Compare Vacation Rentals & Airbnb in Winter Park, FL

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Winter Park, FL vacation rentals
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405 Rentals and Airbnb in Winter Park, FL

Best family friendly Winter Park, FL vacation rentals

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

Newly Remodeled Cottage - Winter Park, FL
10 2 reviews

Newly Remodeled Cottage

apartment, Winter Park
This newly remodelled two-bedroom flat is situated in Winter Park, Florida, a short 800-metre walk from Park Avenue's shops and restaurants.
This property accommodates up to four guests and features a modernised eat-in kitchen, a dedicated laundry room with a washer and dryer, and a screened rear porch with outdoor dining for three, making it ideal for families and pet owners.
Suites By The Wellborn - Winter Park, FL
8.8 74 reviews

Suites By The Wellborn

apartment, Orlando
Apartment with an excellent rating of 88% based on 74 reviews. Your accommodation will be based in Orlando.
Services and facilities: a wheelchair friendly access, a room service and free parking.
Great Central Location - Winter Park, FL
8.0 1 review

Great Central Location

house, Orlando
This holiday let is located 2.6 kilometres from central Orlando, 5.5 kilometres from the Kia Centre and 7.4 kilometres from Camping World Stadium.
This 60 square metre holiday home offers accommodation for up to 7 guests with air conditioning, Wi-Fi, a fully equipped kitchen, and a private terrace, with pets welcome.
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.

Best Winter Park, FL vacation rentals with parking

Peaceful Home Near Lake, Mins From Dwntwn Orlando - Winter Park, FL
10 10 reviews

Peaceful Home Near Lake, Mins From Dwntwn Orlando

apartment, Orlando
This Baldwin Park flat offers a prime Orlando location, just 1.6 to 2.4 kilometres from Downtown Orlando's attractions and a short drive to Walt Disney World and Universal Studios.
This one-bedroom flat accommodates four guests and features a swimming pool, fitness centre, and a garden, with a kitchen equipped with a microwave oven and dishwasher.
Brand New Luxury Modern 5br/4.5ba+game Room Home - Winter Park, FL
10 4 reviews

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

apartment, Altamonte Springs
This Altamonte Springs residence is situated 38.6 kilometres from the Disney Parks and 29 kilometres from Universal Studios, offering convenient access to major attractions.
This five-bedroom, four-bathroom holiday home accommodates up to 15 guests, featuring a fully equipped kitchen, Smart TVs in all rooms, a game room, and on-site parking.
Stylish Orlando Studio  2 Queens, Fast Wifi, Private Patio, Near Disney Parks!! - Winter Park, FL
No reviews

Stylish Orlando Studio 2 Queens, Fast Wifi, Private Patio, Near Disney Parks!!

studio, Orlando
This studio apartment is located in a quiet Orlando neighbourhood, offering quick access to the city centre and major theme parks, including Universal Studios Florida, and is just 1.6 kilometres from the Orlando International Premium Outlets.
The accommodation provides free 300 Mbps Wi-Fi, a kitchenette with a microwave and fridge, and a private patio, comfortably sleeping up to three guests with two queen beds and a dedicated workspace.
Funky Remodeled Otown Bungalow Sleeps 8 - Winter Park, FL
9.7 160 reviews

Funky Remodeled Otown Bungalow Sleeps 8

apartment, Winter Park
This Winter Park bungalow, ideally situated near Orlando, offers easy access to numerous attractions and is within convenient driving distance of major theme parks.
Sleeping up to eight guests, this two-bedroom, two-bathroom property boasts a well-equipped kitchen, multiple 55" Roku TVs, a dedicated workstation, and outdoor gazebo access.

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.

Popular destinations

Best Winter Park, FL vacation rentals with a balcony

Newly Remodeled Cottage - Winter Park, FL
No reviews

Newly Remodeled Cottage

apartment, Winter Park
This Winter Park flat is located in Hannibal Square, adjacent to a golf course and a short drive from Universal Studios Florida, Universal Orlando Resort, and Universal's Islands of Adventure.
This 84 square meter residence offers two bedrooms, sleeps up to four guests, and features a screened-in back porch with outdoor dining, a newly remodelled bathroom with a walk-in shower, and an eat-in kitchen.
The Blue Bungalow Peaceful | Porch | Hottub I Dt - Winter Park, FL
10 9 reviews

The Blue Bungalow Peaceful | Porch | Hottub I Dt

apartment, Orlando
This three-bedroom, one-bathroom flat is located on a quiet cobblestone street in Orlando's College Park neighbourhood, 3.2 kilometres from the Kia Centre and within 32 kilometres of Walt Disney World Resort, Universal Orlando Resort, and SeaWorld Orlando.
This 102 square metre apartment accommodates up to five guests and features a private fenced garden with a hot tub, air conditioning, a fully equipped kitchen, and high-speed internet, with free parking for two cars and contactless self-check-in.
349 M² Ferienhaus ∙ 8 Schlafzimmer ∙ 24 Gäste - Winter Park, FL
No reviews

349 M² Ferienhaus ∙ 8 Schlafzimmer ∙ 24 Gäste

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.
2 King En Suite Fenced Yard Pet Friendly - Winter Park, FL
8.0 2 reviews

2 King En Suite Fenced Yard Pet Friendly

house, Orlando
This Orlando holiday home is conveniently located 5km from Church Street Station, offering easy access to the Amway Center (5.3km) and Camping World Stadium (7.7km).
The 123 square metre property boasts two ensuite bedrooms, sleeping up to seven guests, and features a fully equipped kitchen, private parking, a garden with outdoor fireplace and play equipment, plus free Wi-Fi.

Best pet friendly Winter Park, FL vacation rentals

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

Mid Century Modern 3-bedroom House Close To Everything In Orlando Up To 7 Guests - Winter Park, FL
No reviews

Mid Century Modern 3-bedroom House Close To Everything In Orlando Up To 7 Guests

apartment, Altamonte Springs
This Altamonte Springs residence offers a prime location, approximately 12 kilometres from Tinker Field and 16 kilometres from Wekiwa Springs State Park, with the Enzian Theater and Casa Feliz Historic Home Museum nearby for cultural exploration.
This spacious 217 square metre flat accommodates up to seven guests across three bedrooms and two bathrooms, boasting a gourmet kitchen with a waterfall island, a garden, a fireplace, ample parking, and proximity to outdoor activities such as kayaking and fishing.
Upscale 1br Apartment Home - Winter Park, FL
No reviews

Upscale 1br Apartment Home

apartment, Winter Springs
This one-bedroom flat is situated in Winter Springs, a tranquil community located northeast of Orlando, providing straightforward access to shopping, dining, parks, and major roads, with Lake Jesup and Trotwood Park in close proximity.
This 764 square meter apartment, ideal for two guests, features a fully equipped kitchen, open-plan living and dining areas, and access to community amenities including a swimming pool, fitness centre, and tennis court, with nearby outdoor recreation at Lake Jesup and Trotwood Park.
* Beautiful Lakehouse With Pool And Movie Theater* - Winter Park, FL
9.8 35 reviews

* Beautiful Lakehouse With Pool And Movie Theater*

apartment, Casselberry
This Casselberry holiday home is located just 4.7 kilometres from Red Bug Lake Park and within 10 kilometres of Cranes Roost Park and Boombah-Soldiers Creek Park, offering easy access to local attractions. The property has received excellent guest ratings, indicating a high standard of comfort and service.
The house has five bedrooms and two bathrooms, comfortably accommodating up to 16 guests. Enjoy a range of amenities including a private pool, a garden, a terrace, and a fully equipped kitchen, perfect for relaxing and enjoying your stay.
Premium King Suite With Den In Central Orlando | P - Winter Park, FL
9.9 29 reviews

Premium King Suite With Den In Central Orlando | P

apartment, Orlando
This 1-bedroom plus den flat is located in Downtown Orlando, 5 minutes from Lake Eola, the Dr. Phillips Centre for the Performing Arts, and the Kia Centre, with Universal Studios 24 kilometres away and Walt Disney World Resort 43 kilometres away.
This pet-friendly apartment offers resort-style amenities including a swimming pool and fitness centre, a fully-equipped kitchen with stainless steel appliances, and accommodates up to four guests with a king-size bed in the master bedroom and a queen-size bed in the den.
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