Best Apartments in Winter Park

Top Apartment Rentals in Winter Park

Find your ideal city escape with our handpicked apartment selections in Winter Park, designed for those seeking both comfort and style during their stay.

Apartments in Winter Park
1BR 1BA in Historic Park Ave Home
Apartment
1645 North Park Avenue, Orlando, FL, FL 32789, USA

1BR 1BA in Historic Park Ave Home is a recently renovated apartment in Orlando where guests can make the most of the seasonal outdoor swimming pool and garden. The air-conditioned accommodation is 5.7 miles from Kia Center. There's a sun terrace and guests can use free Wifi and free private parking. Featuring a patio with pool views, this apartment also comes with a flat-screen TV, a well-equipped kitchenette with a microwave, a fridge, and kitchenware, as well as 1 bathroom with a walk-in shower and a hair dryer. For added privacy, the accommodation has a private entrance and is protected by full-day security. The apartment also features outdoor fireplace and a picnic area for a day outdoors. Church Street Station is 5.7 miles from the apartment, while Camping World Stadium is 6.9 miles from the property. Orlando International Airport is 13 miles away.

Amenities:

Security/Safety • Oceanfront • Fireplace/Heating • Balcony/Terrace • Sports/Activities • Internet • Air Conditioner • Laundry • View • Ocean View • Other • Pool

Apartments in Winter Park
College quater charming Winter Park Historic Dist Rollins College quarters
Apartment
Winter Park, Florida, USA

The College Quarters in Winter Park is located in the charming city of Winter Park Historic District. Located within blocks. of SunRail stations, shopping, movie theatres, grocery, gas stations, banks, and golf courses, and Rollins College founded in1885 along the shores of Lake Virginia

Guest Reviews:

- "Amazing location and greatly enjoyed the short walk to park ave!!!" - "Property could use updating and kitchen is minimal at best but location is amazing for park ave food and shopping and Rollins college"

Apartments in Winter Park
Quiet Location Duplex House - Minutes Away from Everything - Winter Park, Florida
Apartment
5030 Oak Hill Drive, Orlando, FL, FL 32792

Quiet Location Duplex House - Minutes Away from Everything - Winter Park, Florida offers accommodations in Orlando, 6.7 miles from Addition Financial Arena and 7.1 miles from Spectrum Stadium. Both free Wifi and parking on-site are accessible at the apartment free of charge. Camping World Stadium is 11 miles away, and Holy Land Experience is 16 miles from the apartment. All of the air-conditioned units feature a private bathroom, flat-screen TV, and fully equipped kitchen. Kia Center is 9.3 miles from Quiet Location Duplex House - Minutes Away from Everything - Winter Park, Florida, while Church Street Station is 10 miles from the property.

Amenities:

Guest Services • Security/Safety • Pet Friendly • Fireplace/Heating • Child Friendly • Air Conditioner • Parking • Other • Internet

Apartments in Winter Park
Charming 2-bedroom apartment with AC and WiFi in enchanting Winter Park
Apartment
Winter Park, Florida, USA

Located in Winter Park, this apartment is a dream. With 2 nice bedrooms, AC, WiFi, a hair dryer, an iron, and a washing machine, guests will find everything they need for a comfortable stay. The bathroom is marvelous, adding a touch of luxury to the space. We hope you enjoy what our place and Winter Park has to offer.

Amenities:

Fireplace/Heating • Smoking • Laundry • Pet Friendly • Internet • Air Conditioner • Wellness Facilities • Bedding/Linens

Apartments in Winter Park
Charming CozyLux 2-bedroom apartment
Apartment
Winter Park, Florida, USA

Escape to this enchanting apartment in picturesque Winter Park. This cozy retreat features 2 bedrooms with a king bed, queen bed, and futon, along with 2 bathrooms equipped with all the essentials. With amenities like AC, a washing machine, and WiFi, guests will feel right at home. You're sure to make fantastic memories with a stay at our place.

Amenities:

Security/Safety • Other • Bedding/Linens • Air Conditioner • Laundry • Fireplace/Heating • Child Friendly • Internet • Wellness Facilities

Apartments in Winter Park
Mid Century Luxury, 1 block from Park Ave (#3)
Apartment
Winter Park, Florida, USA

This 2nd floor apartment is nestled under oaks on a quiet cobblestone street in downtown Winter Park. There are only 3 units on the property, which helps to evoke a quiet, serene atmosphere. When you are ready to explore, Park Ave is only a block away and literally visible from your front door. Shops, bars and restaurants are within a 3 minute stroll. The famous Saturday morning Farmers Market , Rollins College and the Scenic Boat Tour are all within a fifteen minute walk. The Beaches and Theme Parks are easily accessed via the interstates.

Guest Reviews:

- "I just want everyone to be properly prepared for the rental. The location is excellent you walk one block to park ave where all the shopping and restaurants are located First of all when you arrive university beautiful area but the property itself is a much older 1960s building there is some issues with parking, very very tight space and limited to one spot. there is some safety issues with a retaining wall at the front of the property that's collapsing so if you have children be careful. THE NEIGHBORHOOD: excellent THE PROPERTY: very old complex dates with some safety issue at front of the property will a collapsing wall. THE UNIT: on the second floor, overall small two bedroom furnished with very outdated 1970 furniture and green color. BEDROOM:Bedding is excellent with one master with a queen bed and one d Bedroom with two single beds for kids. KITCHEN:: updated and modern with EVERY AMENITY AND COOKING UTENSILS REQUIRED😊. Well stocked!! BATHROOM: updated small well stocked with excellent hair products shampoo conditioner hairdryer and curling iron😊 LINEN AND TOWELS: well stocked. Overall I enjoyed my stay I did not use the kitchen please be aware the door on the refrigerator is very flimsy and doesn't close properly so please be cognizant of this the owner furnishes and supplies you with excellent products I was pleasantly surprised. Overall as I stated an excellent stay but very disappointed in the quality of the furniture and the appearance of the complex"

Apartments in Winter Park
Modern apartment with enclosed yard, central AC, & kitchenette - dog-friendly
Apartment
Winter Park, Florida, USA

Hop Top Rental

Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired dates and click 'Book Now!'

The gateway to your dream Florida vacation, this charming studio stay is nestled a quick drive away from Walt Disney World, the airport, and downtown historic Winter Park. When you want to play in the sand and the surf, you can easily take a day trip to the beach, about 45 minutes away.

When you're ready to relax, unwind, and recuperate; lounge on the plush sofas while tuning into a movie on the large TV. The kitchenette comes well-equipped with a small fridge/freezer, a coffee maker, a microwave, a hot plate, and a toaster.

Additionally inside you will find a phone-controlled mirror, central air-conditioning, and free WiFi. Outside, the small fenced-in yard provides the perfect space for the furry members of your family to stretch their legs.

Sleep will come easy tucked under the soft bedding on the bed and on the two pull-out sofas.

Things to Know
Check-in time: 4:00 PM
Check-out time: 10:00 AM
All guests shall abide by Vacasa's good neighbor policy and shall not engage in illegal activity. Quiet hours are from 10:00 PM to 8:00 AM
No smoking is permitted anywhere on the premises.
This property is not equipped with a washer and dryer.
A single cot with a mattress is available upon request.

This Vacasa Guestworks vacation rental is operated and managed locally by an independent host.
Prior to your arrival, you will receive local host contact information, who will manage your guest reservation. Your local host will provide in-stay support, secure entry, and arrange pre- and post-stay housekeeping services.
If you need anything during your stay, the home’s independent local host is ready to help 24/7! Guestworks is a service offering of Vacasa that allows homeowners to smoothly and efficiently manage their own properties.

If you are bringing a dog on your trip, the pet fee is already included in your quote when selecting ‘Yes’ to pets. If you would like to add more dogs, please contact us.

Parking notes: There is free parking available for 2 vehicles.

Security camera details: This property is equipped with 2 cameras: (1) at the entry gate, (1) on the garage facing the driveway.

Damage waiver: The total cost of your reservation for this Property includes a nightly damage waiver fee, plus tax if applicable (the “Damage Waiver”). (A discount may be applied for stays of 28 nights or longer, if permitted.) The Damage Waiver covers you for up to $3,000 of accidental damage to the Property or its contents (such as furniture, fixtures, and appliances) as long as you report the incident to the host prior to checking out. The Damage Waiver fee eliminates the need for a traditional security deposit.
More information can be downloaded from the "Rental Agreement" on the checkout page.

Due to local laws or HOA requirements, guests must be at least 21 years of age to book. Guests under 21 must be accompanied by a parent or legal guardian for the duration of the reservation.

Guest Reviews:

- "My husband, fur baby and I stayed for 6 days and it was perfect for us! Studio is spacious and furnishings are plush and comfortable! I personally met Crystal, the hostess and she was very sweet and accommodating! Looking forward to staying here again!" - "Rating Details: The property manager was very helpful. The vacation rental was spotless. I was very happy with the location. I was very satisfied with the condition of the vacation rental. Overall, I recommend this vacation rental. Reviewer Comments: We stayed for 2 weeks and loved it. First class all the way. Beautiful decor and very spacious. Would recommend to anyone!!"

Apartments in Winter Park
Mid Century Luxury, 1 block from Park Ave (#2)
Apartment
Winter Park, Florida, USA

This ground floor apartment is nestled under oaks on a cobblestone street in downtown Winter Park. There are only 3 units on property, which helps encourage a quiet, serene atmosphere. When you are ready to explore, Park Ave is one block away and visible from your front door. Shops, Bars and restaurants are all within a 3 minute stroll. Golf, the Saturday morning Farmers Market, Rollins College and the Scenic Boat tour are all within a fifteen minute walk. The Theme Parks and Beaches are also easily accessible via the interstates.

Guest Reviews:

- "Great property and awesome location!" - "The apartment is well maintained and has a mid century personality. The vintage furnishings are comfortable. The kitchen provides for all cooking needs which we loved. The best for us was the location which allowed for walking around the town. We look forward to returning." - "The best compliment you can give a host and their property is to return. This is at least our third time to stay in this home. Thanks Michael, you have been so kind and gracious to our family and have been so flexible with all our spur of the moment decisions to visit our grandchildren. The location and decor of your home is unmatched in Winter Park, Rick&Barri"

Apartments in Winter Park
Adorable 1 Bedroom in the perfect location!
Apartment
Winter Park, Florida, USA

Our fully renovated, pet-friendly apartments are located in one of the most sought-after neighborhoods in the area, just across from beautiful Lake Baldwin and minutes away from Park Avenue's shops and restaurants. And with all of the incredible features and amenities we offer, you won't find a better deal anywhere else.

Guest Reviews:

- "Place was very clean, nice area, very comfortable bed. Very basic kitchen suppies. A dresser and some end tables would be nice and a bit more communication would have been nice. No hot tub at the complex, no instructions on accessing the pool. Nice neighbors and very dog friendly area. Overall a nice place to stay, a few small improvements would make it even better." - "This apartment is in a nice, quiet area!" - "We came for the AAU Regionals Track & Field Competition. As my baby girl was competing in multiple events I need a place that was very quiet & very close to the event site so we can just crawl in & crash after a long bot day. This place brought it all! Exactly what you see is what you get with some personal touches and a homey feeling. Communication from the host was super fast and easy. Perfect location for everything you need. I will definitely choose this place again. Thank you for having us."

Apartments in Winter Park
Cozy Winter Park 2BR with Garden & Full Kitchen
Apartment
Winter Park, Florida, USA

Summary:
》Tap ‘♡ Save’ to lock in your stay at this peaceful 2-bedroom duplex in Winter Park — where comfort meets convenience.

✦ Cozy 2-bedroom retreat with plush bedding
✦ Fully equipped kitchen for easy home-cooked meals
✦ Relaxing living area with cable TV & fast Wi-Fi
✦ Peaceful patio and garden space
✦ Family- & pet-friendly, with essentials provided

Book your Winter Park escape now—comfort awaits!

The Space:
★ Peaceful & Private Winter Park Getaway ★

》Step into your cozy retreat in the heart of Winter Park — a peaceful, two-bedroom duplex designed for comfort, ease, and relaxation. Whether you're here to explore, work remotely, or simply unwind, every detail has been thoughtfully chosen to make you feel right at home.

★ PRIME LOCATION ★
This home is ideally situated in a lively and charming neighborhood, putting you close to top attractions, trendy restaurants, and local hotspots:
✔ Park Avenue District – A charming street filled with boutique shops, galleries, and delightful cafés
✔ Charles Hosmer Morse Museum – Home to world-famous Tiffany glass and stunning artwork
✔ Winter Park Scenic Boat Tour – Cruise through clear lakes with views of lush gardens and beautiful estates
✔ Mead Botanical Garden – A serene 47-acre nature escape with trails, butterfly gardens, and boardwalks
✔ Kraft Azalea Garden – A quiet lakefront park perfect for peaceful strolls and bird watching
✔ Winter Park Farmers’ Market – A Saturday favorite featuring fresh produce, flowers, and artisan goods
✔ Rollins College – A beautiful historic campus with lake views and walking paths
✔ Albin Polasek Museum & Sculpture Gardens – Explore art and nature side by side
✔ Winter Park Playhouse – Enjoy live musicals and community performances year-round
✔ Central Park – The heart of Winter Park, with shady trees, fountains, and a relaxing open space

★ COMFORTABLE SLEEPING ARRANGEMENTS – 2 BEDROOMS ★
Rest easy in two beautifully appointed bedrooms that welcome you into total comfort:

⓵ King bed
⓶ Queen bed

★ 1 BATHROOM ★
Freshen up in a sparkling clean bathroom equipped with everything you need for your stay:

⓵ Full bathroom with a bathtub

★ LIVING AREA ★
Relax, recharge, or get a little work done in our warm and cozy living room, where comfort meets function:
✔ Cable TV
✔ Fast Wi-Fi
✔ Comfortable sofa with extra pillows and blankets
✔ Dedicated workspace for remote work or travel planning

★ KITCHEN ★
Unleash your inner chef or enjoy a simple snack in our fully stocked kitchen, perfect for whatever you're craving:
✔ Brew up a morning delight with the coffee maker
✔ Stove, microwave, and refrigerator for everyday meals
✔ Cookware, dishes, and silverware for easy dining

★ LAUNDRY ★
Stay fresh with in-unit laundry – ideal for longer stays:
✔ Washer and dryer
✔ Iron and hangers

★ PATIO AND BACKYARD ★
Step outside and enjoy the calm, sunny charm of Florida in your private outdoor space:
✔ Peaceful garden/backyard to relax in fresh air
✔ Cozy patio – perfect for morning coffee or evening wine

★ PET FRIENDLY ★
Bringing your furry friend? We welcome pets!
✔ Small pets allowed — just review our pet policy

★ SAFETY FEATURES ★
Your peace of mind matters:
✔ Smoke detector
✔ Carbon monoxide detector
✔ Fire extinguisher

★ YOUR PERFECT GETAWAY AWAITS ★
Whether you're staying for a weekend escape or an extended break, this duplex is designed with care to make your trip simple, cozy, and memorable.

Guest Access:
★ Book Your Winter Park Getaway Today! ★
This peaceful home is waiting to welcome you — don’t miss your chance to experience the best of Winter Park.

The Neighborhood:
Located in the heart of Winter Park, this neighborhood offers a perfect mix of charm, convenience, and culture. Known for its canopy-lined streets and classic Florida architecture, the area is just minutes from Park Avenue—Winter Park’s signature downtown destination. Guests can stroll through boutique shops, enjoy locally roasted coffee, dine al fresco at gourmet restaurants, or browse fine art galleries, all set against a backdrop of historic buildings and lush greenery.

For those looking to connect with nature, the nearby Winter Park Chain of Lakes provides opportunities for scenic boat tours, paddleboarding, and kayaking. Central Park serves as a welcoming green space for picnics or leisurely walks, while the serene Mead Botanical Garden and Kraft Azalea Garden offer peaceful escapes under grand cypress trees. The area’s natural beauty blends seamlessly with its elegant, laid-back vibe.

Cultural highlights include the Morse Museum, showcasing the world’s most extensive collection of Tiffany glass, and the Cornell Fine Arts Museum at Rollins College. Regular art festivals, outdoor concerts, and a bustling weekly farmers market reflect the community’s vibrant spirit. With easy access to grocery stores, fitness studios, and everyday essentials, guests will enjoy both the charm of a small-town atmosphere and the convenience of city-like amenities.

Getting Around:
Winter Park, Florida, offers a variety of transportation options to help visitors navigate the area with ease. The SunRail commuter train provides a convenient connection between Winter Park and downtown Orlando, with the local station situated near Central Park and Park Avenue. This makes it an excellent choice for travelers looking to explore the broader Orlando region without the need for a car. ​

For local travel, the LYNX bus system operates several routes through Winter Park, including routes 1, 9, and 13, which connect key destinations such as Rollins College, Full Sail University, and Winter Park Village. These buses offer an affordable and reliable way to reach various attractions and neighborhoods within the city.​

Additionally, ride-sharing services like Uber and Lyft are readily available throughout Winter Park, providing flexible transportation options for visitors. For those who prefer a more active mode of travel, the city has installed numerous bike racks and offers bike rental services, allowing guests to enjoy the scenic beauty of Winter Park at their own pace. ​

Other Things to Note:
▶ To avoid insects and mold, please keep all windows and doors closed. Leaving them open while the AC is on could result in a fee up to $500. For your comfort, we recommend setting the AC between 72-83°F.

▶ This house is privately owned and does not include maid service or daily cleanings. The cleaning fee covers a final cleaning (after your checkout).

▶ Unregistered guests are not permitted.

▶We are happy to accommodate small to medium-sized pets (20–50 lbs, 15–20 inches tall). This guideline helps us maintain cleanliness and protect the condition of the property. A non-refundable pet fee of $125 per pet per stay applies only if noted at booking. If not, we’ll request the fee manually. Pets outside the size range or undeclared may incur a $250 fine.

▶ No parties. Significant noise or playing loud music after 9:00 pm will result in you being asked to leave without a refund for the remaining time of your reservation.

▶ No smoking of any substance is permitted in the unit. Evidence of any type of smoking will result in a $250 fee, and you will be asked to leave without a refund for the remaining time of your reservation.

▶ Check-in is at/after 4 pm and check-out time is no later than 11 am. Early check-in or late check-out is subject to availability. Late check-out without prior approval will result in a fee of $100 per hour for each hour after 11 am.

▶ During check-in, you will find towels, linens, shampoo, conditioner, soap, and toilet paper provided for your convenience. Please note that we do not provide additional supplies during your stay, so we recommend planning accordingly.

▶ Please note that moving the furniture in the house is not permitted. Violation of this rule can result in a penalty in the amount of $250.

▶ Do not flush paper towels, wipes, trash, or feminine products down the toilet. Please use the bins instead. If it is found that something has been flushed and clogged the septic system, you could be charged damages.

▶ Our properties are professionally cleaned and treated regularly for pests. Due to the local climate, occasional insects may enter the home despite our best efforts. Please let us know if you experience any issues, and we’ll address them immediately.

Interaction with Guests:
》 We are available to assist you with any questions or inquiries you may have. Feel free to reach out to us prior to booking, and we'll be more than happy to provide you with any additional information you need to ensure a pleasant stay.

Guest Reviews:

- "First of all Irina was a great communicator, place nice and clean, very simple check in and out. I have to extend for 2 more days and She was very helpful. 5 stars for sure. " - "Place and yard are perfect size for having a dog but the trash bins where full and there was glass and debris of wood with nails in the ground. Looked bigger in the pictures but nice and comfy." - "Nice place, not far from Rollins college and good price, I surely recomend it."

Apartments in Winter Park
Just 3 Blocks to Park Ave Shops/Restaurants, 2 From The Winter Park Village!
Apartment
Winter Park, Florida, USA

Modern, clean and unique. Second floor penthouse unit overlooking the pool area. Gorgeous acacia wood floors, quartz counter tops, high-end cabinetry and fixtures, great new furnishings and mattresses, 8' solid core interior doors, high 10' ceilings, spacious open layout with a balcony offering fantastic sunset views and more! This property gets high ratings for very good reasons; come see! If you haven't explored Winter Park's Park Avenue, then you must!

Salt water heated pool and hot tub. 2 covered parking spaces one uncovered, beautiful acacia wood floors, front load Miele washer/dryer in apartment, grill station poolside, travertine pool deck, 185 square foot covered balcony and beautiful grounds.

Luxury apartments built with quality and comfort in mind. Make your stay stylish, uplifting and comfortable.

Light, bright and full of delight! Just three blocks from Park Ave.'s numerous shops, restaurants and bars, two from The Winter Park Village's shops, restaurants and bars and 2/3 mile to Rollins campus. Simple elegance in downtown Winter Park defined by contemporary design and leisurely living. Publix supermarket two blocks, Whole Foods one half mile, and Trader Joe's three quarter mile away! Convenience is at your doorstep.

Guest Reviews:

- "Large condo, friendly neighbors, nicely decorated, good location." - "Large, airy and nicely appointed apartment. Owner lives on site and is extremely accessible and cooperative. Loved location. My wife and I are planning to return." - "We enjoyed our 5 weeks in Winter Park. Space was great — especially loved the open living area and balcony with afternoon sun. Master bedroom is huge and other 2 bedrooms very comfortable. Host was very accommodating when I asked if the unit had a desk he purchased one prior to my arrival. Convenient location that is walking distance to shops and restaurants and the Saturday farmer’s market. Hope to return next year. One note that the photos show lounge type seating on the balcony but it is actually a table and chairs that was great for meals and games outside."

Apartments in Winter Park
Cozy 1BR Duplex|Winter Park|Close to Attractions
Apartment
Winter Park, Florida, USA

Summary:
Delve into a serene retreat in the heart of Winter Park!
✦ Cozy 1-bedroom duplex with top-notch amenities.
✦ Nestled amidst galleries, theaters, and Orlando's major attractions.
✦ Perfect for couples or a small group up to 3.
Book now! Click the "♡ Save" to bookmark this gem and get exclusive deals.

The Space:
We are excited to share our haven with travelers from all over. Our mission is to offer you the most delightful stay, filled with rest and recreation, so you can create cherished moments.

This warm apartment is crafted for convenience and relaxation:

✦ 1 BEDROOM ✦
Peacefully designed to cater to your rest needs.
✔︎ Bedroom: King bed

✦ LIVING ROOM ✦
The heart of the home, perfect for unwinding.
✔︎ TV
✔︎ Trundle Twin Daybed (Sofa)
✔︎ Seats

✦ KITCHEN & DINING ✦
A modern kitchen space for your culinary desires.
✔︎ Dining table to host delightful meals
✔︎ Fully-equipped with cookware and essentials

✦ 1 BATHROOM ✦
Well-appointed and stocked for your comfort.
✔︎ Shower
✔︎ Essential toiletries
✔︎ Towels

✦ OTHER AMENITIES ✦
✔︎ High-speed Wi-Fi
✔︎ On-site parking
✔︎ Washer & Dryer

Guest Access:
✔︎ Guests enjoy complete access to the entire apartment, ensuring utmost privacy.
✔︎ Use of kitchen, high-speed Wi-Fi, and indulge in cable TV entertainment.
✔︎ On-site free parking for your convenience.

Getting Around:
Exploring Winter Park and Orlando's attractions is a breeze from our location.

✦ By Car: Most major attractions are a short drive away:
Full Sail ➠ 2 min
Baldwin Park ➠ 5 min
Park Ave ➠ 8 min
UCF ➠ 10 min
MCO Airport ➠ 20 min
Universal Studio ➠ 25 min
Sea World ➠ 25 min
Disney World ➠ 30 min

✦ On Foot: Wander and discover nearby galleries, theaters, parks, and eateries.
✦ Public Transport: Convenient bus lines connect you to Orlando's spots.
✦ Ride-Sharing & Taxis: Uber, Lyft, and local taxis are a call away.

Whether you're here to explore the artsy enclaves of Winter Park or dive into the adventures Orlando offers, our duplex promises a restful home base.

Other Things to Note:
ARRIVAL & DEPARTURE:
• For check-in, door code will be provided.
• Any unapproved late check-outs may result in fee.

AMENITIES:
• On arrival, the condo is furnished with essential amenities for your comfort.
• Kindly note, amenities are not replenished during your stay.

HOUSEKEEPING:
• We respect your privacy; daily housekeeping services aren't available.
• A cleaning fee is applied for post-departure servicing.

PEACE & RESPECT:
• Pets are welcome based on our guidelines.
• Events or parties are not permitted on the premises.
• Smoking and drugs on the property are strictly prohibited.

PARKING GUIDELINES:
• Free Parking on Street available for your vehicles

House Rules

▶ To avoid insects and mold, please keep all windows and doors closed. Leaving them open while the AC is on could result in a fee up to $500. For your comfort, we recommend setting the AC between 72-83°F.

▶ This house is privately owned and does not include maid service or daily cleanings. The cleaning fee covers a final cleaning (after your checkout).

▶ Unregistered guests are not permitted.

▶We are happy to accommodate small to medium-sized pets (20–50 lbs, 15–20 inches tall). This guideline helps us maintain cleanliness and protect the condition of the property. A non-refundable pet fee of $125 per pet per stay applies only if noted at booking. If not, we’ll request the fee manually. Pets outside the size range or undeclared may incur a $250 fine.

▶ No parties. Significant noise or playing loud music after 9:00 pm will result in you being asked to leave without a refund for the remaining time of your reservation.

▶ No smoking of any substance is permitted in the unit. Evidence of any type of smoking will result in a $250 fee, and you will be asked to leave without a refund for the remaining time of your reservation.

▶ Check-in is at/after 4 pm and check-out time is no later than 11 am. Early check-in or late check-out is subject to availability. Late check-out without prior approval will result in a fee of $100 per hour for each hour after 11 am.

▶ During check-in, you will find towels, linens, shampoo, conditioner, soap, and toilet paper provided for your convenience. Please note that we do not provide additional supplies during your stay, so we recommend planning accordingly.

▶ Please note that moving the furniture in the apartment is not permitted. Violation of this rule can result in a penalty in the amount of $250.

▶ Do not flush paper towels, wipes, trash, or feminine products down the toilet. Please use the bins instead. If it is found that something has been flushed and clogged the septic system, you could be charged damages.

Interaction with Guests:
We are available to address any questions. Do not hesitate to contact us prior to your reservation for any details to guarantee a seamless and peaceful stay.

Guest Reviews:

- "We had great time. No problems what so ever with the room." - "We needed a place for 2 people and dogs. This property has a huge fenced in yard and was perfect for our fur babies! House was clean and cozy!"

Apartments in Winter Park
Three Blocks to Park Ave, 2 Blocks to WP Village!
Apartment
Winter Park, Florida, USA

Great Location! If you haven't explored Winter Park's Park Avenue, then you must! Three blocks to Park Ave and two blocks to the Winter Park Village! Cozy and modern space. Outdoor grill and bikes for your enjoyment. Enjoy the convenience and tranquility of one of Florida's greatest walking communities while residing in style and sophistication. Heated pool and hot tub! The pool, hot tub and grill stations are shared. Fastest internet speed available: 139MBPS download and 21.5 MBPS upload!

Guest Reviews:

- "Location, Location, Location.. A 10 min walk to Park Avenue. And a heated pool steps outside our kitchen door. We have already booked for next winter 😜" - "it was very nice and close to everything. the apartment was beautiful." - "Property is upscale, pretty pool area, great management, convenient to downtown Winter Park."

Apartments in Winter Park
Cabana style studio apt/private garden near Rollins and Park Ave. 1 week minim
Apartment
Winter Park, Florida, USA

About this space
Cook in or don't in this private and luxurious yet serene studio, where fun mid century meets old florida and cabana style. All furnishings are interior designer specified. It has plenty of basic cooking supplies and ample closet and bathroom storage. Luxe quality bedding. The back wall is papered in handmade papers to provide a soothing natural texture to contrast with the glossy turquoise floors. It has a tropical private garden for eating. our minimum booking time is 28 days.
Guest access
Private studio guest house and garden.
Other things to note
I welcome constructive criticism and ideas. I also love giving activity and dining recommendations.

Guest Reviews:

- "Had a very nice stay in Winter Park this weekend. Host was gracious and attentive." - "Wonderful hosts are available anytime with very helpful knowledge of the entire area. Love the neighborhood- perfect for walking around lovely tree lined streets. Close (easy 5 minute walk) to downtown Winter Park with all the great shops! We would love to come back!!!"

Apartments in Winter Park
Walk To Park Ave, Heated Pool, Hot Tub, Grill Station, Modern and Comfortable!
Apartment
Winter Park, Florida, USA

This is a downstairs end apartment with a back door that opens directly onto the pool deck near the hot tub. The apartment has wood floors, high ceilings, great furniture, fixtures and finishes and the kitchen has everything you need to prepare meals etc.
Excellent location! Just two blocks to the Winter Park Village and 3 to Park Ave.

Guest Reviews:

- "Christopher is an excellent host. We enjoyed the location and walking to Park Avenue restaurants."

Apartments in Winter Park
LUXURY AND LOCATION!
Apartment
WINTER PARK, Florida, USA

Great Location! If you haven't explored Winter Park's Park Avenue, then you must! Three blocks to Park Ave and two blocks to the Winter Park Village! Cozy and modern space. Heated pool, outdoor grill and bikes for your enjoyment. Enjoy the convenience and tranquility of one of Florida's greatest walking communities while residing in style and sophistication. Heated pool and hot tub! The pool and hot tub! Fastest internet speed available: 139MBPS download and 21.5 MBPS upload!

Amenities:

Kitchen • Child Friendly • Fireplace/Heating • Accessibility • Bedding/Linens • Tv • Balcony/Terrace • Laundry • Pool • Security/Safety • Internet • Pet Friendly

Apartments in Winter Park
You're Pampered Here - Just 3 Blocks From Park Avenue!
Apartment
Winter Park, Florida, USA

Modern, clean and unique. Fastest internet speed available: 139MBPS download and 21.5 MBPS upload! Second floor penthouse unit overlooking the pool area. Gorgeous acacia wood floors, quartz counter tops, high-end cabinetry and fixtures, new furnishings and mattresses, 8' solid core interior doors, high ceilings, spacious open layout with a balcony offering fantastic sunset views and more! If you haven't explored Winter Park's Park Avenue, then you must!

Guest Reviews:

- "This was our second visit to this property and we will be back. The property is well located near town, an easy walk to shops and restaurants. The unit is well equipped and matches the online description. Check in was easy and the host was very responsive to all questions and requests. We had lots of hot weather and the pool was a big bonus."

Apartments in Winter Park
Luxury Living Just 3 Blocks From Park Ave!
Apartment
WINTER PARK, Florida, USA

Beautiful Acacia wood flooring, with marble in the bathrooms and porcelain tile in the kitchen. Quartz countertops, ceilings are 10 feet high and there is a balcony with two sliding glass doors going to it from the master bedroom and living/family room. Very open floor plan. There is 1114 square feet of space inside, but it feels larger than that. Beautiful furnishings including an Italian leather couch. Large TV in the living room with the fastest WiFi available in the area - Hulu is programmed into the TV as the source for live TV. It is an upstairs apartment, top floor, 2. Shared with nine other apartments is a beautiful heated salt water pool, hot tub and grilling station. The apartment comes with one dedicated parking space right at the base of the stairs and there are plenty of additional spaces in the rear parking lot.

Guest Reviews:

- "My husband and I spent a month on the property working remotely and visiting with family. The condo is small but we were able to find places for each to work. We did have some issues with spotty WiFi connections and the host responded quickly but never was able to resolve the issue. The location was within walking distance to many restaurants and bars as well as a handy mall with grocery shopping. Other tenants were friendly and had small dogs like ours so felt right at home. We appreciated our host’s flexibility in scheduling our stay as well."

Apartments in Winter Park
Little gem apartment
Apartment
Winter Park, Florida, USA

You'll fall in love with this little gem located in the heart of Winter Park. Filled with charming vintage furniture and homey trimmings. This one bedroom/one bathroom apartment has all you need in size and trimmings. Comfortable sitting area with flat screen smart TV, cozy dining at the kitchen bar or on the shaded, private and peaceful terrace. Don't let the size fool you, the fully equipped kitchen is mighty impressive!

Don't forget to venture out and walk to the core of the lovely Winter Park. This cottage is located 0.4 miles from Park Ave, 0.7 from Central Park with its Saturday Farmers Market and bi-annual Art Festival and 0.9 miles from the Charles Hosmer Morse Museum of American Art.

Amenities:

Wellness Facilities • Bedding/Linens • Kitchen • Internet • Barbecue/Outdoor Cooking • Air Conditioner • Laundry • Fireplace/Heating • Security/Safety • Other • Parking • Pet Friendly

Apartments in Winter Park
Cozy and Chic Winter Park Studio which is conveniently located just for you
Apartment
Winter Park, Florida, USA

Light, airy, and perfectly appointed studio. Enjoy this fully furnished and centrally-located location. This space provides an ideal home away from home that we have curated with comfort in mind. Enjoy sunny days on the private deck and cozy nights in luxury! This memorable studio is the perfect home base for your trip to Winter Park. Nestled in a beautiful and soothing setting, this gorgeous property offers everything you need for a comfortable stay. With a cozy bedroom, you'll have a peaceful retreat to relax after a day of exploring. The property is equipped with all the essentials, including a hair dryer, AC, WiFi, heating, iron, and washing machine. Whether you're here for a weekend getaway or an extended stay, our studio provides a tranquil and inviting atmosphere. It's easy to see why you'll be able to unwind at our place. You'll have a relaxing time overlooking your own private deck.

Amenities:

Balcony/Terrace • Fireplace/Heating • Other • Pet Friendly • Laundry • Security/Safety • Kitchen • Air Conditioner • Tv • Internet • Parking • Bedding/Linens

Winter Park Family Friendly Apartments

Winter Park Pet Friendly Apartments

Winter Park Apartments with Parking

Winter Park Apartments with Entertainment

Winter Park Apartments on the Map

Compare the Best Apartments in Winter Park – Addresses, Prices, Stars, Rating, and Review Count

Property Name Address Price ($) Star Rating Review Count Book
1BR 1BA in Historic Park Ave Home 1645 North Park Avenue, Orlando, FL, FL 32789, USA 131 4.0 10.0 6 Click here
College quater charming Winter Park Historic Dist Rollins College quarters Winter Park, Florida, USA 99 2.0 9.0 2 Click here
Quiet Location Duplex House - Minutes Away from Everything - Winter Park, Florida 5030 Oak Hill Drive, Orlando, FL, FL 32792 134 3.0 7.6 30 Click here
Charming 2-bedroom apartment with AC and WiFi in enchanting Winter Park Winter Park, Florida, USA 77 2.0 1 Click here
Charming CozyLux 2-bedroom apartment Winter Park, Florida, USA 194 2.0 1 Click here
Mid Century Luxury, 1 block from Park Ave (#3) Winter Park, Florida, USA 163 10.0 27 Click here
Modern apartment with enclosed yard, central AC, & kitchenette - dog-friendly Winter Park, Florida, USA 181 9.8 27 Click here
Mid Century Luxury, 1 block from Park Ave (#2) Winter Park, Florida, USA 161 10.0 22 Click here
Adorable 1 Bedroom in the perfect location! Winter Park, Florida, USA 82 9.2 7 Click here
Cozy Winter Park 2BR with Garden & Full Kitchen Winter Park, Florida, USA 156 7.6 7 Click here
Just 3 Blocks to Park Ave Shops/Restaurants, 2 From The Winter Park Village! Winter Park, Florida, USA 3361 10.0 4 Click here
Cozy 1BR Duplex|Winter Park|Close to Attractions Winter Park, Florida, USA 128 7.4 3 Click here
Three Blocks to Park Ave, 2 Blocks to WP Village! Winter Park, Florida, USA 157 9.4 3 Click here
Cabana style studio apt/private garden near Rollins and Park Ave. 1 week minim Winter Park, Florida, USA 136 10.0 2 Click here
Walk To Park Ave, Heated Pool, Hot Tub, Grill Station, Modern and Comfortable! Winter Park, Florida, USA 144 10.0 1 Click here
LUXURY AND LOCATION! WINTER PARK, Florida, USA 163 10.0 1 Click here
You're Pampered Here - Just 3 Blocks From Park Avenue! Winter Park, Florida, USA 238 10.0 1 Click here
Luxury Living Just 3 Blocks From Park Ave! WINTER PARK, Florida, USA 286 8.0 1 Click here
Little gem apartment Winter Park, Florida, USA 102 1 Click here
Cozy and Chic Winter Park Studio which is conveniently located just for you Winter Park, Florida, USA 116 1 Click here

Note: The prices for each Apartments in Winter Park do vary. This can be because of the number of people you are booking for, how far in advance you book and the season. The prices above are only meant as a rough estimate for comparison purposes. Click the buttons above (or click here) to get the latest prices.

Frequently Asked Questions

Serviced apartments in Winter Park with pool access include:

  • 1BR 1BA in Historic Park Ave Home.- Review Count: 6, Rating: 10.0
  • Adorable 1 Bedroom in the perfect location! .- Review Count: 7, Rating: 9.2
  • Just 3 Blocks to Park Ave Shops/Restaurants, 2 From The Winter Park Village!.- Review Count: 4, Rating: 10.0

Family-friendly apartments in Winter Park include:

  • College quater charming Winter Park Historic Dist Rollins College quarters.- Review Count: 2, Rating: 9.0
  • Quiet Location Duplex House - Minutes Away from Everything - Winter Park, Florida.- Review Count: 30, Rating: 7.6
  • Charming CozyLux 2-bedroom apartment .- Review Count: 0, Rating: 0.0

Pet-friendly apartments in Winter Park include:

  • Quiet Location Duplex House - Minutes Away from Everything - Winter Park, Florida.- Review Count: 30, Rating: 7.6
  • Charming 2-bedroom apartment with AC and WiFi in enchanting Winter Park.- Review Count: 0, Rating: 0.0
  • Modern apartment with enclosed yard, central AC, & kitchenette - dog-friendly.- Review Count: 27, Rating: 9.8

Apartments in Winter Park with on-site parking include:

  • 1BR 1BA in Historic Park Ave Home.- Review Count: 6, Rating: 10.0
  • Quiet Location Duplex House - Minutes Away from Everything - Winter Park, Florida.- Review Count: 30, Rating: 7.6
  • Mid Century Luxury, 1 block from Park Ave (#3).- Review Count: 27, Rating: 10.0

Some of the best Apartments in Winter Park are:

  • 1BR 1BA in Historic Park Ave Home.- Review Count: 6, Rating: 10.0
  • Quiet Location Duplex House - Minutes Away from Everything - Winter Park, Florida.- Review Count: 30, Rating: 7.6
  • College quater charming Winter Park Historic Dist Rollins College quarters.- Review Count: 2, Rating: 9.0

Some of the popular Apartments in Winter Park are:

  • Quiet Location Duplex House - Minutes Away from Everything - Winter Park, Florida.- Review Count: 30, Rating: 7.6
  • Mid Century Luxury, 1 block from Park Ave (#3).- Review Count: 27, Rating: 10.0
  • Modern apartment with enclosed yard, central AC, & kitchenette - dog-friendly.- Review Count: 27, Rating: 9.8