Holiday Rentals in Winter Park, FL

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

Best family friendly Winter Park, FL holiday rentals

Among the 405 accommodations in Winter Park, FL, here are the 4 best family friendly rentals

Historic Orlando Casita Love, Lake Eola, Delaney Park, 2 Bedrooms 1 Bathroom - Winter Park, FL
8.4 12 reviews

Historic Orlando Casita Love, Lake Eola, Delaney Park, 2 Bedrooms 1 Bathroom

apartment, Orlando
This renovated Casita, located in downtown Orlando near Lake Eola and Delaney Park, is a 12-minute walk from Church Street Station and within 1.3 km of the Amway Center and 4 km of Camping World Stadium.
This 2-bedroom, 1-bathroom apartment offers 300 square metres of space, sleeps up to 7 guests, and includes free Wi-Fi, private parking, a fully equipped kitchen, and air conditioning.
Winter Park Oasis - Winter Park, FL
9.6 27 reviews

Winter Park Oasis

apartment, Winter Park
This two-bedroom house is located in Winter Park, just 2 kilometres from Kraft Azalea Gardens and Winter Park Village, offering easy access to shops, restaurants and cultural attractions. The house has received excellent user ratings, indicating a high level of satisfaction from previous guests.
The house can comfortably accommodate up to 4 guests and features a fully equipped kitchen, a garden, a patio and air conditioning. Guests can enjoy free Wi-Fi, a terrace and parking, making it an ideal choice for families or groups of friends looking for a relaxing and comfortable stay.
Orlando Oasis! Free Laundry & Parking Near Disney! - Winter Park, FL
9.2 42 reviews

Orlando Oasis! Free Laundry & Parking Near Disney!

house, Orlando
This Orlando holiday home is located just 4.5km from Church Street Station and 4.7km from Amway Center, offering easy access to the city's main attractions. It has received excellent ratings for location, cleanliness, and overall experience.
The property has three bedrooms, one bathroom, and spans 102 square metres, comfortably accommodating up to eight guests. Guests can enjoy modern amenities including air conditioning, free Wi-Fi, a fully equipped kitchen, and a garden with an outdoor fireplace and barbecue facilities.
Orlando Poolside Oasis - Winter Park, FL
9.9 111 reviews

Orlando Poolside Oasis

house, Altamonte Springs
This Altamonte Springs holiday home boasts a peaceful suburban setting, conveniently located within easy reach of Orlando's theme parks and Florida's beaches, though precise distances aren't provided.
Sleeping six guests, the three-bedroom, two-bathroom property offers a fully equipped kitchen with dishwasher, a private swimming pool, free Wi-Fi, and family-friendly amenities including a cot, stroller, and baby bath available on request.

Best Winter Park, FL holiday rentals with parking

3 Br Near Downtown| Hotub, Pool, Gazebo | Sleeps 7 - Winter Park, FL
9.5 66 reviews

3 Br Near Downtown| Hotub, Pool, Gazebo | Sleeps 7

apartment, Orlando
This three-bedroom, two-bathroom holiday home is situated near Orlando's Ivanhoe Village and Mills District, offering easy access (within 1.6km) to I-4, Dubsdread Golf Course, and AdventHealth, and approximately 17.7km from Downtown Orlando and the Dr. Phillips Center for the Performing Arts.
Sleeping up to eight guests, the property boasts a full kitchen, washer/dryer, high-speed Wi-Fi, a swimming pool, jacuzzi, and parking, plus a unique 'cowboy pool', all within a stylish interior featuring a neutral palette and turquoise accents.
Winter Park Oasis - Winter Park, FL
9.9 55 reviews

Winter Park Oasis

house, Winter Park
This Winter Park bungalow is ideally situated a short drive (approximately 3-5 km) from Park Avenue's restaurants, Rollins College, and downtown Orlando, with beaches also accessible within a reasonable driving distance.
The two-bedroom, one-bathroom property sleeps four guests and offers free Wi-Fi, parking for two cars, a garden, and a kitchen equipped with a fridge, freezer, and microwave; nearby local parks are easily accessible on foot or by car.
City Orlando Living! - Winter Park, FL
No reviews

City Orlando Living!

apartment, Orlando
This 3-bedroom, 2-bathroom flat is located in Orlando's North College Park district, within walking distance of grocery stores, restaurants, parks, and lakes, and a short drive from Winter Park, downtown Orlando, and the Disney theme parks.
This pet-friendly apartment offers air conditioning, internet, parking, and an in-unit LG washer and dryer, with guest capacity for 3 people, and is conveniently situated near The Mall at Millenia and Orlando Health.
The Clementine Boho Home In Orlandos Food Scene - Winter Park, FL
9.6 27 reviews

The Clementine Boho Home In Orlandos Food Scene

apartment, Orlando
This Orlando guest house, situated in the Park Lake – Highland neighbourhood, offers easy access to Winter Park and is within a 32- to 56-kilometre radius of major theme parks such as Universal Orlando Resort, SeaWorld Orlando, and Walt Disney World Resort.
The self-contained unit sleeps five, features a kitchen with a fridge and microwave, a private backyard, and access to a tennis court, parking, and outdoor amenities including a barbecue and trampoline; nearby attractions include the Central Florida Fairgrounds and Camping World Stadium.

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.

Popular destinations

Best Winter Park, FL holiday rentals with a balcony

6 Months Min - Winter Park, FL
9.0 4 reviews

6 Months Min

apartment, Wekiwa Springs
This Longwood condo offers a prime location with straightforward access to the I-4, placing you within easy reach of Casselberry Golf Club and numerous dining and shopping venues, all within 1 kilometre of your accommodation. This two-bedroom flat, accommodating up to four guests, boasts a fully remodelled interior with original European artwork, a well-equipped kitchen, smart TV with streaming services, and access to two communal swimming pools.
Landing Stunning 1bd Rooftop Lounge Gym - Winter Park, FL
No reviews

Landing Stunning 1bd Rooftop Lounge Gym

apartment, Orlando
Apartment listing. You will stay in Orlando.
Facilities and services include a terrace, an iron and a fridge. Enjoy a gym in this apartment in Orlando!
Landing | Chic 1bd, Rooftop Lounge, Gym - Winter Park, FL
No reviews

Landing | Chic 1bd, Rooftop Lounge, Gym

apartment, Orlando
This 52 square metre one-bedroom flat is located in Downtown Orlando, offering convenient access to Florida Mall and Orlando International Premium Outlets, and a short drive from Universal Orlando Resort.
This fully furnished apartment for two guests includes a dedicated workspace with fast WiFi, air conditioning, and a balcony, with access to luxury amenities such as a pool, hot tub, and fitness centre.
Modern Comfort: Mills/50 Hideaway - Winter Park, FL
8.4 5 reviews

Modern Comfort: Mills/50 Hideaway

apartment, Orlando
This Orlando apartment, situated in the Colonialtown North district, is less than 1.1 kilometres from Harry P. Leu Gardens and within 3.2 kilometres of the Plaza Theatre.
The one-bedroom flat sleeps two guests and includes a kitchen with fridge and microwave, a washing machine, a garden, parking, and internet access; nearby attractions include the Orlando Museum of Art.

Best pet friendly Winter Park, FL holiday rentals

Among the 405 accommodations in Winter Park, FL, here are the 4 best pet friendly rentals

Fashionable Location Netflix  Parking Wifi - Winter Park, FL
9.6 417 reviews

Fashionable Location Netflix Parking Wifi

apartment, Azalea Park
This two-bedroom apartment is situated in Azalea Park, just 15 kilometres from downtown Orlando, Amway Center, Winter Park, UCF, and the airport, making it a convenient base for exploring the area. The apartment has received excellent ratings for location, cleanliness, and overall user experience.
The apartment comfortably accommodates up to four guests, with a queen bed and two twin beds. Amenities include a fully equipped kitchen, free parking, air conditioning, internet access, and a security system.
Guest House Near Attractions - Winter Park, FL
9.6 289 reviews

Guest House Near Attractions

apartment, Altamonte Springs
This two-bedroom apartment is located in a quiet neighbourhood in Altamonte Springs, just 5-10 kilometres from the nearest shopping mall and within walking distance of the Sunrail train station. It has received excellent ratings for its cleanliness, location and user experience.
The apartment is fully furnished and equipped with a kitchen, living room, and a 65-inch TV, and can comfortably accommodate up to six guests. Guests can enjoy modern amenities such as granite countertops, ceramic floors, and Wi-Fi, and are also within easy reach of downtown Orlando, Disney attractions, and beaches.
Floyd - Luxury 2br W/ Rooftop Pool, Gym, Balcony - Winter Park, FL
10 1 review

Floyd - Luxury 2br W/ Rooftop Pool, Gym, Balcony

apartment, Orlando
This modern luxury condominium in Orlando offers excellent city views and is centrally located, placing you within a 1.6 to 2.4 kilometre drive of the Amway Centre, Downtown Orlando, International Drive, and the Orlando Convention Centre, with Disneyworld and Universal Studios also within easy reach. This two-bedroom, two-bathroom flat accommodates up to five guests and features a fully equipped kitchen, high-speed Wi-Fi, air conditioning, and access to building amenities such as a rooftop swimming pool and fitness centre, with pets permitted.
2 Mi To Dt Orlando & Winter Park - Winter Park, FL
8.0 7 reviews

2 Mi To Dt Orlando & Winter Park

house, Orlando
This Orlando holiday home is situated near Downtown Orlando and Winter Park, less than 3.2 kilometres from Church Street Station and within a 5.5-kilometre radius of the Amway Center and Camping World Stadium.
The 67-square-metre property offers two bedrooms, one bathroom, sleeps seven guests, and includes a fully equipped kitchen, air conditioning, Wi-Fi, in-unit laundry, and a private patio; Universal Studios Florida and Islands of Adventure are also within easy reach.
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