Holiday Rentals in Winter Park, FL

405 available vacation rental offers

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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

Walk Into Tropical Paradise - Pool - Gym - Hot Tub - Winter Park, FL
9.4 27 reviews

Walk Into Tropical Paradise - Pool - Gym - Hot Tub

apartment, Altamonte Springs
This Altamonte Springs holiday home, conveniently located near Interstate 4, offers easy access to Orlando's theme parks and is within a short distance of Altamonte Springs' shopping and dining areas.
Sleeping up to nine guests, this four-bedroom, two-bathroom property boasts a private backyard with a pool, hot tub, mini-golf, and yard games, plus a fully equipped kitchen, home gym, and multiple large-screen TVs.
City And Stadium Sanctuary Vibes - Winter Park, FL
10 1 review

City And Stadium Sanctuary Vibes

house, Orlando
This Orlando holiday home is conveniently located near Camping World Stadium, approximately 2.3km from Church Street Station and within a 12km radius of Universal Studios and Islands of Adventure.
The 116 square metre property features one bedroom, one bathroom, and sleeps up to 15 guests, boasting a fully equipped kitchen, private parking, and complimentary Wi-Fi.
Cozy Home In Dwtn + 6 Guests! - Winter Park, FL
No reviews

Cozy Home In Dwtn + 6 Guests!

apartment, Orlando
This two-bedroom flat is situated in Orlando's Lawsona - Fern Creek district, offering proximity to Lake Eola Park (1 km walk) and the Kia Center (3-minute drive).
This family-friendly apartment accommodates six guests and includes a kitchen with a fridge, microwave, and dishwasher, plus air conditioning, Wi-Fi, and on-site parking, with nearby activities like bird watching and amusement parks.
Peaceful Private Gated Patio Walk To Mall Publix - Winter Park, FL
9.8 47 reviews

Peaceful Private Gated Patio Walk To Mall Publix

apartment, Altamonte Springs
This studio apartment is located in a peaceful, secluded area of Altamonte Springs, just a short walk from a shopping mall, a park, and a Publix grocery store. The apartment has received excellent ratings for its location, cleanliness, and overall experience.
The compact studio is perfect for solo travellers or couples, and can comfortably accommodate up to four guests. The apartment offers a range of amenities, including a fully equipped kitchen, air conditioning, a private patio, access to a fitness centre, and ample parking.

Best Winter Park, FL holiday rentals with parking

B&d Peacock - Winter Park, FL
10 3 reviews

B&d Peacock

apartment, Winter Park
This family-friendly flat in Winter Park offers excellent access to downtown Orlando, located just a short drive away, and places you within walking distance of numerous restaurants, shops, and entertainment venues.
This comfortable three-bedroom, two-bathroom residence accommodates up to seven guests and features essential amenities including air conditioning, a fully equipped kitchen with a fridge, microwave, and dishwasher, and off-street parking, with a garden also available for use.
Hogar Sobre Ruedas - Winter Park, FL
10 2 reviews

Hogar Sobre Ruedas

apartment, Rio Pinar
This self-catering apartment in Orlando's Rio Pinar neighbourhood is conveniently located approximately 15-21 kilometres from attractions such as Church Street Station, the Kia Center, Camping World Stadium, and the Holy Land Experience.
The one-bedroom, one-bathroom flat sleeps three guests and features a private terrace with garden views, free Wi-Fi, private parking, air conditioning, and a fully equipped kitchen.
Cozy 2/2 Home - Downtown Winterpark/orlando - Winter Park, FL
9.9 352 reviews

Cozy 2/2 Home - Downtown Winterpark/orlando

bungalow, Fairview Shores
This charming bungalow in College Park is ideally situated for exploring Fairview Shores, with easy access to Downtown Orlando, Downtown Edgewater, Downtown Winter Park, Universal Studios, and Disney. The property has consistently received excellent reviews for its location, cleanliness, and overall experience.
The two-bedroom, two-bathroom property can comfortably accommodate up to five guests. You'll enjoy modern amenities, a spacious entertainment area with a large TV, comfortable bedrooms, and Bluetooth music in both bathrooms.
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 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

Corner 1bedroom Unit Near Downtown - Winter Park, FL
8.0 5 reviews

Corner 1bedroom Unit Near Downtown

apartment, Orlando
This one-bedroom flat is located in the historic Lake Cherokee neighbourhood of Orlando, offering private access to downtown and situated approximately 8 kilometres from Universal Orlando Resort and Universal Studios Florida.
This family-friendly apartment accommodates up to four guests and features a modern kitchen, air conditioning, a private porch, and two smart TVs with streaming services, with assigned parking available.
*Travel Themed Property With Backyard Oasis* - Winter Park, FL
9.8 40 reviews

*Travel Themed Property With Backyard Oasis*

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.
Cozy Home 5min To Park Ave And Downtown Orlando - Winter Park, FL
No reviews

Cozy Home 5min To Park Ave And Downtown Orlando

apartment, Fairview Shores
This two-bedroom flat in Fairview Shores, Winter Park, is situated within easy reach of leisure parks and offers convenient access to retail at Lee Road Shopping Centre, just an 11-minute walk away, and educational excursions to the Orlando Science Centre, a 4-minute drive.
This well-appointed apartment sleeps six guests and features a full kitchen, air conditioning, complimentary Wi-Fi, and a garden, with on-site parking provided for your convenience.
Luxury House - Sleeps 8, Golf, Disney, Family Fun! - Winter Park, FL
10 4 reviews

Luxury House - Sleeps 8, Golf, Disney, Family Fun!

apartment, Orlando
This Orlando property, a luxurious two-bedroom house in the Ventura neighbourhood, is conveniently located near Universal Orlando Resort and Walt Disney World Resort, approximately a short drive from both.
The 189-square-metre home sleeps six, features two bathrooms, a fully equipped kitchen including a dishwasher, and offers a garden, terrace, and parking; guests can also enjoy cycling in the local area.

Best pet friendly Winter Park, FL holiday rentals

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

Home Away From Home In Orlando! - Winter Park, FL
9.4 34 reviews

Home Away From Home In Orlando!

house, Casselberry
This Casselberry holiday home is situated approximately 16 kilometres from both the Addition Financial Arena and Spectrum Stadium, offering easy access to Orlando's attractions.
This recently renovated four-bedroom property boasts 186 square metres of space, sleeping up to 23 guests and featuring a fully equipped kitchen, private garden, terrace, and free Wi-Fi.
Tranquil Hideaway: 2-bedroom Retreat Near Mills/50 - Winter Park, FL
8.8 5 reviews

Tranquil Hideaway: 2-bedroom Retreat Near Mills/50

apartment, Orlando
This three-bedroom Colonialtown North apartment in Orlando, Florida, is situated 1.1 kilometres from Harry P. Leu Gardens and within a 3-5 kilometre radius of the Plaza Theatre and Orlando Museum of Art.
The 3-bedroom property sleeps five guests and features a fully equipped kitchen, free Wi-Fi, a garden, and parking; nearby attractions include the Kia Centre and on-site barbecue facilities.
Renovated Peaceful Luxury Walk To Mall Park Publix - Winter Park, FL
9.0 22 reviews

Renovated Peaceful Luxury Walk To Mall Park Publix

apartment, Altamonte Springs
This Altamonte Springs holiday home is conveniently located less than 1.6km from Altamonte Mall and Cranes Roost Park, and around 3.2km from Sanlando Park.
The one-bedroom, one-bathroom property sleeps four guests and offers a fully equipped kitchen, in-unit laundry, free Wi-Fi, a smart TV, and access to an on-site fitness centre.
10 Minutes To Downtown With Jacuzzi, Pool Table, Ping Pong, And Bbq - Winter Park, FL
9.7 3 reviews

10 Minutes To Downtown With Jacuzzi, Pool Table, Ping Pong, And Bbq

house, Orlando
This Orlando dwelling is situated approximately 7.6 kilometres from downtown attractions such as the Kia Centre and Church Street Station.
This property offers 157 square metres of living space, accommodating up to 19 guests with a fully equipped kitchen, a pool table, ping pong, a private hot tub, and complimentary WiFi.