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.

Jul 5 – 12

ﺩ.ﺇ432 per night

Guest favorite

Home in Winter Park

4.9 out of 5 average rating, 132 reviews

Guest Suite in Winter Park/Orlando

This private guest suite is next 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- 1 mile University of Central Florida- 7 miles Orlando Int'l Airport - 11 miles Universal Studios- 18 miles Disney World- 23.8 miles Camping World Stadium- 10 miles Kia Center- 9 miles Downtown-8 miles

Jun 20 – 27

ﺩ.ﺇ305 per night

Guest favorite

Bungalow in Winter Park

4.98 out of 5 average rating, 232 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

Aug 5 – 12

ﺩ.ﺇ513 per night

Guest favorite

Guest suite in Orlando

4.98 out of 5 average rating, 301 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

Oct 13 – 20

ﺩ.ﺇ293 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.

May 25 – Jun 1

ﺩ.ﺇ352 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.

Jun 15 – 22

ﺩ.ﺇ372 per night

Guest favorite

Guesthouse in Orlando

4.97 out of 5 average rating, 286 reviews

Oasis Garden Cottage -cozy, chic, near everything!

Our cozy cottage is located within minutes of some of the best areas, restaurants, bars, and attractions Orlando has to offer. Winter Park and College Park are 3-5 minute drives, Disney and Universal only 20 minutes, etc. The interior is chic and inviting, with a homey feel. Enjoy the fireplace, play some board games, soak in bath salts in the claw foot tub, curl up on the porch with a coffee and read one of our provided books— it’s so peaceful you’ll have a hard time leaving for the day!

Oct 1 – 8

ﺩ.ﺇ398 per night

Guest favorite

Home in Maitland

4.97 out of 5 average rating, 115 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

Jul 30 – Aug 6

ﺩ.ﺇ491 per night

Guest favorite

Tiny home in Orlando

4.98 out of 5 average rating, 636 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.

Aug 6 – 13

ﺩ.ﺇ467 per night

Guest favorite

Guesthouse in Winter Park

4.98 out of 5 average rating, 249 reviews

Private and Peaceful with Full Kitchen

Welcome to our spacious, secure getaway tucked in a quiet Winter Park neighborhood. Enjoy full kitchen, hardwood floors, high ceilings, superfast WiFi and lots of TV steaming options, walk-in closets and walk-in shower. The hosts live in a separate space attached to the house. Your suite and patio are completely private. Please register all guests when making your reservation. For everyone’s safety, we ask that there be no visitors besides registered guests.

May 20 – 27

ﺩ.ﺇ362 per night

Guest favorite

Guesthouse in Orlando

4.98 out of 5 average rating, 145 reviews

The Loft in College Park

The Loft is a private guesthouse located above our garage near Downtown Orlando and Ivanhoe Village. It is walking distance to multiple restaurants, bars and shops. Also close to I-4 and easy access to the attractions. The studio space offers a queen size bed as well as a queen size sleeper sofa in the living room area. Luxurious full size bathroom with walk in shower and rain shower head. Perfect get away for those looking to enjoy Orlando!

Sep 22 – 29

ﺩ.ﺇ324 per night

Guest favorite

Guesthouse in Orlando

4.95 out of 5 average rating, 131 reviews

Jefferson St. Cottage

This cottage is a unique free-standing detached dwelling in the heart of Lawsona Park (Historic Downtown Orlando). It sits behind the owner's main house in the back of the lot. The cottage is newly updated with all the amenities to give guests a perfect secluded area near bars, eateries, parks as well as easy access to highways to visit Universal, Disney World, Sea World any more attractions in central Florida.

Apr 20 – 27

ﺩ.ﺇ355 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

Guesthouse in Orlando

4.91 out of 5 average rating, 144 reviews

8th Green Cottage - A relaxing oasis in the city

Jun 27 – Jul 4

ﺩ.ﺇ479 per night

Guest favorite

Guest suite in Orlando

4.93 out of 5 average rating, 147 reviews

Guesthouse in Mills 50 w backyard walking to bars

Dec 4 – 11

ﺩ.ﺇ429 per night

Guest favorite

Guesthouse in Orlando

4.96 out of 5 average rating, 488 reviews

Private Luxurious Apt. - Historic Downtown Orlando

Jul 7 – 14

ﺩ.ﺇ431 per night

Guest favorite

Guest suite in Orlando

4.93 out of 5 average rating, 560 reviews

Charming Comfortable Cottage in College Park

Jan 31 – Feb 7

ﺩ.ﺇ357 per night

Guest favorite

Yurt in Orlando

4.96 out of 5 average rating, 219 reviews

Lakefront Sunset Yurt King Bed *A/C* Kayaks, Bikes

May 27 – Jun 1

ﺩ.ﺇ443 per night

Guest favorite

Guesthouse in Orlando

4.93 out of 5 average rating, 160 reviews

Private Backyard Cottage in Mills50

Aug 13 – 20

ﺩ.ﺇ349 per night

Guest favorite

Guesthouse in Orlando

4.89 out of 5 average rating, 607 reviews

Thornton Park's Historic Guest House - private

Aug 18 – 25

ﺩ.ﺇ287 per night

Guest favorite

Tiny home in Orlando

4.93 out of 5 average rating, 111 reviews

Luxury Tiny Home -2 MI to DT Orlando & Winter Park

Aug 4 – 11

ﺩ.ﺇ375 per night

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Other great vacation rentals in Winter Park

Guest favorite

Loft in Orlando

4.87 out of 5 average rating, 1098 reviews

Downtown (Ivanhoe Village) Loft Apartment

Aug 23 – 30

ﺩ.ﺇ358 per night

Guest favorite

Home in Winter Park

4.94 out of 5 average rating, 108 reviews

Modern, Quiet & Cozy - Entire house /Winter park

Jun 17 – 24

ﺩ.ﺇ550 per night

Guest favorite

Guesthouse in Orlando

5.0 out of 5 average rating, 152 reviews

The Sacred Space Downtown Orlando Milk District

Aug 21 – 28

ﺩ.ﺇ403 per night

Guest favorite

Guest suite in Orlando

4.97 out of 5 average rating, 243 reviews

Unique Place! East End Market! Baldwin/Winter Park

Jun 14 – 21

ﺩ.ﺇ473 per night

Guest favorite

Home in Orlando

4.9 out of 5 average rating, 177 reviews

Downtown Orlando-Harwood House-Lake Eola-Historic

Apr 16 – 23

ﺩ.ﺇ413 per night

Guest favorite

Guesthouse in Orlando

4.95 out of 5 average rating, 40 reviews

New Mid Century-Modern Studio

Jul 8 – 15

ﺩ.ﺇ308 per night

Superhost

Condo in Winter Park

4.81 out of 5 average rating, 58 reviews

Lovely Winter Park Home close to Hospitals !

Dec 9 – 16

ﺩ.ﺇ390 per night

Guest favorite

Tiny home in Winter Park

4.89 out of 5 average rating, 19 reviews

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

May 16 – 23

ﺩ.ﺇ403 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 condo rentals in Winter Park?
Experience the best of Winter Park with our condo 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 house rentals in Winter Park have a gym?
Absolutely! We offer over 10 house rentals with a gym in Winter Park. Enjoy a tailored experience with all the comforts you desire.
Do apartment rentals in Winter Park have a bbq area?
Absolutely! We offer over 20 apartment 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 condo rentals in Winter Park have wifi?
Absolutely! We offer over 10 condo 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

Guesthouse in Orlando

Guest suite in Orlando

Guesthouse in Orlando

Guest suite in Orlando

Yurt in Orlando

Guesthouse in Orlando

Guesthouse in Orlando

Tiny home in Orlando

Other great vacation rentals in Winter Park

Loft in Orlando

Home in Winter Park

Guesthouse in Orlando

Guest suite in Orlando

Home in Orlando

Guesthouse in Orlando

Condo in Winter Park

Tiny home 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 condo rentals in Winter Park?

Are there family-friendly vacation rentals in Winter Park?

Do house rentals in Winter Park have a gym?

Do apartment rentals in Winter Park have a bbq area?

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

Do condo rentals in Winter Park have wifi?

Destinations to explore