Winter Park Holiday Rentals from NZ$137: Search Short-Term Rentals

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Our top choices for Winter Park holiday rentals

A backyard with a swimming pool, patio furniture, and a covered seating area.

1. Quiet and safe neighborhood come to this great place with lots of room for relax

Orlando

Olubankole S.

includes taxes & fees

16 Nov - 17 Nov

A modern kitchen with stainless steel appliances, a marble island, and pendant lighting.

2. Funky Remodeled Otown Bungalow Sleeps 8

Fairview Shores

Julia K.

includes taxes & fees

22 Nov - 23 Nov

A modern kitchen with white cabinets, stainless steel appliances, and a wooden countertop.

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

Fairview Shores

tyson s.

includes taxes & fees

16 Dec - 17 Dec

A small building with a green door and two vertical light fixtures on either side.

4. Comfy Tiny Home @WP. Large Private Deck+Queen bed

Fairview Shores

includes taxes & fees

23 Nov - 24 Nov

A wooden exterior with a brown door, a black mat at the entrance, and a small plant to the left.

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

Fairview Shores

Vicki V.

includes taxes & fees

17 Nov - 18 Nov

A swimming pool with a brick patio, surrounded by a fence and a building with large windows.

6. 1-bedroom vacation room just 12 minutes from University of Central Florida

Orlando

jamie l.

includes taxes & fees

16 Nov - 17 Nov

A backyard with a grill, patio furniture, and a covered area.

7. OASIS UNDER THE OAK TREE.

Goldenrod

"This is a unique and affordable family opportunity in a residential area close to everything. Military friendly host makes you feel like you are safe with family. Plenty of space for spreading out inside the camper that still provides a private closed off space for quiet time. Less than 10 minutes from Full Sail University for visiting students. I enjoyed the quiet neighborhood and the comfortable living in this very cool urban camping setting. Lots of extras available to hang out in the...

Peg W.

includes taxes & fees

6 Dec - 7 Dec

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.

8. 3-bedroom house in quaint Winter Park with cool vibes

Hannibal Square

includes taxes & fees

7 Dec - 8 Dec

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

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

Fairview Shores

Larry S.

includes taxes & fees

17 Nov - 18 Nov

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

10. Spacious 5-bedroom house in gorgeous Winter Park

Winter Park

Hannah F.

includes taxes & fees

16 Nov - 17 Nov

A modern kitchen with white cabinets, a dining area with a wooden table, and a view of the living room through an archway.

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

Goldenrod

Ashley C.

includes taxes & fees

17 Nov - 18 Nov

12. Spacious 5-bedroom house in welcoming Winter Park

Winter Park

includes taxes & fees

16 Nov - 17 Nov

A modern bathroom with a wooden vanity, a round mirror, and a potted plant.

13. Top 1% Modern Japandi Retreat - Jacuzzi No Fee

Winter Park

Jennifer M.

includes taxes & fees

22 Nov - 23 Nov

A bedroom with a bed, bedside tables, a ceiling fan, a large mirror, and a window with blinds.

14. Luxury Designer Home • Disney, Universal & Downtown

College Park

Christian H.

includes taxes & fees

16 Nov - 17 Nov

15. 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.

includes taxes & fees

30 Nov - 1 Dec

A brick pathway leading through a lush garden with various plants and a statue.

16. Suites by The Wellborn

Lake Cherokee

Wade

includes taxes & fees

29 Nov - 30 Nov

A swimming pool with lounge chairs and palm trees.

17. The Point Hotel & Suites Orlando

Florida Center

Lawana

includes taxes & fees

14 Dec - 15 Dec

A resort pool area with palm trees, lounge chairs, and umbrellas.

18. Marriott's Grande Vista

Orlando

Christina

includes taxes & fees

10 Dec - 11 Dec

A covered patio with wicker furniture and a glass table, overlooking a residential street with houses and palm trees.

19. Stylish & Cozy King Bed Retreat @ Baldwin Park

Orlando

Devan S.

A two-story house with a front porch, a driveway, and a well-maintained lawn.

20. ⛲️Walk to Lake Eola & restaurants

Thornton Park

Al F.

includes taxes & fees

24 Nov - 25 Nov

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Find holiday rentals that suit your style

Top Winter Park Hotel Reviews

A hotel pool area with lounge chairs and umbrellas, surrounded by tall buildings and a sunset sky.

Drury Plaza Hotel Orlando - Disney Springs Area

Lake Buena Vista

10/10 Excellent

Jade

A spacious lobby with a leather sofa, a bar area with stools, and a seating area with tables and chairs.

Embassy Suites by Hilton Orlando Lake Buena Vista South

Kissimmee

10/10 Excellent

Kerryn

Holiday Inn Orlando - I-Drive North by IHG

International Drive District

10/10 Excellent

Srimal

A spacious lobby with a high ceiling, wooden beams, and a central round table surrounded by chairs. There are potted plants, a reception desk, and a wall with a welcome sign.

Hilton Vacation Club Polynesian Isles Kissimmee

Kissimmee

10/10 Excellent

Fantastic place for our 3 weeks for 4 in a 2 bed place. Had 2 bathrooms and excellent kitchen with dishwasher and own laundry. Great staff and easy location to all Disney and Universal at a fraction of the cost of their properties. Apartment was huge and plenty of space. Only cleaned once a week but this was fine as we are used to doing it ourselves and also felt much less intrusive and could just "feel at home". Thanks Polynesian team!

Mark

A hotel room with a bed, bedside table, lamp, and a view of the sky through a window.

Hyatt House Orlando International Drive

International Drive District

10/10 Excellent

Holly

A swimming pool surrounded by lounge chairs and umbrellas, with a hotel building in the background.

Universal's Endless Summer Resort - Surfside Inn and Suites

International Drive District

10/10 Excellent

Dean

A modern hotel with a curved facade, palm trees, and a clear sky.

Universal's Aventura Hotel

Florida Center

10/10 Excellent

Jade

A spacious lobby with a central seating area, a reception desk, and a visible staircase leading to other floors.

Pestana Orlando Suites - Lake Buena Vista

Orlando

10/10 Excellent

Megan

A modern building with a distinctive facade featuring circular windows and a reflective water feature in front.

Universal's Stella Nova Resort

Orlando

10/10 Excellent

Kristy

A modern hotel room with a large bed, a smaller bed, a desk, and a vanity. There is a window with a view of the night sky.

Universal's Terra Luna Resort

Orlando

10/10 Excellent

kylie

A display of packaged food items on a table with a sign reading "Good all round".

avid hotel Orlando International Airport by IHG

Orlando

10/10 Excellent

David

Find out more about Winter Park

Everything you need to know about Winter Park holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Winter Park holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, cabins, villas... The list goes on, and on… and on!

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Winter Park holiday rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Winter Park holiday rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Winter Park. If you’re looking for a little peace, consider booking during the quieter months, such as . For more hustle and bustle, you may prefer to visit in .

Prices vary throughout the year and depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Winter Park holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Winter Park holiday rentals we have selected for you start as low as NZ$137 per night. Entering your travel dates in the search wizard you might find even better deals!

How to find incredible deals on Winter Park rentals

At Expedia, we put the best Winter Park holiday rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia.

To find some top Winter Park rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Winter Park holiday.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Winter Park. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.

Frequently Asked Questions

Can I find holiday rentals in Winter Park?

Yes, there are holiday rentals in Winter Park close to Kraft Azalea Gardens, or you can select a more secluded option if you're looking for a relaxing stay. Visitors like the top-notch restaurants and shops in Winter Park. Make sure you have time to check out the university setting and gardens during your trip.

What are some of the best holiday rentals that Winter Park has to offer?

Beautiful 9-bedroom house with AC in serene Kissimmee , Bring the whole Family !: This holiday home rental outside of Winter Park has air conditioning and laundry facilities to help you feel perfectly comfortable in your new surroundings.

How many holiday rentals are there in Winter Park?

Expedia has 55 holiday rentals for your stay in Winter Park.

What can I see and do in Winter Park?

Cultural attractions include Casa Feliz Historic Home Museum and Albin Polasek Museum and Sculpture Gardens, whereas Lake Mizell and Kraft Azalea Gardens are a couple of picturesque spots to enjoy the outdoors. Universal Studios Florida and Universal Orlando Resort are other popular places to visit in the area.

What are holiday rentals like in Winter Park?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in Winter Park. Holiday rentals offer amenities such as kitchens and laundry facilities so you'll have a home away from home. If you're concerned about a sanitised environment, holiday rentals can provide a sense of privacy away from public hotel lifts and busy lobbies while still allowing you a great travel experience. You'll also get more space in a holiday rental than in a traditional hotel, which is another reason why a holiday rental is a popular choice for families.

Winter Park Holiday Rentals

Change your mind

Treat yourself

Be picky

Check prices for these dates

Our top choices for Winter Park holiday rentals

1. Quiet and safe neighborhood come to this great place with lots of room for relax

2. Funky Remodeled Otown Bungalow Sleeps 8

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

4. Comfy Tiny Home @WP. Large Private Deck+Queen bed

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

6. 1-bedroom vacation room just 12 minutes from University of Central Florida

7. OASIS UNDER THE OAK TREE.

8. 3-bedroom house in quaint Winter Park with cool vibes

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

10. Spacious 5-bedroom house in gorgeous Winter Park

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

12. Spacious 5-bedroom house in welcoming Winter Park

13. Top 1% Modern Japandi Retreat - Jacuzzi No Fee

14. Luxury Designer Home • Disney, Universal & Downtown

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

16. Suites by The Wellborn

17. The Point Hotel & Suites Orlando

18. Marriott's Grande Vista

19. Stylish & Cozy King Bed Retreat @ Baldwin Park

20. ⛲️Walk to Lake Eola & restaurants

Find holiday rentals that suit your style

Top Winter Park Hotel Reviews

Drury Plaza Hotel Orlando - Disney Springs Area

10/10 Excellent

Find out more about Winter Park

Winter Park holiday rentals: An excellent choice for every season

How to find incredible deals on Winter Park rentals

Frequently Asked Questions

Can I find holiday rentals in Winter Park?

What are some of the best holiday rentals that Winter Park has to offer?

How many holiday rentals are there in Winter Park?

What can I see and do in Winter Park?

What are holiday rentals like in Winter Park?