Winter Park vacation rentals

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Top-rated vacation rentals in Winter Park

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Guest favorite

Apartment in Winter Park

4.95 out of 5 average rating, 282 reviews

Get a Little Glam in a Retro Palm Beach-Style Boudoir

The whole upstairs portion of the building is all yours. Location is prime as it is close to all things wonderful in Winter Park FL. Two streets behind is Lake Killarney. The space is beautifully decorated and offers guests a charming get away. Please note: It is a 13.6 mile drive (21 - 40 minutes depending on traffic) from Universal Studio's and a 21.7mile drive (24 - 45 minutes depending on traffic) to Disney World. There is a lock box located under the stairwell on the left side of the building. I will message you with your code for access. Once you get your key, head on up the stairs and enjoy your home away from home. Welcome! I live 3 minutes away from the Air BnB property and I work in the downstairs portion of the building, so I am local and available to assist with any additional requests. Message me anytime! Or text 407 575 3502 The Fairbanks corridor of Winter Park is the main artery to affluent areas, offering great shopping and dining close by. This hidden gem is a short walk to grocery stores, restaurants, and Winter Park Village shopping district with its movie theater. Light sleepers, please be aware that there is the potential for traffic noise. The BnB offers a large parking lot. You should have no problem at all if you desire to arrive by car. The area is also safe to bike around and Uber or Lyft operates in the area. No smoking please.

Feb 20 – 27

G$23,897 GYD per night

Guest favorite

Bungalow in Winter Park

4.98 out of 5 average rating, 231 reviews

Cozy 2/2 Bungalow - Downtown Winterpark/Orlando

Your family will be close to everything when you stay at this centrally-located bungalow. Located right off I-4, you will be 5 minutes from Downtown Orlando and Downtown Edgewater, 10 min from Downtown Winter Park, 15 min from Universal Studios, and 25 min from Disney! College Park local parks and golf course within walking distance! Large 70 inch 4K tv with surround sound, large sofa to enjoy watching your favorite movies, 2 rooms with queen beds, and 2 bathrooms equipped with bluetooth music

Jul 27 – Aug 3

G$29,190 GYD per night

Guest favorite

Guest suite in Orlando

4.98 out of 5 average rating, 300 reviews

A SUITE RETREAT with a Garden View in the City

A lovely remodeled in-law suite in a 1920s Mission Styled home in College Park suited for 2 people with a separate entrance, private bath & a little kitchenette.The Suite looks out into a garden to offer a relaxing view. Even though you are in the Downtown area, the suite was designed to offer solitude. We are walking distance to many restaurants & only an easy 5 minute drive to downtown Orlando. I am looking forward to hosting any and all who would like to visit. All are welcome. #STR-1009437

Jan 30 – Feb 6

G$16,679 GYD per night

Guest favorite

Bungalow in Maitland

4.86 out of 5 average rating, 488 reviews

Maitland-Orlando Area, FL. Pool House Bungalow

Large open space adjacent to a beautiful pool, waterfall, and fantastic lake view. 27 miles to Disney World, close to Park Avenue, local hospitals, Universities, and less than an hour to local beaches. Only 18 miles to MCO-Orlando International Airport. Great shopping within 3 miles. Location is secluded with large trees, lakeside, and adjacent to the commuter train track. The train runs by on regular basis. Please note in the pictures the pool creates the ambiance to make your stay complete.

Jun 21 – 28

G$22,527 GYD per night

Guest favorite

Guest suite in Winter Park

4.96 out of 5 average rating, 245 reviews

Atmospheric Studio in the Garden

Enjoy a little piece of Florida's lush paradise. Full studio suite lives elegantly & comfortably for longer-term stays. We've taken such pride in the opportunity to allow old Florida to intersect with compelling modern design and styling. Relax in this fully furnished studio apartment with kitchenette nestled among a verdant garden. Home boasts modern kitchen, comfy memory foam bed, separate shower and bath & spacious living and entertaining areas. Available for stays of one month or longer.

May 1 – 8

G$20,348 GYD per night

Guest favorite

Guesthouse in Orlando

4.91 out of 5 average rating, 144 reviews

8th Green Cottage - A relaxing oasis in the city

The 8th Green Cottage is a relaxing oasis in the heart of Orlando. Located 5 minutes from downtown. Sitting on the historic 1924 Dubsdread golf course. Enjoy the great views, pleasant and quiet neighborhood all with easy access to everything Orlando has to offer. Location is key when traveling and the 8th Green Cottage delivers! Disney, Universal, and Sea World all within a straight shot down I4. Free play Arcade with 3500 games included in spare bedroom Pets are welcome and stay Free.

Sep 18 – 25

G$28,143 GYD per night

Guest favorite

Home in Winter Park

4.93 out of 5 average rating, 107 reviews

Modern, Quiet & Cozy - Entire house /Winter park

Embrace Tranquil Living in Winter Park, Florida. Located in a quiet neighborhood NE of downtown this recently renovated house is modern, clean, and cozy. Short drive to other great attractions in Orlando. Its central location is minutes away from Park Ave, the University of Central Florida, Rollins College, Full Sail University, Downtown Orlando, MCO Airport, Amway Center, Dr. Phillips, Science Center, Orlando City Stadium, and much more! You need to be at least 18 years old to book.

Oct 21 – 28

G$33,166 GYD per night

Guest favorite

Home in Maitland

4.96 out of 5 average rating, 113 reviews

The Butterfly Bungalow near Park Ave

This 1950s bungalow has been lovingly restored to maintain it's Florida charm and offer simple comforts. Located in a family-friendly neighborhood just a few blocks from the Enzian Theater, the bungalow is close to restaurants and shops lining the cobblestone streets of Park Ave, and centrally located to historic areas of both Winter Park and Maitland. Park Ave shopping district - 1.5 miles Whole Foods - 0.8 miles Publix - 0.8 miles SunRail - 1.7 miles Downtown Orlando - 8 miles

Jan 2 – 9

G$27,958 GYD per night

Guest favorite

Tiny home in Orlando

4.98 out of 5 average rating, 634 reviews

The Little Treehouse 2 at Country Club of Orlando

With rustic urban charm, The Little Treehouse "2" is a perfect relaxation spot for your stay in the City Beautiful. This completely renovated 1926 carriage house downstairs unit is a 260 sq. ft. blend of cosmopolitan comfort and enchantment. Located 5 minutes from Downtown, Amway Arena, Camping World Stadium, 15 minutes to Universal Studios, 25 minutes to Disney and an hours drive to Florida's beautiful beaches! *Search "Little Tree House Orlando" in your browser for more info.

Dec 28 – Jan 4

G$26,565 GYD per night

Guest favorite

Cottage in Winter Park

4.95 out of 5 average rating, 341 reviews

Winter Park Pearl 6 min drive to historic Park Ave

This Winter Park cottage was built in 1954 with original hardwood flooring. Take a 5 min drive to and through historical Winter Park to access shops and restaurants on the coveted Park Ave. It is the perfect central location to access beaches, Universities, Orlandos events, and the best restaurants. The house is tucked away into a quiet neighborhood with lots of sleepy old big oaks. If you have any questions I am always available, so please ask. My response time is immediate!

May 14 – 21

G$37,975 GYD per night

Superhost

Apartment in Maitland

4.82 out of 5 average rating, 250 reviews

At Mine | Elegant Double Suite in North Orlando

Experience ultimate comfort at our Maitland, FL hotel, ideally located just north of Downtown Orlando. we're the area's largest hotel. Enjoy the convenience and luxury of plush bedding, modern furnishings, and upscale Grohe showers in your room. Relax by our outdoor pool, keep fit in the 24-hour gym, and access the Genesis Health Club. With over 15,000 square feet of event space, secure parking, and free Wi-Fi, we've got you covered.

Sep 28 – Oct 5

G$14,960 GYD per night

Guest favorite

Home in Winter Park

4.9 out of 5 average rating, 129 reviews

Guest Suite in Winter Park/Orlando

This private guest suite is connected to our home but completely exclusive with a separate entrance, private bathroom and no access to the main house. The layout is like a studio apartment with a bedroom, dining area and kitchenette. Outside there is also a patio area for guests. Full Sail University- 5 min University of Central Florida- 15 min Orlando International Airport- 25 min Universal Studios- 25 min Disney World- 30 min

Jun 15 – 22

G$17,884 GYD per night

Vacation rentals for every style

Get the amount of space that is right for you

Popular amenities for Winter Park vacation rentals

Self check-in

Gym

BBQ grill

Laptop-friendly workspace

Wifi

Stay near Winter Park's top sights

Orlando Science Center289 locals recommend

Winter Park Village68 locals recommend

Harry P. Leu Gardens197 locals recommend

AdventHealth Orlando25 locals recommend

Trader Joe's74 locals recommend

Orlando Museum of Art215 locals recommend

Other great vacation rentals in Winter Park

Guest favorite

Guest suite in Orlando

4.94 out of 5 average rating, 146 reviews

Guesthouse in Mills 50 w backyard walking to bars

May 26 – Jun 2

G$21,979 GYD per night

Guest favorite

Loft in Orlando

4.86 out of 5 average rating, 1096 reviews

Downtown (Ivanhoe Village) Loft Apartment

Feb 7 – 14

G$20,347 GYD per night

Guest favorite

Guest suite in Orlando

4.93 out of 5 average rating, 559 reviews

Charming Comfortable Cottage in College Park

Oct 22 – 29

G$20,470 GYD per night

Guest favorite

Guesthouse in Orlando

4.98 out of 5 average rating, 145 reviews

The Loft in College Park

Aug 21 – 28

G$17,684 GYD per night

Guest favorite

Guesthouse in Maitland

4.98 out of 5 average rating, 114 reviews

Private 1-bd Mid-Century Guesthouse

Dec 10 – 17

G$20,267 GYD per night

Guest favorite

Guesthouse in Orlando

4.83 out of 5 average rating, 196 reviews

Lovely Spacious Guesthouse in Mills 50 District

Mar 4 – 11

G$14,342 GYD per night

Guest favorite

Guesthouse in Orlando

4.95 out of 5 average rating, 130 reviews

Jefferson St. Cottage

Feb 10 – 17

G$19,993 GYD per night

Guest favorite

Home in Orlando

4.9 out of 5 average rating, 177 reviews

Cozy Milk District Home | Downtown | Free Parking

Aug 17 – 24

G$19,599 GYD per night

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Other great vacation rentals in Winter Park

Superhost

Guesthouse in Winter Park

4.92 out of 5 average rating, 266 reviews

Tiny Cottage - 3 MI to Downtwn w/ Grill & Hammocks

Oct 19 – 26

G$29,433 GYD per night

Guest favorite

Guest suite in Orlando

4.97 out of 5 average rating, 241 reviews

Unique Place! East End Market! Baldwin/Winter Park

Jun 2 – 9

G$26,898 GYD per night

Guest favorite

Guesthouse in Orlando

5.0 out of 5 average rating, 152 reviews

The Sacred Space Downtown Orlando Milk District

Oct 4 – 11

G$22,779 GYD per night

Guest favorite

Guesthouse in Orlando

4.96 out of 5 average rating, 486 reviews

Private Luxurious Apt. - Historic Downtown Orlando

Jun 24 – Jul 1

G$24,534 GYD per night

Superhost

Condo in Winter Park

4.81 out of 5 average rating, 57 reviews

Lovely Winter Park Home close to Hospitals !

Jan 14 – 21

G$22,170 GYD per night

Guest favorite

Guesthouse in Orlando

4.95 out of 5 average rating, 38 reviews

New Mid Century-Modern Studio

Jul 8 – 15

G$17,531 GYD per night

Guest favorite

Bungalow in Orlando

5.0 out of 5 average rating, 23 reviews

Cozy Cottage in College Park.

Aug 4 – 11

G$16,969 GYD per night

Guest favorite

Apartment in Winter Park

4.88 out of 5 average rating, 32 reviews

The Lake House

Feb 28 – Mar 7

G$19,558 GYD per night

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Quick stats about vacation rentals in Winter Park

Total rentals
410 properties
Rentals with dedicated workspaces
240 properties have a dedicated workspace
Rentals with a pool
110 properties have a pool
Pet-friendly rentals
140 properties allow pets
Family-friendly rentals
200 properties are a good fit for families
Total number of reviews
18K reviews

Frequently Asked Questions

Where should I stay in Winter Park?
Make yourself at home in Winter Park by choosing from our most frequently booked neighborhoods. We have over 1,500 vacation rentals in North Orange, over 1,050 vacation rentals in Lake Formosa, and over 1,990 vacation rentals in Baldwin Park.
Are there vacation rentals with a dedicated workspace in Winter Park?
Yes! Work meets play with ease at over 240 vacation rentals in Winter Park featuring dedicated workspaces. Stay connected and productive in your home away from home.
Are there pet-friendly vacation rentals in Winter Park?
Four-legged friends are welcome in Winter Park. Choose from more than 140 vacation rentals for guests traveling with pets.
Are there Winter Park vacation rentals on Airbnb with pools?
Yes! Dive into the perfect getaway at one of over 110 vacation homes with pools in Winter Park, available on Airbnb. Make a splash and soak up the sun in style!
How much does it cost to stay in bungalow rentals in Winter Park?
Experience the best of Winter Park with our bungalow rentals, starting at about $40 per day, before taxes and fees. Embrace comfort and style while staying within your budget in your home away from home.
Are there family-friendly vacation rentals in Winter Park?
Winter Park has more than 200 family-friendly stays. Amenities on the property may include high chairs, travel cribs, or strollers.
Do apartment rentals in Winter Park have a gym?
Absolutely! We offer over 20 apartment rentals with a gym in Winter Park. Enjoy a tailored experience with all the comforts you desire.
Do house rentals in Winter Park have a bbq area?
Absolutely! We offer over 40 house rentals with a bbq area in Winter Park. Enjoy a tailored experience with all the comforts you desire.
Do condo rentals in Winter Park have self check-in?
Absolutely! We offer over 10 condo rentals with self check-in in Winter Park. Enjoy a tailored experience with all the comforts you desire.
Do apartment rentals in Winter Park have wifi?
Absolutely! We offer over 80 apartment rentals with wifi in Winter Park. Enjoy a tailored experience with all the comforts you desire.

Winter Park vacation rentals

Top-rated vacation rentals in Winter Park

Vacation rentals for every style

Apartments

Houses

Hotels

Popular amenities for Winter Park vacation rentals

Stay near Winter Park's top sights

Other great vacation rentals in Winter Park

Guest suite in Orlando

Loft in Orlando

Guest suite in Orlando

Guesthouse in Orlando

Guesthouse in Maitland

Guesthouse in Orlando

Guesthouse in Orlando

Home in Orlando

Other great vacation rentals in Winter Park

Guesthouse in Winter Park

Guest suite in Orlando

Guesthouse in Orlando

Guesthouse in Orlando

Condo in Winter Park

Guesthouse in Orlando

Bungalow in Orlando

Apartment in Winter Park

Quick stats about vacation rentals in Winter Park

Total rentals

Rentals with dedicated workspaces

Rentals with a pool

Pet-friendly rentals

Family-friendly rentals

Total number of reviews

Frequently Asked Questions

Where should I stay in Winter Park?

Are there vacation rentals with a dedicated workspace in Winter Park?

Are there pet-friendly vacation rentals in Winter Park?

Are there Winter Park vacation rentals on Airbnb with pools?

How much does it cost to stay in bungalow rentals in Winter Park?

Are there family-friendly vacation rentals in Winter Park?

Do apartment rentals in Winter Park have a gym?

Do house rentals in Winter Park have a bbq area?

Do condo rentals in Winter Park have self check-in?

Do apartment rentals in Winter Park have wifi?

Destinations to explore