Winter Park Vacation Rentals from $85: Search Short-Term Rentals

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Our top choices for Winter Park vacation rentals

A modern kitchen with white cabinets, stainless steel appliances, and a black dining chair.

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

Orlando

Olubankole S.

$244 nightly

Nov 16 - Nov 17

Total with taxes and fees

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

2. Funky Remodeled Otown Bungalow Sleeps 8

Fairview Shores

Julia K.

$225 nightly

Dec 3 - Dec 4

Total with taxes and fees

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

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

Fairview Shores

tyson s.

$251 nightly

Nov 30 - Dec 1

Total with taxes and fees

A modern bathroom with a wooden door, a white sink, and a mirror.

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

Fairview Shores

$158 nightly

Nov 23 - Nov 24

Total with taxes and fees

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

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

Fairview Shores

Vicki V.

$224 nightly

Nov 18 - Nov 19

Total with taxes and fees

A swimming pool with a curved edge, surrounded by a concrete deck and a brick border.

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

Orlando

jamie l.

$155 nightly

Nov 16 - Nov 17

Total with taxes and fees

A wooden gate with a metal latch, a clear plastic barrier, and a bicycle parked nearby.

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.

$120 nightly

Dec 6 - Dec 7

Total with taxes and fees

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

$356 nightly

Dec 7 - Dec 8

Total with taxes and fees

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.

$275 nightly

Nov 17 - Nov 18

Total with taxes and fees

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.

$271 nightly

Nov 16 - Nov 17

Total with taxes and fees

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

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

Goldenrod

Ashley C.

$363 nightly

Nov 16 - Nov 17

Total with taxes and fees

12. Spacious 5-bedroom house in welcoming Winter Park

Winter Park

$280 nightly

Nov 16 - Nov 17

Total with taxes and fees

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.

$508 nightly

Nov 22 - Nov 23

Total with taxes and fees

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

14. Luxury Designer Home • Disney, Universal & Downtown

College Park

Christian H.

$560 nightly

Nov 16 - Nov 17

Total with taxes and fees

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.

$271 nightly

Nov 30 - Dec 1

Total with taxes and fees

A sign with 'The Wellborn' written on it, surrounded by lush greenery and a building in the background.

16. Suites by The Wellborn

Lake Cherokee

Wade

$68 nightly

Nov 29 - Nov 30

Total with taxes and fees

A swimming pool with lounge chairs and palm trees.

17. The Point Hotel & Suites Orlando

Florida Center

Lawana

$80 nightly

Dec 15 - Dec 16

Total with taxes and fees

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

18. Marriott's Grande Vista

Orlando

Christina

$96 nightly

Dec 10 - Dec 11

Total with taxes and fees

A modern kitchen with wooden cabinets, a black countertop, a stainless steel refrigerator, a microwave, and a coffee maker.

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.

$166 nightly

Nov 24 - Nov 25

Total with taxes and fees

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Top Winter Park Hotel Reviews

Holiday Inn Resort Orlando Suites - Waterpark by IHG

10/10 Excellent

"Un Exelente servicio volvería sin pensarlo"

Sheraton Vistana Resort Villas, Lake Buena Vista/Orlando

8/10 Good

"The value for the stay for our Disney trip was excellent. We really loved everything about the room and the facilities. The room was huge and amazing for the price. Had plenty of amenities. Having two separate rooms for the kids and a full size living space was clutch with all the stuff we had for four days at Disney parks. Saved us a ton having a full kitchen too. Our only two gripes: 1) the food/price at Azzula was meh. We didn’t order anything special but the tab for two adults and two kids was exceptinally expensive after tax and gratuity. I ordered the adult portion of the chicken tenders and fries. It was literally two small tenders and fries. For the price, it left something to be desired. 2) My wife texted for full housekeeping every day because that’s now apparently the standard at many hotels that you have to request it. The last day we stayed we didn’t get any housekeeping. We contacted the text number and were told it was a light housekeeping service that was towels and trash only (that wasn’t what we asked for). Neither of those things happened. We texted photos of the trash and towels and were told a manager would follow up in the morning. That also never happened. All in all it was an incredible stay and we loved the value. I would avoid eating on property, wasn’t worth the cost. For the most part guest services was responsive but they dropped the ball at multiple points on the one cleaning issue and follow up. Not a make or break for all the other benefits"

Universal's Endless Summer Resort - Dockside Inn and Suites

10/10 Excellent

"Stayed for 3 nights in the 2 bedroom suite, which was spacious, clean, and had everything we needed. The early park admission and the shuttle buses to the parks were a bonus. We enjoyed dinners at the Pier 8 Market which was delicious with many different options. Would definitely stay here again!"

Country Inn & Suites by Radisson, Orlando Airport, FL

8/10 Good

"Hotel was very clean, rooms were nice and bathrooms spotless. Only downfall would be that hotel advertises 3 restaurants at hotel, room service, hot tub/pool. The hotel itself had zero restaurants, and hot tub was sealed off. Staff was excellent and very helpful especially with it being so busy with cruise patrons.."

Find out more about Winter Park

Everything you need to know about Winter Park vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Winter Park vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. 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 vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Winter Park vacation 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 low season months. For more hustle and bustle, you may prefer to visit Winter Park in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $85 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

How to find incredible deals on Winter Park rentals

At Expedia, we put the best Winter Park vacation 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 vacation.

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.

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Things to do in Orlando

Frequently asked questions

Can I find vacation rentals in Winter Park?

Yes, we offer vacation rentals in Winter Park close to Kraft Azalea Gardens, or you can choose 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's the top vacation rental that Winter Park has to offer?

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

How many vacation rentals are there in Winter Park?

Expedia has 55 vacation 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 vacation rentals like in Winter Park?

Vacation rentals are privately owned accommodations you can stay in for several days or more in Winter Park. Vacation rentals offer extras such as patios, hot tubs, and fire pits to help you enjoy your stay. If you're concerned about cleanliness, vacation rentals can provide a sense of safety away from public hotel elevators and lobbies packed with people while still allowing you to travel. You'll also find more space in a vacation rental than in a standard hotel, which is another reason why a vacation rental is a great option for a small group gathering.

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Check prices for these dates

Our top choices for Winter Park vacation 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 vacation rentals that suit your style

Top Winter Park Hotel Reviews

Holiday Inn Resort Orlando Suites - Waterpark by IHG

Find out more about Winter Park

Explore a world of travel with Expedia

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