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

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Check prices for these dates

In two weeks
Nov 6 - Nov 8
In two months
Dec 18 - Dec 20
In three months
Jan 15 - Jan 17
In four months
Feb 12 - Feb 14

Our top choices for Winter Park condo rentals

A modern kitchen with grey cabinets, a wooden countertop, and a built-in stove.

1. Lake Eola view 1 bedroom Thornton Park

Lake Eola view 1 bedroom Thornton Park
South Eola
10.0 out of 10, Exceptional, (15 reviews)
"Clean and quiet spot with an easy check-in process. Super close to the lake with lots of restaurants within walking distance. Parking was easy to access and made getting in and out quite easy."
United States
Caroline V.
The price is CA $121
CA $249 total
includes taxes & fees
Oct 26 - Oct 27
Lake Eola view 1 bedroom Thornton Park
A modern kitchen with stainless steel appliances, white cabinetry, and a black countertop.

2. Renovated Condo Lake Eola View Great Location

Renovated Condo Lake Eola View Great Location
South Eola
10.0 out of 10, Exceptional, (18 reviews)
"Great location and home! "
United States
Emma D.
The price is CA $150
CA $283 total
includes taxes & fees
Oct 26 - Oct 27
Renovated Condo Lake Eola View Great Location
A living room with a sectional sofa, two side tables with lamps, a glass coffee table, and a patterned rug.

3. Vintage 2 Bedroom Condo Lake Eola View

Vintage 2 Bedroom Condo Lake Eola View
South Eola
9.8 out of 10, Exceptional, (15 reviews)
"rooms were really nice and clean. parking was smooth n easy. check in was also really smooth"
United States
Daniel
The price is CA $150
CA $303 total
includes taxes & fees
Oct 26 - Oct 27
Vintage 2 Bedroom Condo Lake Eola View
A living room with a sofa, ottoman, coffee table, and a floor lamp.

4. Retro lake Eola 1 Bedroom Condo Thornton park

Retro lake Eola 1 Bedroom Condo Thornton park
South Eola
9.6 out of 10, Exceptional, (8 reviews)
"Perfect location and stay. Communications were great, check in easy and everything was comfortable. Will stay again!"
United States
Genevieve N.
The price is CA $121
CA $249 total
includes taxes & fees
Nov 1 - Nov 2
Retro lake Eola 1 Bedroom Condo Thornton park
A modern kitchen with white appliances, a dining area with a round table and chairs, and a view of the outdoors through a sliding door.

5. Cozy 1-bedroom Condo in Luxury Gated Community

Cozy 1-bedroom Condo in Luxury Gated Community
Ventura
10.0 out of 10, Exceptional, (12 reviews)
"Great place to stay for the price so you can spend money in other areas other than all on your place of stay."
United States
Hassan B.
The price is CA $147
CA $361 total
includes taxes & fees
Oct 29 - Oct 30
Cozy 1-bedroom Condo in Luxury Gated Community
A balcony with wicker furniture, a potted plant, and a view of a water body.

6. Sensational Water View 1 Mile to Disney Newly Renovated Superb Location

Sensational Water View 1 Mile to Disney Newly Renovated Superb Location
Orlando
9.8 out of 10, Exceptional, (230 reviews)
"I have stayed at this condo many times. Clean, comfortable and easy access to Orlando activities."
United States
Jolene O.
The price is CA $84
CA $288 total
includes taxes & fees
Oct 25 - Oct 26
Sensational Water View 1 Mile to Disney Newly Renovated Superb Location
An aerial view of a resort with a large, kidney-shaped pool surrounded by lounge areas and a dock extending into a lake.

7. Top-Floor Lakefront Condo · Disney Fireworks View · Balcony & Resort Pools

Top-Floor Lakefront Condo · Disney Fireworks View · Balcony & Resort Pools
Orlando
9.4 out of 10, Exceptional, (80 reviews)
"Thanks for another great stay!"
United States
Amy S.
The price is CA $154
CA $452 total
includes taxes & fees
Oct 24 - Oct 25
Top-Floor Lakefront Condo · Disney Fireworks View · Balcony & Resort Pools
A swimming pool with lounge chairs and tables, a view of a sunset over a body of water, and a building with balconies.

8. Lakefront Condo · Disney Fireworks, Sunrise Views · Heated Pools · 2 Full Baths

Lakefront Condo · Disney Fireworks, Sunrise Views · Heated Pools · 2 Full Baths
Orlando
9.6 out of 10, Exceptional, (51 reviews)
"Great place to stay and enjoy all the amenities "
United States
Tia S.
The price is CA $140
CA $431 total
includes taxes & fees
Oct 25 - Oct 26
Lakefront Condo · Disney Fireworks, Sunrise Views · Heated Pools · 2 Full Baths
A swimming pool with multiple water features, surrounded by palm trees and hotel buildings.

9. Magical Moment Vacation Condos

Magical Moment Vacation Condos
4.5 star property
International Drive District
6.4 out of 10, (9 reviews)
"Very Clean room staff were great !! Definitely would stay again !"
United States
stephanie
The price is CA $104
CA $442 total
includes taxes & fees
Oct 25 - Oct 26
Magical Moment Vacation Condos
A beachfront dining area with round tables and chairs, surrounded by a natural landscape and a body of water.

10. Free Theme Park Shuttle Transfer, Free Breakfast, Outdoor Pool | Staybridge Near Seaworld

Free Theme Park Shuttle Transfer, Free Breakfast, Outdoor Pool | Staybridge Near Seaworld
Orlando
10.0 out of 10, Exceptional, (3 reviews)
"Very clean and the beds were so comfortable."
United States
Dawn N.
The price is CA $186
CA $237 total
includes taxes & fees
Oct 29 - Oct 30
Free Theme Park Shuttle Transfer, Free Breakfast, Outdoor Pool | Staybridge Near Seaworld
A resort with multiple swimming pools, palm trees, and a parking area.

11. Vc11-405 - 3BR Condo With Resort Access in Orlando

Vc11-405 - 3BR Condo With Resort Access in Orlando
4.0 star property
Orlando
The price is CA $280
CA $588 total
includes taxes & fees
Nov 10 - Nov 11
Vc11-405 - 3BR Condo With Resort Access in Orlando
A swimming pool with multiple water features, surrounded by palm trees and hotel buildings.

12. Animal Kingdoms 2BR Condo only 8 minutes to Disney

Animal Kingdoms 2BR Condo only 8 minutes to Disney
International Drive District
The price is CA $159
CA $561 total
includes taxes & fees
Nov 1 - Nov 2
Animal Kingdoms 2BR Condo only 8 minutes to Disney
A modern kitchen with white cabinets, stainless steel appliances, and a central island with bar stools.

13. DOUBLE FLAT STUDIO - UNIVERSAL STUDIOS & INTERNATIONAL DRIVE

DOUBLE FLAT STUDIO - UNIVERSAL STUDIOS & INTERNATIONAL DRIVE
International Drive District
8.6 out of 10, Excellent, (12 reviews)
"Perfect location for our adventures at all the Universal theme parks. Condo was just right for two couples. "
United States
Charity J.
The price is CA $98
CA $372 total
includes taxes & fees
Oct 27 - Oct 28
DOUBLE FLAT STUDIO - UNIVERSAL STUDIOS & INTERNATIONAL DRIVE
A hotel with a swimming pool, a bridge, and a view of a lake at sunset.

14. Renovated Lakefront Condo · Disney 1 Mile · Fireworks Views · 2 Full Baths

Renovated Lakefront Condo · Disney 1 Mile · Fireworks Views · 2 Full Baths
Orlando
9.4 out of 10, Exceptional, (267 reviews)
"Great stay"
United States
Sarah L.
The price is CA $146
CA $439 total
includes taxes & fees
Oct 26 - Oct 27
Renovated Lakefront Condo · Disney 1 Mile · Fireworks Views · 2 Full Baths
An aerial view of a resort with a central swimming pool, sun loungers, and a separate pool area.

15. 4114-306 Spacious 3bd condo at Vista Cay Resort

4114-306 Spacious 3bd condo at Vista Cay Resort
Orlando
9.6 out of 10, Exceptional, (7 reviews)
"Very nice place!"
United States
Laura S.
The price is CA $116
CA $599 total
includes taxes & fees
Nov 9 - Nov 10
4114-306 Spacious 3bd condo at Vista Cay Resort
A dining area with a glass table, cushioned chairs, and a chandelier.

16. Modern Condo 5min to Conv Center with balcony

Modern Condo 5min to Conv Center with balcony
Orlando
9.0 out of 10, Wonderful, (37 reviews)
"Perfect location and very clean. A great place to stay!"
United States
Frank O.
The price is CA $144
CA $418 total
includes taxes & fees
Oct 24 - Oct 25
Modern Condo 5min to Conv Center with balcony
A pool area with a pergola, lounge chairs, and umbrellas.

17. VCR2-106 - 2BR condo near Disney and universal

VCR2-106 - 2BR condo near Disney and universal
Orlando
10.0 out of 10, Exceptional, (7 reviews)
"Great stay"
United States
McKenzie F.
The price is CA $190
CA $546 total
includes taxes & fees
Oct 31 - Nov 1
VCR2-106 - 2BR condo near Disney and universal
A water park with a water slide, pool, and surrounding buildings.

18. Top Floor VistaCay Near Convention &Universal Epic

Top Floor VistaCay Near Convention &Universal Epic
Orlando
10.0 out of 10, Exceptional, (158 reviews)
"Our stay was great, the whole place was very clean! The unit was well equipped with everything you could need."
United States
Tracy D.
The price is CA $182
CA $567 total
includes taxes & fees
Nov 4 - Nov 5
Top Floor VistaCay Near Convention &Universal Epic
A modern indoor swimming pool with clear glass walls, a hot tub, and lounge chairs.

19. 2 BR RESORT IN PERFECT LOCATION NEAR UNIVERSAL

2 BR RESORT IN PERFECT LOCATION NEAR UNIVERSAL
Florida Center
8.2 out of 10, Very good, (86 reviews)
"Amazing a wonderful vacation"
United States
Tim O.
The price is CA $195
CA $452 total
includes taxes & fees
Oct 31 - Nov 1
2 BR RESORT IN PERFECT LOCATION NEAR UNIVERSAL
A water play area with slides and water jets, surrounded by a paved walkway and palm trees, with buildings in the background.

20. 5000-408 - 3 BED, 2 BATH, POOL AND LAKEVIEW

5000-408 - 3 BED, 2 BATH, POOL AND LAKEVIEW
Orlando
9.6 out of 10, Exceptional, (274 reviews)
"My family and I really enjoyed staying at this property. It was very clean and the owner was very responsive and accommodating. Also, the check in and check out processes were very easy. We really liked how close the property was to the Disney Parks. I would definitely stay at this property again."
United States
Danielle A.
The price is CA $146
CA $575 total
includes taxes & fees
Oct 25 - Oct 26
5000-408 - 3 BED, 2 BATH, POOL AND LAKEVIEW
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Top Winter Park Hotel Reviews

Universal's Cabana Bay Beach Resort

Universal's Cabana Bay Beach Resort

10/10 Excellent
"Todo súper bueno"
ANIURIS 2-night trip
Posted less than an hour ago
Universal's Cabana Bay Beach Resort

Find out more about Winter Park

Winter Park Condo Rentals information

Number of reviews
958
Accommodation
2055 Condo Rentals
Lowest Price
CA $237
Highest Price
CA $599

Frequently asked questions

How much do condos in Winter Park cost?
You'll pay from CA $237 to CA $599 per night for condos in Winter Park. No matter your budget, an ideal stay is a click away on Expedia. These prices were available on Expedia within the past 7 days, for a hotel booking with a check-in date within the next year. Prices reflect current offers and availability is subject to change. Additional terms may apply.
What are the best condos in Winter Park?
A favourite is 55 W #2901. Get comfortable at this 3.5-star stay which offers a swimming pool and fitness facilities. 55 W #3006 is another highly rated condo worth considering. Spend your break at this popular 3.5-star option and make the most of amenities like a swimming pool and a lake view. You'll have your pick of multiple condos in Winter Park with a total average guest review rating of 9.6.
How many condos are there in Winter Park?
Winter Park has 2055 condos. To help you find the perfect stay, use our filters to search for the must-have hotel conveniences.
Are there any family-friendly condos in Winter Park?
Many travellers seeking family-friendly condos in Winter Park book 55 W #2901. With a 3.5-star rating and amenities such as a swimming pool and fitness facilities, you'll feel right at home here. Alternatively, have a look at 3.5-star 55 W #3006. A lake view and a deck help make it a comfy base for your Winter Park trip. Winter Park has tons of family-friendly attractions to visit when the kids are getting restless. Orlando Science Centre and Orlando Museum of Art promise a fun day out for both young and old.
Why book your condo in Winter Park with Expedia?
Reserving a condo in Winter Park is as easy as clicking on your travel dates and selecting an option that has what you need. On the search for something affordable or upmarket, or a stay that also comes with a pool and free WiFi? Use Expedia's search filters to narrow your results even further and find your dream fit.
How can I find cheap condos in Winter Park?
The easiest way to compare cheap condos in Winter Park is with Expedia's easy-to-use filter tool. Refine your search results by amenities, budget and star rating to nab unbeatable bargains in just a few clicks.
What is there to do in Winter Park near my condo?
You'll find loads of terrific things that'll fill up your itinerary in Winter Park. Head for big attractions like Winter Park Country Club, Crealde School of Art and Winter Park Village. Casa Feliz Historic Home Museum, Albin Polasek Museum and Sculpture Gardens and Kraft Azalea Gardens are other highlights.

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