Vacation Rentals in Winter Park, FL

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Winter Park, FL vacation rentals
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405 Vacation 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

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.
Stylish Boutique Guest House In Winter Park - Winter Park, FL
10 109 reviews

Stylish Boutique Guest House In Winter Park

apartment, Winter Park
This two-bedroom flat is ideally located in Winter Park, just a short distance from attractions like the Casa Feliz Historic Home Museum and the Morse Museum of American Art. It has received excellent reviews from previous guests.
The apartment comfortably sleeps four guests and features a fully equipped kitchen, a fireplace, and a balcony. Guests can enjoy the on-site fitness centre, swimming pool, and garden, as well as free Wi-Fi and parking.
Stylish & Cozy King Bed Retreat @ Baldwin Park - Winter Park, FL
10 63 reviews

Stylish & Cozy King Bed Retreat @ Baldwin Park

apartment, Orlando
This fully furnished two-bedroom house is situated near Baldwin Park, a short drive (minutes) from Downtown Orlando, Orlando International Airport (MCO), and several theme parks.
The 2-bathroom property, sleeping up to 5 guests, boasts a private backyard with a fire pit, high-speed internet, a fully equipped kitchen including a dishwasher, and keyless entry; peaceful walking trails are also nearby, with Downtown Disney easily accessible.
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.

Best Winter Park, FL holiday rentals with parking

The Louie - Luxe 1br Condo Dt W/ Rooftop Pool, Gym - Winter Park, FL
9.8 11 reviews

The Louie - Luxe 1br Condo Dt W/ Rooftop Pool, Gym

apartment, Orlando
This Orlando apartment, ideally situated in a central location, offers easy access to Downtown Orlando, the Amway Center, and major theme parks such as Disney World and Universal Studios, all within a 8-24 km radius.
The one-bedroom, one-bathroom flat sleeps three guests and boasts a luxe industrial loft design, including a fully equipped kitchen, two 55" TVs, high-speed Wi-Fi, in-unit laundry, private parking, and access to a rooftop lounge, heated pool, and fitness centre.
The Princeton- College Parks Best Kept Secret! - Winter Park, FL
10 92 reviews

The Princeton- College Parks Best Kept Secret!

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.
Suites By The Wellborn - Winter Park, FL
8.8 74 reviews

Suites By The Wellborn

apartment, Orlando
Apartment rental listing with an excellent rating of 88% based on 74 reviews. Your accommodation will be located in Orlando.
Facilities and services: a room service, free parking and a wheelchair friendly access. This apartment in Orlando also has air conditioning!
Comfy Tiny Home @Wp. Large Private Deck+queen Bed - Winter Park, FL
9.6 145 reviews

Comfy Tiny Home @Wp. Large Private Deck+queen Bed

cabin, Winter Park
This Winter Park cottage boasts a unique split-building design, situated in a quiet Orlando neighbourhood approximately 16-24 km from Universal Studios and 32-35 km from Orlando International Airport.
The self-contained unit sleeps three, featuring a queen bed, full kitchen with dishwasher, private patio and deck, a full-size washer/dryer, and dedicated parking for two cars, plus access to a communal BBQ area.

Frequently asked questions about holiday rentals in Winter Park, FL

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Best Winter Park, FL holiday rentals with a balcony

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.
Lake House - Winter Park, FL
9.8 209 reviews

Lake House

apartment, Orlando
This family-friendly house is located near Lake Eola in Orlando, within 1.6 kilometres of Orlando Regional Medical Center and Lake Eola Park, offering easy access to various attractions. The property has consistently received excellent ratings for user experience, location, and cleanliness.
The house has two bedrooms, accommodating up to four guests, and provides a range of amenities for a comfortable stay. Guests can enjoy the swimming pool, jacuzzi, sauna, spa, fitness centre, tennis court, and garden, as well as a fully equipped kitchen and free Wi-Fi.
Charming Home @Wp. Patio +Gazebo. Close To Highwys - Winter Park, FL
No reviews

Charming Home @Wp. Patio +Gazebo. Close To Highwys

house, Winter Park
This 79 square meter residence is situated in the Mills50 district, offering a 2-minute drive to Winter Park and a 7-minute drive to downtown Orlando, with convenient access to major routes for attractions such as Universal Studios (24-32 kilometers) and Walt Disney World (48-56 kilometers).
This family-friendly abode accommodates up to seven guests across two bedrooms, featuring a fully equipped kitchen with an ice maker, air conditioning, a private fenced garden with a gazebo, and parking for two vehicles.
Universal Lakehouse Free Kayaks - Winter Park, FL
10 1 review

Universal Lakehouse Free Kayaks

house, Orlando
This five-bedroom holiday home is located in Orlando, 3.5 kilometres from the Holy Land Experience and 16 kilometres from Orlando International Airport, offering convenient access to Universal Studios Florida and The Wizarding World of Harry Potter.
This spacious residence spans 177 square metres and accommodates up to 18 guests, featuring a fully equipped kitchen, air conditioning, a terrace, private parking, and complimentary kayaks for direct access to outdoor lake activities.

Best pet friendly Winter Park, FL vacation rentals

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

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.
Relaxing Lake House With Ac In Quiet Casselberry - Winter Park, FL
No reviews

Relaxing Lake House With Ac In Quiet Casselberry

apartment, Casselberry
This Casselberry flat, a nature retreat, is located approximately 32 kilometres from downtown Orlando's attractions and about 72 kilometres from Disney.
This two-bedroom, one-bathroom residence accommodates four guests and features a large garden overlooking a lake, a screened porch, and is conveniently situated near the Central Florida Fairgrounds and Wekiwa Springs State Park.
Studio| Wi-fi + Kitchen - Winter Park, FL
8.2 12 reviews

Studio| Wi-fi + Kitchen

house, Orlando
This Orlando duplex, situated in a residential area approximately 16-24 km from Downtown Orlando, the Orlando Science Center, and Thornton Park's shops and restaurants, offers a private unit with its own entrance.
The self-catering property sleeps four, features a fully equipped kitchen, dedicated workspace, and shared patio; two compact cars can park on-site, and pets are welcome (small surcharge applies).
Gem. Downtown Winter Park, Walk To Park Av/rollins - Winter Park, FL
9.8 143 reviews

Gem. Downtown Winter Park, Walk To Park Av/rollins

apartment, Winter Park
This three-bedroom apartment is located on Park Avenue in Winter Park, just a short walk from restaurants, shops, art galleries, the Museum, Park, Rollins College, and the Winter Park Community Center. The apartment is highly rated for its location, cleanliness and overall experience.
The apartment is ideal for families or groups of friends, providing comfortable accommodation for up to six guests. It offers a fully equipped kitchen, a garden, parking, and air conditioning, as well as access to the internet.
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