 Min Away From - Universal Studios! -Cozy Studio - Winter Park, FL
Winter Park, FL
14/08 – 21/08
97 â‚¬/nighttotal: 679 â‚¬ (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.
The Princeton- College Park’s Best Kept Secret! - Winter Park, FL
10 90 reviews
Winter Park, FL
10/07 – 18/07
153 â‚¬/nighttotal: 1224 â‚¬ (8 )

The Princeton- College Park’s Best Kept Secret!

2 4
bungalow , Orlando
This charming bungalow is situated in College Park, a peaceful neighbourhood just 16km from downtown Orlando and 37km from the theme parks. The property has consistently received excellent reviews for its location, cleanliness and overall experience.
The home offers a comfortable living space for up to 5 guests, with a fully equipped kitchen and a spacious living area. You'll find everything you need for a relaxing stay, including a large TV with Netflix, high-speed Wi-Fi, a washing machine and dryer, and complimentary hot beverages.
Fireplace And Lake View Just 10 Minutes To Downtown Near Parks - Winter Park, FL
8.0 1 review
Winter Park, FL
28/07 – 01/08
130 â‚¬/nighttotal: 520 â‚¬ (4 )

Fireplace And Lake View Just 10 Minutes To Downtown Near Parks

2 2
house , Conway
This Orlando holiday home in Conway is located 9.3 kilometres from Church Street Station and 10.5 kilometres from Camping World Stadium, placing it 10 minutes from downtown Orlando attractions and 6.9 kilometres from Orlando International Airport.
This 102 square metre cottage accommodates up to 7 guests across 2 bedrooms and 2 bathrooms, featuring a well-equipped kitchen with a fridge, microwave, and dishwasher, air conditioning, a garden, and Wi-Fi.
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