Winter Park Vacation Home Rentals from CA $214: Search Top Private Vacation Homes for Rent

A two-story house with a balcony, surrounded by lush greenery and trees.

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Our top choices for Winter Park vacation homes

A modern kitchen with a marble countertop, built-in appliances, and a dining area with a green sofa.

1. Funky Remodeled Otown Bungalow Sleeps 8

Fairview Shores

Julia K.

CA $360 total

includes taxes & fees

Nov 22 - Nov 23

A modern kitchen with white cabinets, a wooden dining table set with white plates and a knife, and a potted plant.

2. Cozy home 5min to Park Ave and Downtown Orlando

Fairview Shores

tyson s.

CA $397 total

includes taxes & fees

Nov 30 - Dec 1

A modern kitchen with stainless steel appliances, a grey sofa, and a dining area with a floral rug.

3. Charming home @wp. Patio +Gazebo. close to highwys

Fairview Shores

Vicki V.

CA $359 total

includes taxes & fees

Nov 17 - Nov 18

A modern kitchen with dark wooden cabinets, a stainless steel refrigerator, a microwave, and an oven.

4. Mills House @WP. Sleeps 11 Renovated. Queen beds

Fairview Shores

Larry S.

CA $440 total

includes taxes & fees

Nov 17 - Nov 18

A modern living room with hardwood flooring, a grey sofa, a glass coffee table, and a kitchen area with wooden cabinets and a stainless steel refrigerator.

5. 3-bedroom house in quaint Winter Park with cool vibes

Hannibal Square

CA $571 total

includes taxes & fees

Dec 7 - Dec 8

A modern kitchen with white cabinets, a stainless steel refrigerator, and a glass dining table with chairs.

6. Spacious 5-bedroom house in gorgeous Winter Park

Winter Park

Hannah F.

CA $431 total

includes taxes & fees

Nov 16 - Nov 17

A living room with a sofa, coffee table, and decorative wall art.

7. Serene Mid-Century 3/2 w/Bonus Room and Huge Shaded Yard w/Fence

Goldenrod

Ashley C.

CA $579 total

includes taxes & fees

Nov 18 - Nov 19

8. Spacious 5-bedroom house in welcoming Winter Park

Winter Park

CA $447 total

includes taxes & fees

Nov 16 - Nov 17

A modern kitchen with dark cabinetry, stainless steel appliances, and a tiled backsplash.

9. Luxury Designer Home • Disney, Universal & Downtown

College Park

Christian H.

CA $890 total

includes taxes & fees

Nov 16 - Nov 17

10. Cute 5-bedroom,6bed house in superb Winter Park.

Winter Park

"We checked in late and were surprised to find half eaten food in the fridge and freezer. Both were very dirty with a noticeable odor. The dishwasher was full of dirty dishes. The oven was full of dirty pans. Most of the dishes in the cupboards had little bits in them as well. There was a fire alarm battery beeping in one of the bedrooms. There was no coffee maker or wine opener or wine glasses or hand soap. There were very few dishes in general, it would have been challenging to cook and serve...

Nyssa S.

CA $431 total

includes taxes & fees

Nov 30 - Dec 1

A modern living room with a dining area, featuring a wooden floor, a gray sofa, a dining table with chairs, and a wall-mounted plant.

11. 2/1 with private backyard in the heart of Ivanhoe

Ivanhoe Village

Josh H.

CA $351 total

includes taxes & fees

Nov 16 - Nov 17

A modern hotel room with a wooden bed, a desk with chairs, a patterned wall, and a window with blinds.

12. Sunshine Escape Guesthouse ☀

Orlando

Robin R.

CA $231 total

includes taxes & fees

Nov 17 - Nov 18

A front door with a glass panel, a wreath, and a doormat with a welcoming message.

13. Cozy, Private, Modern 1BD/1BA Apt in College Park Home. Pet Friendly!

College Park

Kevin G.

CA $237 total

includes taxes & fees

Nov 16 - Nov 17

A compact room with a bed, a small table with plates, a microwave, and a green wall with a neon sign.

14. CUTE and COZY studio w/ jacuzzi!

Azalea Park

Lindsay W.

CA $243 total

includes taxes & fees

Nov 17 - Nov 18

A hot tub with a waterfall feature, a covered seating area, and a bar with outdoor seating.

15. Private Luxury Pool / Swim up bar / Smart-home

College Park

Mayah Y.

CA $629 total

includes taxes & fees

Nov 16 - Nov 17

A bed with white bedding and two blue pillows with a coral reef design, a tall green plant beside the bed, and a window with grey curtains in the background.

16. Studio in the heart of Orlando

Azalea Park

Matthew

CA $214 total

includes taxes & fees

Nov 30 - Dec 1

A single-story house with a covered porch, a brick pathway leading to the entrance, and a fenced backyard.

17. “The Clementine” Boho Home in Orlando’s Food Scene

Park Lake - Highland

Samuel S.

CA $326 total

includes taxes & fees

Nov 29 - Nov 30

A modern kitchen with a black countertop, two stools, a wooden cabinet, and a TV displaying a mountain landscape.

18. “Downtown Orlando Comfy House”

Lawsona - Fern Creek

Jaqui

CA $384 total

includes taxes & fees

Nov 17 - Nov 18

A modern kitchen with white cabinets, a central island, and a dining area with a table and chairs.

19. Luxury Ranch 2 Master Kg Bed w/ heated Salted Pool

College Park

Tom47 D.

CA $1,194 total

includes taxes & fees

Nov 30 - Dec 1

A bedroom with a bed, a mirror, a wardrobe, and a floral artwork on the wall.

20. Sleeps 8-3 Bedrooms 2 Full Bathroms+Gameroom your perfect vacation home!

Casselberry

Charles T.

CA $326 total

includes taxes & fees

Nov 17 - Nov 18

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Top Winter Park Hotel Reviews

Avanti International Resort

10/10 Excellent

"Great place to stay"

Drury Plaza Hotel Orlando - Disney Springs Area

10/10 Excellent

"My husband and I were just doing one night before we checked in at our Disney resort. We were comparing cost and amenities with the on property Disney resorts. Drury really is a great value, especially if you’re a family of 3 or 4, and you’re having to get everyone fed. It’s an excellent value, beautiful resort, and has excellent amenities. My ONLY complaint was with the pillows. The pillows were terrible. If you like hard pillows, though, you’ll love these. The mattress was great, but the pillows were tough. No complaints otherwise. The staff was amazing, and we e definitely start again—with our own pillows."

Fairfield Inn & Suites Lake Buena Vista in Marriott Village

10/10 Excellent

"The staff were amazing. Ismael at the front desk was training, but was doing a wonderful job. All other front desk staff were also very helpful and very friendly. I truly appreciated that. Breakfast was good, although my partner wanted the diced potatoes every day and they switched out certain items each day."

Evermore Orlando Resort

10/10 Excellent

"We came to celebrate my husband's 60th birthday, just the two of us, and stayed in a beautiful four-bedroom flat. At check-in, I had booked the Bayfront online and initially received a city view we didn't understand the mishap., however the staff let us know there was a complimentary upgrade to the Bayfront, which was wonderful💕 My husband was delighted with the experience. We did need some air freshener in the apartment but otherwise it was clean.👌 The service was excellent. 🥰The staff made my husband feel amazing. surprising him with champagne, and a few appetizers.. They were all so kind and made us feel special. We will definitely return.🌟💕❤️💕"

Find out more about Winter Park

Winter Park Vacation Homes information

Number of reviews	184
Accommodation	5460 Vacation Homes
Lowest Price	CA $214
Highest Price	CA $1,194

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Change your mind

Treat yourself

Be picky

Check prices for these dates

Our top choices for Winter Park vacation homes

1. Funky Remodeled Otown Bungalow Sleeps 8

2. Cozy home 5min to Park Ave and Downtown Orlando

3. Charming home @wp. Patio +Gazebo. close to highwys

4. Mills House @WP. Sleeps 11 Renovated. Queen beds

5. 3-bedroom house in quaint Winter Park with cool vibes

6. Spacious 5-bedroom house in gorgeous Winter Park

7. Serene Mid-Century 3/2 w/Bonus Room and Huge Shaded Yard w/Fence

8. Spacious 5-bedroom house in welcoming Winter Park

9. Luxury Designer Home • Disney, Universal & Downtown

10. Cute 5-bedroom,6bed house in superb Winter Park.