Winter Park Vacation Rentals from SAR 243: Search Short-Term Rentals

A clock with 'Winter Park' and 'Central Park' inscribed, surrounded by lush greenery and trees.

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Our top choices for Winter Park vacation rentals

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

Orlando

Olubankole S.

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

2. Funky Remodeled Otown Bungalow Sleeps 8

Fairview Shores

Julia K.

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.

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

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.

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.

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.

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

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.

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.

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.

12. Spacious 5-bedroom house in welcoming Winter Park

Winter Park

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.

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.

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.

A bed with white bedding, a teal headboard, and a bedside lamp on a white nightstand.

16. Suites by The Wellborn

Lake Cherokee

Wade

SAR 285 total

includes taxes & fees

29 Nov - 30 Nov

A swimming pool with lounge chairs and palm trees.

17. The Point Hotel & Suites Orlando

Florida Center

Susan

SAR 320 total

includes taxes & fees

29 Nov - 30 Nov

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

18. Marriott's Grande Vista

Orlando

Christina

SAR 405 total

includes taxes & fees

2 Dec - 3 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.

SAR 775 total

includes taxes & fees

8 Dec - 9 Dec

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Find vacation rentals that suit your style

Top Winter Park Hotel Reviews

A multi-story hotel with balconies, a swimming pool, and a landscaped courtyard.

The Alfond Inn

Winter Park

10/10 Excellent

Gail

An outdoor seating area with a fire feature, cushioned benches, and chairs.

SpringHill Suites by Marriott Winter Park

Winter Park

10/10 Excellent

Michelle

A modern interior with a reception desk, a food display, and a beverage cooler.

Hilton Garden Inn Winter Park

Winter Park

10/10 Excellent

yvon

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

Amy Dawn

A stone wall, a brown sofa with orange and yellow cushions, a glass table with a fire feature, and a wooden door with decorative glass panels.

The Delaney Hotel

South Orange

10/10 Excellent

Chelsea

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

Rosen Shingle Creek

Orlando

10/10 Excellent

Narciso

A cozy living room with a leather sofa, a wooden coffee table, and a leather armchair. There are potted plants and a staircase in the background.

Park Plaza Hotel

Park Avenue District

10/10 Excellent

Deborah

A spacious lobby with a reception desk, seating area with sofas and armchairs, and large windows allowing natural light.

Comfort Suites Downtown

Ivanhoe Village

10/10 Excellent

Glenn

A hotel reception area with two reception desks, a fire extinguisher, a vending machine, and a wall-mounted information board.

Holiday Inn Express Orlando – South Park by IHG

Orlando

10/10 Excellent

Magdalena

A hotel with a modern design, featuring a prominent entrance and a parking area.

Staybridge Suites Orlando Universal Blvd by IHG

Orlando

10/10 Excellent

It's very rare that I take the time to write reviews, but I would be remiss not to review this hotel! This hotel is very high on the list of best places I've stayed anywhere, domestically and abroad. We had the most wonderful time here! the property is immaculate and clean. The breakfast was such a nice surprise. It's not just a little counter with a few pastries and coffee like some other places. It is a full breakfast with so many options (omelets, sausage, waffles, juices. yogurt bar, etc.)...

Sondra

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

Chris

A multi-story hotel with a prominent red sign, a well-lit entrance, and a landscaped front yard.

Hampton Inn & Suites Orlando Airport @ Gateway Village

Airport North

10/10 Excellent

Christine

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

jordan

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

The beginning of a great stay started with Carmen at the front desk. We felt welcomed, informed and appreciated. I read reviews about the hot water, but we had no problem; the shower was great with adequate hot water. The rooms were clean and cleaned daily. The mattresses isn’t plush but I slept well. The shuttle to City Walk and Universal Studios theme parks and early entry into parks was a plus. The restaurant and Starbucks on property were convenient. The property is in a great location and...

Tanya

A modern hotel with a flat facade, large windows, and a parking lot.

EVEN Hotel Orlando International Airport by IHG

Airport North

10/10 Excellent

Kelli

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

This hotel was just minutes away from the airport and provided a convenient shuttle to and from the terminal. The property was modern, spotless, and offered a great breakfast with plenty of quick options. Alex at the front desk was incredibly kind, helpful, and an absolute pleasure to interact with. Jose, the shuttle driver, went above and beyond by sharing helpful tips about the area and dining options. I would definitely stay here again! Additionally, their sister hotel, located just a few...

Lesen

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

Christopher

A covered outdoor seating area with wooden tables and chairs, a pool in the background, and a ceiling fan.

Universal's Endless Summer Resort - Dockside Inn and Suites

Florida Center

10/10 Excellent

cynthia

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

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.

Winter Park Vacation Rentals

Change your mind

Treat yourself

Be picky

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

The Alfond Inn

10/10 Excellent

Frequently Asked Questions

Can I find vacation rentals in Winter Park?

What's the top vacation rental that Winter Park has to offer?

How many vacation rentals are there in Winter Park?

What can I see and do in Winter Park?

What are vacation rentals like in Winter Park?