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Winter Park, FL apartments
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321 Apartments or condos in Winter Park, FL

Find Apartments in Downtown of Winter Park, FL

Live like a local by choosing downtown apartments in Winter Park, FL, offering seamless walking access to top restaurants and shopping districts.

Barbour House 530 - Winter Park, FL
10 7 reviews

Barbour House 530

apartment, Winter Park
This Winter Park apartment rental is located one block from Park Avenue, offering easy access to restaurants, shops, and the city's parks.
The two-bedroom, two-bathroom unit features a private garden accessible via French doors from the living room and master bedroom, sleeps four guests, and includes a fully equipped kitchen with a refrigerator, microwave, and dishwasher.
Barbour House 200 With King Size Bed - Winter Park, FL
10 4 reviews

Barbour House 200 With King Size Bed

apartment, Winter Park
This two-bedroom, two-bathroom apartment in Winter Park's historic Barbour House is located one block from Park Avenue, offering easy access to upscale shopping and dining.
The 4-guest unit features a fully equipped kitchen, private balcony, and superior bedding in the master suite, all within a short drive of Walt Disney World and Florida's beaches.
Winter Park Oasis - Winter Park, FL
9.6 27 reviews

Winter Park Oasis

apartment, Winter Park
This charming vacation home is conveniently located in Winter Park, just a short distance from Kraft Azalea Gardens and Winter Park Village, offering easy access to local attractions and shopping. Guests have consistently rated this property as excellent, highlighting its comfortable accommodations and convenient location.
This two-bedroom home comfortably accommodates up to four guests, providing ample space for families or groups of friends. Enjoy the Florida weather on the patio or relax in the garden, while the fully equipped kitchen allows you to prepare meals at your leisure.
Barbour House 300 With King Size Bed - Winter Park, FL
10 18 reviews

Barbour House 300 With King Size Bed

apartment, Winter Park
This one-bedroom Winter Park apartment, located in the historic Barbour House, is one block from Park Avenue's upscale shopping and dining.
The unit features a fully equipped kitchen, a private balcony, and accommodates two guests in a professionally decorated space offering a superior bed and fine linens.

Best Winter Park, FL apartment rentals with air conditioning

Downtown Orlando-harwood House-lake Eola-historic - Winter Park, FL
9.8 279 reviews

Downtown Orlando-harwood House-lake Eola-historic

apartment, Orlando
This completely renovated guesthouse is located in the Eola Heights Historic District, just three blocks from Lake Eola and within walking distance of downtown Orlando's dining, shopping, and entertainment options. The apartment has earned excellent ratings for cleanliness, location, and user experience.
The 424 square-foot guesthouse offers a comfortable living space with a separate pull-out sofa, accommodating up to 4 guests. The unit features a fully equipped kitchen with modern appliances, a washer and dryer, two flat-screen TVs, and comfortable queen-sized beds.
1br 1ba In Historic Park Ave Home - Winter Park, FL
10 6 reviews

1br 1ba In Historic Park Ave Home

apartment, Winter Park
This 1-bedroom condo is located in Orlando's historic Park Avenue district, a 15-minute walk from the Enzian Theater and within 1 mile of the Winter Park Municipal Golf Club and the Charles Hosmer Morse Museum of American Art.
This 400 sq ft unit accommodates up to 2 guests and features a private swimming pool, kitchenette with a microwave and fridge, air conditioning, and garden views.
7.3miles To Airport + 20miles To Disney + 8.2miles To Dt! - Winter Park, FL
8.6 11 reviews

7.3miles To Airport + 20miles To Disney + 8.2miles To Dt!

apartment, Orlando
This Orlando vacation home is located near Ventura Country Club, just a short distance from shopping centers and Lake Conway. Guests rave about the excellent user ratings, highlighting the home's comfort and convenience. This 3-bedroom house comfortably sleeps 10 guests, making it perfect for families or groups of friends. Enjoy a fully equipped kitchen, a relaxing patio, and easy access to outdoor activities like fishing and boating.
1 Full Bed  Ada/tub/micfridge - Winter Park, FL
No reviews

1 Full Bed Ada/tub/micfridge

apartment, Fairview Shores
This apartment is located in Orlando, approximately 5.6 miles from the Kia Center and Church Street Station, and 13.7 miles from Universal Studios' Islands of Adventure.
This 200 sq ft, pet-friendly studio offers air-conditioned accommodation for up to 2 guests, featuring a private bathroom, TV, free WiFi, refrigerator, microwave, and access to an outdoor swimming pool and on-site parking.

Frequently Asked Questions about apartment rentals in Winter Park, FL

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Check Out Apartments with Balconies in Winter Park, FL

Step onto your own terrace and take in the skyline; every vacation apartment of Winter Park, FL on this list includes private outdoor space.

Landing Stunning 1bd Rooftop Lounge Gym - Winter Park, FL
No reviews

Landing Stunning 1bd Rooftop Lounge Gym

apartment, Orlando
Accommodation. Your accommodation will be based in Orlando.
Services and facilities: a terrace, an iron and a washing machine.
The Pied-à-terre In Downtown - Winter Park, FL
10 2 reviews

The Pied-à-terre In Downtown

apartment, Orlando
This Orlando bungalow, located in the Lake Eola Heights Historic District, is within walking distance of Downtown Orlando and Lake Eola Park, and a short drive (20-30 minutes) from Universal Studios, SeaWorld, and Disney Parks.
This 2-bedroom, 2-bathroom house features original 400-year-old Long Leaf Pine floors, a lush garden, and accommodates up to 5 guests, offering a blend of historic charm and modern amenities.
Dt505 - 1br Downtown Bungalow In Orlando - Winter Park, FL
8.0 1 review

Dt505 - 1br Downtown Bungalow In Orlando

apartment, Orlando
This pet-friendly bungalow, located in Orlando's Lake Davis-Greenwood neighborhood, is steps from Lake Eola Park and near Universal Orlando Resort, Florida Mall, and Orlando International Premium Outlets.
The one-bedroom, one-bathroom cottage offers guests a fully equipped kitchen with a fridge, microwave, and dishwasher, a private backyard, parking for two cars, and accommodates up to two people.
Landing | Chic 2bd, Rooftop Lounge, Courtyard - Winter Park, FL
No reviews

Landing | Chic 2bd, Rooftop Lounge, Courtyard

apartment, Orlando
This furnished 2-bedroom, 2-bathroom condo in Downtown Orlando offers 840 square feet of living space for up to 4 guests, featuring a fully equipped kitchen and in-unit laundry, ideal for extended stays.
Enjoy convenient access to Florida Mall, Orlando International Premium Outlets, Universal Orlando Resort, and the Kia Center, with on-site amenities including a pool, hot tub, yoga studio, and fitness center with city views.

Neighborhoods and points of interest in Winter Park, FL

Best Family Apartments in Winter Park, FL

These family-friendly vacation apartments in Winter Park, FL offer plenty of space with city attractions within easy reach.

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 Orlando vacation home is near Ivanhoe Village and Mills districts, minutes from I-4, Dubsdread Golf Course, AdventHealth, and downtown Orlando.
The three-bedroom, two-bathroom house sleeps eight, features a private backyard with a fire pit and gazebo, a "cowboy pool," and offers keyless entry, high-speed Wi-Fi, and streaming services.
*Travel Themed Property With Backyard Oasis* - Winter Park, FL
9.8 40 reviews

*Travel Themed Property With Backyard Oasis*

apartment, Casselberry
Centrally located in Maitland, within walking distance of Walmart Supercenter and various restaurants, "The Terminal" is a highly-rated 6-bedroom apartment that offers a unique travel-themed experience.
With a floor area of 2500 square feet, it can accommodate up to 14 guests and features a private screened-in pool, an outdoor kitchen, a fire pit, a game room with an 85" TV, air hockey table, and Atari arcade console, as well as nine HD TVs throughout the apartment.
Downtown Gem W/ Jacuzzi + Basketball + Games! - Winter Park, FL
No reviews

Downtown Gem W/ Jacuzzi + Basketball + Games!

apartment, Orlando
This three-bedroom, two-bathroom vacation rental in Orlando's Lake Eola Heights neighborhood is conveniently located 0.6 miles from Lake Eola, 1.5 miles from the Amway Center, and within easy driving distance of Universal Studios (11 miles) and Walt Disney World (21 miles).
The 3-bedroom home features a spacious tropical backyard with a jacuzzi, accommodates up to 9 guests (with an option for 11 for an extra fee), and includes a fully equipped kitchen, smart TVs, free Wi-Fi, a washer/dryer, and various coffee makers (Keurig, Nespresso, drip).
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 Colonialtown North rental is conveniently located 0.7 miles from Harry P. Leu Gardens and within 2 miles of the Plaza Theatre and Orlando Museum of Art.
This three-bedroom, one-bathroom apartment sleeps five, features a fully equipped kitchen with appliances including a microwave and refrigerator, free WiFi, and a garden, plus offers parking and is pet-friendly.

Our Favorite Apartments with Parking in Winter Park, FL

Driving to Winter Park, FL? Each of these apartments include parking, making city center access simple from the moment you arrive.

Lake Eola View 1 Bedroom Thornton Park - Winter Park, FL
10 15 reviews

Lake Eola View 1 Bedroom Thornton Park

apartment, Orlando
Downtown (Ivanhoe Village) Loft Apartment - Winter Park, FL
9.8 1358 reviews

Downtown (Ivanhoe Village) Loft Apartment

apartment, Orlando
Funky Remodeled Otown Bungalow Sleeps 8 - Winter Park, FL
9.7 160 reviews

Funky Remodeled Otown Bungalow Sleeps 8

apartment, Winter Park
Thornton Park Paradise 1 Bedroom Lake Eola - Winter Park, FL
10 4 reviews

Thornton Park Paradise 1 Bedroom Lake Eola

apartment, Orlando

Top-Rated Luxury Apartments in Winter Park, FL

A city-center luxury vacation apartment in Winter Park, FL sets a wonderful tone for your visit, offering 5-star comfort throughout.

Cozy Private Apartment In Casselberry - Winter Park, FL
10 6 reviews

Cozy Private Apartment In Casselberry

apartment, Casselberry

Explore Pet-Friendly Apartments in Winter Park, FL

A quality pet-friendly vacation apartment in Winter Park, FL means nearby dog parks and city walks are just steps away from your front door.

Private Luxury Pool / Swim Up Bar / Smart-home - Winter Park, FL
9.7 334 reviews

Private Luxury Pool / Swim Up Bar / Smart-home

apartment, Orlando
Chic 2br Condo In The Heart Of Orlando Downtown - Winter Park, FL
10 1 review

Chic 2br Condo In The Heart Of Orlando Downtown

apartment, Orlando
Modern Comfort: Mills/50 Hideaway - Winter Park, FL
8.4 5 reviews

Modern Comfort: Mills/50 Hideaway

apartment, Orlando
Home Away From Home In The Heart Of Charming Winter Park! - Winter Park, FL
10 5 reviews

Home Away From Home In The Heart Of Charming Winter Park!

apartment, Winter Park

Compare Apartments with a Pool in Winter Park, FL

Choosing a vacation apartment in Winter Park, FL with a pool ensures a proper swim in the heart of the city is always an option.

Spacious 5-bedroom House In Charming Orlando With Ac - Winter Park, FL
10 6 reviews

Spacious 5-bedroom House In Charming Orlando With Ac

apartment, Fairview Shores
Long Stays Welcome! - Winter Park, FL
No reviews

Long Stays Welcome!

apartment, Winter Park
Light, Bright And Full Of Delight! 2 Blocks To Park Ave - Winter Park, FL
10 1 review

Light, Bright And Full Of Delight! 2 Blocks To Park Ave

apartment, Winter Park
Winter Park Citrus Escape; Sleeps 8, Relaxing Pool, Family & Pet Friendly - Winter Park, FL
9.0 33 reviews

Winter Park Citrus Escape; Sleeps 8, Relaxing Pool, Family & Pet Friendly

apartment, Goldenrod

Search Apartments with a Hot Tub in Winter Park, FL

A vacation apartment with a hot tub in Winter Park, FL is perfectly designed for a private soak at the end of a long day.

Wana Chill Spot    *Pool *Spa *Bar *Ping Pong *Bbq - Winter Park, FL
10 50 reviews

Wana Chill Spot *Pool *Spa *Bar *Ping Pong *Bbq

apartment, Casselberry
Lakefront House With Private Pool. Lake Sunsets - Winter Park, FL
9.8 84 reviews

Lakefront House With Private Pool. Lake Sunsets

apartment, Orlando
Tropical Pool & Spa Home, 3/2, Near Disney, Universal, Sea World, Beaches - Winter Park, FL
10 12 reviews

Tropical Pool & Spa Home, 3/2, Near Disney, Universal, Sea World, Beaches

apartment, Altamonte Springs
Private Outdoor Oasis W/ Pool: Home In Longwood! - Winter Park, FL
9.6 11 reviews

Private Outdoor Oasis W/ Pool: Home In Longwood!

apartment, Longwood
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