Best Short-Term Rentals in Winter Park

Located in Winter Park, Florida, this hotel offers free WiFi and an outdoor pool. Rollins College is located 2133 feet from the property. Park Avenue, where guests can shop and dine, is 2461 feet away. A refrigerator and coffee-making facilities are provided in each room at Winter Park’s The Alfond Inn. A cable TV and iPod docking station are also featured. The private bathroom includes a hairdryer. A fitness center, a business center, and laundry facilities are available at The Alfond Inn for guests’ convenience. A daily maid service and a 24-hour front desk are also provided. Hamilton’s Kitchen at The Alfond Inn serves southern-style cuisine for breakfast, lunch, and dinner as well as weekend brunch. The on-site restaurant offers a full service bar as well. The Charles Hosmer Morse Museum of American Art is 2 minutes’ drive from the hotel. Winter Park Country Club, a public golf course, is 3117 feet away. Harry P Leu Gardens is 12 minutes’ drive from The Alfond Inn.

- "Excellent stay & the staff was incredibly!" - "Excellent! We’ll do it again." - "One of the best hotels I have ever stayed" - "Great sleep" - "Can't wait to return" - "Excellent hotel and great staff." - "Amazing place to stay!" - "Art lovers would really enjoy this high end, art filled boutique hotel." - "Best hotel in Winter Park" - "Unassuming excellence with exceptional service" - "The Alfond Inn is a delightful hotel and I look forward to staying there again."

Tuscan-style hotel with a fitness center and a steam room
An outdoor pool, a restaurant, and a fitness center are available at this smoke-free hotel. WiFi in public areas is free. Additionally, a bar/lounge, a poolside bar, and a steam room are onsite.
The Alfond Inn offers 112 accommodations with safes and coffee/tea makers. Pillowtop beds feature premium bedding. 55-inch flat-screen televisions come with premium cable channels. Bathrooms include bathtubs or showers, bathrobes, slippers, and designer toiletries.

Guests can surf the web using the complimentary wireless Internet access. Business-friendly amenities include desks and phones; local and long-distance calls are complimentary (restrictions may apply). Additionally, rooms include hair dryers and irons/ironing boards. Housekeeping is provided daily.

- "Very clean and modern." - "Great hotel for adults! Awesome art collection and overall great experience. " - "Amazing property with" - "Excellent, staff A plus" - "Always a fantastic stay. Clean rooms, beautiful grounds, great amenities. Close to everything. We stayed here for our wedding and had our reception at Hamiltons Kitchen. It's always great to come back." - "This is a really nice hotel. very convenient and walking distance to Rollins and downtown Winter Park"

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.

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

Hotel with a restaurant, steps from Winter Park History Museum
This smoke-free hotel features a restaurant, a bar/lounge, and a 24-hour business center. WiFi in public areas is free. Other amenities include a coffee shop/cafe, valet parking, and coffee/tea in a common area.
Park Plaza Hotel offers 28 accommodations with complimentary newspapers and complimentary bottled water. Each accommodation is individually furnished and decorated. Tempur-Pedic beds feature Egyptian cotton sheets, down comforters, and premium bedding. Flat-screen televisions come with premium cable channels. Bathrooms include shower/tub combinations, complimentary toiletries, and hair dryers.

This Winter Park hotel provides complimentary wireless Internet access. Business-friendly amenities include desks and phones; local and long-distance calls are complimentary (restrictions may apply). Housekeeping is offered daily and irons/ironing boards can be requested.

- "Quaint establishment in a wonderful location." - "A bit too old, but classic at the same time" - "The hotel is full of character. If you are looking for updated and modern this is not your place, but if you enjoy eclectic character, historic features, kind employees, friendly atmosphere in a great location this is the best place a round. I would absolutely stay here again. In fact I can’t wait too! The staff was accommodating and went above and beyond. The rooms are old but that is part of what you are paying for in my opinion. They even supply ear plugs if you are concerned about the train. "

The Winter Park Experience offers accommodations in Orlando, 7.6 miles from Kia Center and 7.7 miles from Church Street Station. This property offers access to a patio and free private parking. Outdoor seating is also available at the vacation home. With free Wifi, this 3-bedroom vacation home features a flat-screen TV, a washing machine, and a fully equipped kitchen with a dishwasher and oven. Towels and bed linen are available in the vacation home. For added privacy, the accommodation features a private entrance. The vacation home has a picnic area where you can spend the day outdoors. Camping World Stadium is 8.8 miles from The Winter Park Experience, while Addition Financial Arena is 10 miles from the property. Orlando Sanford International Airport is 14 miles away.

- "Despite what I expressed in the previous question, the stay was excellent." - "Charming and clean house convenient to everything in Winter Park" - "Beautiful Winterpark location"

Hotel in Winter Park with a fitness center and a 24-hour business center
A restaurant, a fitness center, and a bar/lounge are available at this smoke-free hotel. Free WiFi in public areas and free self parking are also provided. Other amenities include a 24-hour business center, a business center, and a 24-hour front desk.
Hilton Garden Inn Winter Park offers 102 air-conditioned accommodations with laptop-compatible safes and coffee/tea makers. Flat-screen televisions are featured in guestrooms. Bathrooms include bathtubs or showers and hair dryers.

This Winter Park hotel provides complimentary wireless Internet access. Business-friendly amenities include desks, desk chairs, and phones.

- "Clean, good breakfast options, friendly staff." - "Definitely staying here again. " - "Nice clean and quiet rooms property is close to so many dining options " - "Amazing room amenities and super quiet! Staff was amazing at check-in, check-out, and dining/bar. " - "Liked it was like new. Breakfast was good (for a price) except for the limp toast. " - "Great property! Loved the convenience of it" - "For all the reasons mentioned above."

Charming Winter Park - Express offers accommodations in Orlando, 7.1 miles from Spectrum Stadium and 11 miles from Church Street Station. The air-conditioned accommodation is 6.7 miles from Addition Financial Arena. The accommodation offers a 24-hour front desk and free Wifi is available throughout the property. The spacious vacation home has 2 bedrooms and 1 bathroom with free toiletries. Towels and bed linen are offered in the vacation home. For added privacy, the accommodation features a private entrance. Kia Center is 11 miles from the vacation home, while Camping World Stadium is 13 miles from the property.

Air Conditioner • Security/Safety • Guest Services • Pet Friendly • Internet

Hotel in Winter Park with free breakfast and a fitness center
Along with a fitness center, this hotel has a bar/lounge and a snack bar/deli. Free continental breakfast and free WiFi in public areas are also provided. Other amenities include self parking, coffee/tea in a common area, and dry cleaning.
Housekeeping is available on request.
SpringHill Suites by Marriott Winter Park offers 126 air-conditioned accommodations with iPod docking stations and coffee/tea makers. Accommodations have separate sitting areas and are furnished with twin sofa beds. Pillowtop beds feature premium bedding. A pillow menu is available. 45-inch Smart televisions come with premium cable channels and Netflix. Bathrooms include showers with rainfall showerheads, and hair dryers.

This Winter Park hotel provides complimentary wireless Internet access, with a speed of 100+ Mbps (good for 1–2 people or up to 6 devices). Business-friendly amenities include desks and desk chairs, as well as phones; free local calls are provided (restrictions may apply). Additionally, rooms include irons/ironing boards and fans. Change of towels and change of bedsheets can be requested. Housekeeping is provided daily.

The recreational activities listed below are available either on site or nearby; fees may apply.

- "Nice and spacious rooms " - "It was extremely convenient while in town doing business." - "Great facilities at this price. Very clean and comfortable. Very helpful staff." - "The place was spotless. The room and lobby area were spacious. The room was well appointed. " - "Everything was great. Good free breakfast. Clean and spacious rooms." - "This hotel was very clean and quiet. I could not hear any of the adjoining rooms or foot traffic in the halls. Very nice experience."

Offering free WiFi, this Winter Park, Florida hotel is 1148 feet from Rollins College. Historic Winter Park, featuring shops and restaurants, is right outside your door. Just step out of our Hotel onto upscale Park Avenue! A cable TV is featured in all Park Plaza Hotel rooms. An private bathroom with a bath or shower is also included in addition to in-room air conditioning and heating. A 24-hour front desk and valet parking are available for guests’ convenience. The hotel also provides laundry and dry cleaning services, a business center, and a safety deposit box. Winter Park Amtrak is 1640 feet from the Park Plaza Hotel, and The Charles Hosmer Morse Museum of American Art is 1969 feet away. Universal Studios Orlando is 23 minutes’ drive away.

- "Excellent place to stay for a girl's getaway." - "Fun." - "Not as enjoyable as last time" - "The property is over 140 yrs old. It is so unique. A lot of the original frame work, etc are there" - "Hotel is ideally located, pleasant staff, has some old time charm but ultimately too worn and cramped for a return visit" - "Disappointing"

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

- "This is truly a home away from home. We loved our stay. The screened on porch is a cocktail haven. The beautiful fenced in yard a super bonus. You can walk anywhere - to nature, museums, bars, bakeries, the thrifty, park ave...the bank where ever. Loved it so much! Thank you Tony for sharing your lovely space."

Hilton Garden Inn Winter Park, FL features a fitness center, shared lounge, a restaurant and bar in Orlando. This 3-star hotel offers room service, a 24-hour front desk and free WiFi. Camping World Stadium is 6.7 miles from the hotel and Holy Land Experience is 11 miles away. At the hotel, all rooms come with a desk. Each room is equipped with air conditioning and a TV, and certain rooms at Hilton Garden Inn Winter Park, FL have a safety deposit box. Guest rooms will provide guests with a fridge. The breakfast offers buffet, à la carte or continental options. Kia Center is 5.5 miles from the accommodation, while Church Street Station is 6.3 miles away.

- "My little dog & I stayed to help my daughter move in next door" - "/" - "Just right for our one dayvisit to spend time with family in the area." - "Very convenient, clean and modern hotel." - "Overall it was fine." - "The service was excellent and the accomodations were good." - "Lovely Christmas time with Family" - "Very nice place to stay , but need to fix the parking problem" - "Great place and excellent value for money!"

You'll find the convenience of laundry facilities available during your stay.

Parking • Wellness Facilities • Laundry • Child Friendly

Located in Orlando, 6.5 miles from Kia Center, SpringHill Suites by Marriott Winter Park has accommodations with a garden, private parking, a shared lounge and a terrace. Among the facilities of this property are a restaurant, a 24-hour front desk and an ATM, along with free WiFi throughout the property. Guests can have a drink at the snack bar. Guests at the hotel can enjoy a buffet breakfast. You can play tennis at this 3-star hotel, and the area is popular for hiking and fishing. There's an in-house bar and guests can also use the business area. Church Street Station is 6.5 miles from SpringHill Suites by Marriott Winter Park, while Camping World Stadium is 7.7 miles from the property.

- "Nice Stay" - "good location to stay when we are in town visiting family and firends" - "Great Stay, will stay again." - "This Springhill suites has a fabulous staff." - "My stay was cozy." - "Very nice" - "The service was excellent and the accomodations were good." - "enjoyed and I’ll be back!" - "The service was excellent and the accomodations were good." - "Great rooms, good breakfast, comfy beds, friendly staff!"

Hotel in Winter Park with an outdoor pool
An outdoor pool, self parking, and free WiFi in public areas are available at this hotel.
Gorgeous property at winter park -131 offers 20 accommodations with irons/ironing boards. These individually decorated and furnished accommodations have separate dining areas. Guests can surf the web using the complimentary wireless Internet access (speed: 250+ Mbps (good for 3–5 people or up to 10 devices)).
Recreational amenities at the hotel include an outdoor pool.

Internet • Parking • Laundry • Pool • Restaurant • Child Friendly • Other

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.

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

Private 2 bedroom guest suite with its own entry and a separate sitting room. Tandem bedroom include 1 queen sized bed and bunk beds. Easily sleeping 4. We are located very close to downtown Winter Park and steps off Park Ave. Museums, restaurants, golf and shopping are all within walking distance. There is a dedicated desk/work area for corporate guest. Designed to feel like home away from home we want to make sure your stay with us is enjoyable.

- "This is a charming little place with close proximity to the Winter Park restaurants, museums, shopping and scenic boat tours. Also just 15 minutes to downtown Orlando. It was also very quiet for working at the desk and sleeping at night. The mini fridge, microwave and coffee maker allowed me to make a simple breakfast and lunch. Michelle the host provided excellent communications." - "Great option for a stay in Winter Park. Very nice place for a family, quiet, great location, helpful owners and a comfortable home with everything you need."

Spacious Modern Japandi Retreat - Winter Park offers accommodations in Orlando, 10 miles from Addition Financial Arena and 10 miles from Spectrum Stadium. This property offers access to a balcony and free private parking. Church Street Station is 11 miles away and Kia Center is 11 miles from the vacation home. With free Wifi, this 1-bedroom vacation home offers a flat-screen TV, a washing machine, and a fully equipped kitchen with an oven and toaster. The accommodation is non-smoking. Camping World Stadium is 12 miles from the vacation home, while Holy Land Experience is 15 miles away. Orlando International Airport is 15 miles from the property.

Parking • Internet • Security/Safety • Barbecue/Outdoor Cooking • Pet Friendly • Child Friendly • Air Conditioner

You'll fall in love with this beautiful historic cottage located in the heart of Winter Park. Filled with charming vintage furniture and homey trimmings. Dine in the luminous sunroom, enjoy a cup of tea or a movie in the warm and inviting living room. Two welcoming bedrooms with DreamCloud mattresses and luxurious linens will ensure you a restful night sleep. Don't let the size fool you, the fully equipped kitchen is mighty impressive! The outdoor deck sheltered by the old oak tree is shaded, private and peaceful.
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.

Don't hesitate to reach out if you would like to book our cottage for a shorter stay. I will be happy to try to accommodate your needs.

- "Absolutely loved my stay ~ darling home in historical neighborhood. Walking distance to Park Avenue through charming college area. So many things to do nearby. Walkable to everything! Owners were amazing + great communication. Thanks for a wonderful experience!" - "Loved this spot, walking distance to everything we needed in town and on campus, cant wait to come" - "Charming cottage located close to Park Ave and Rollins College campus."

Prvt 8 guests, pool, Disney, Universal offers accommodations in Orlando, 8.6 miles from Addition Financial Arena and 9 miles from Spectrum Stadium. This property offers access to a terrace, a pool table, free private parking, and free Wifi. The vacation home offers an outdoor swimming pool and private check-in and check-out. The air-conditioned vacation home consists of 4 bedrooms, a living room, a fully equipped kitchen with a dishwasher and a coffee machine, and 3 bathrooms with a walk-in shower and a hair dryer. Towels and bed linen are offered in the vacation home. The property has an outdoor dining area. Church Street Station is 10 miles from the vacation home, while Kia Center is 10 miles from the property. Orlando International Airport is 14 miles away.

- "acceptable accommodation, attentive host, room for improvement"

Entire Private Home -
2 bed 2 bath fully furnished unit located just one block from Park Ave in Winter Park. ***Several units are available in the same building so please inquire for accurate availability***

- "Wonderful" - "We loved this place and will stay again! Clean, responsive, efficient. They brought us what we needed when we needed it, and the manager was super nice on the phone for everything! Loved the modern, clean feel. It was such a great stay and a great location- very walkable. My kids and our family had a great time. Highly recommend! Will likely stay again next time I am in town for work. :)" - "Great condo, walked all over down at the lake. No problems with neighbors No problems at all."