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, 283 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.

Mar 6 – 13

$98 per night

Guest favorite

Home in Winter Park

4.9 out of 5 average rating, 135 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 28 – Jul 5

$66 per night

Guest favorite

Bungalow in Winter Park

4.98 out of 5 average rating, 234 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 9 – 16

$121 per night

Guest favorite

Guest suite in Orlando

4.98 out of 5 average rating, 303 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

Apr 20 – 27

$69 per night

Guest favorite

Bungalow in Maitland

4.86 out of 5 average rating, 492 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.

Sep 28 – Oct 5

$80 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

$86 per night

Guest favorite

Guesthouse in Orlando

4.91 out of 5 average rating, 145 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 9 – 16

$116 per night

Guest favorite

Home in Maitland

4.97 out of 5 average rating, 117 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

Nov 24 – Dec 1

$115 per night

Guest favorite

Tiny home in Orlando

4.98 out of 5 average rating, 639 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 6 – 13

$103 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.

Jul 20 – 27

$85 per night

Superhost

Apartment in Maitland

4.81 out of 5 average rating, 263 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.

Aug 26 – Sep 2

$56 per night

Guest favorite

Guesthouse in Maitland

4.87 out of 5 average rating, 381 reviews

Chez Bienvenu

Close proximity to Park Avenue in Winter Park! Sunny and Adorable Vintage Guest House ...entire spacious guest house; with private entrance and driveway* Just a couple of blocks off Park Avenue to enjoy Shopping! Cafes! Museums! Nestled in quiet family community* •Smart TV •Stackable washer and dryer included in the unit. •Grill, Beach Chairs, Fishing Poles available •750 square feet of living space

Aug 20 – 27

$84 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

Mead Botanical Garden52 locals recommend

Other great vacation rentals in Winter Park

Guest favorite

Guesthouse in Orlando

4.95 out of 5 average rating, 132 reviews

Jefferson St. Cottage

Nov 22 – 29

$84 per night

Guest favorite

Guesthouse in Orlando

4.97 out of 5 average rating, 287 reviews

Oasis Garden Cottage -cozy, chic, near everything!

Oct 13 – 20

$93 per night

Guest favorite

Guesthouse in Orlando

4.98 out of 5 average rating, 148 reviews

The Loft in College Park

Aug 18 – 25

$75 per night

Guest favorite

Apartment in Orlando

4.95 out of 5 average rating, 619 reviews

Quiet Shed in Downtown

Aug 12 – 19

$86 per night

Guest favorite

Guesthouse in Orlando

4.96 out of 5 average rating, 490 reviews

Private Luxurious Apt. - Historic Downtown Orlando

Jul 15 – 22

$102 per night

Guest favorite

Guesthouse in Orlando

4.93 out of 5 average rating, 160 reviews

Private Backyard Cottage in Mills50

Aug 13 – 20

$83 per night

Guest favorite

Home in Orlando

4.91 out of 5 average rating, 180 reviews

Cozy Milk District Home | Downtown | Free Parking

Aug 17 – 24

$80 per night

Guest favorite

Treehouse in Saint Cloud

4.97 out of 5 average rating, 790 reviews

TreeHouse in the Cloud, (Close toTheme Parks

Jan 21 – 28

$146 per night

Show all

Other great vacation rentals in Winter Park

Guest favorite

Loft in Orlando

4.92 out of 5 average rating, 772 reviews

UPSCALE LOFT SPACE CLOSE TO DOWNTOWN.

Aug 7 – 14

$147 per night

Guest favorite

Guesthouse in Orlando

4.84 out of 5 average rating, 200 reviews

Lovely Spacious Guesthouse in Mills 50 District

Feb 15 – 22

$59 per night

Guest favorite

Guesthouse in Orlando

5.0 out of 5 average rating, 162 reviews

Treehouse Inn Downtown Orlando, 2 bedrooms 2 bath

Jul 2 – 9

$105 per night

Guest favorite

Guest suite in Altamonte Springs

4.96 out of 5 average rating, 384 reviews

Guest Suite! Key West in Altamonte Springs!

Aug 30 – Sep 6

$97 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 15 – 22

$111 per night

Guest favorite

Yurt in Orlando

4.96 out of 5 average rating, 222 reviews

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

May 27 – Jun 1

$105 per night

Guest favorite

Guest suite in Altamonte Springs

4.96 out of 5 average rating, 316 reviews

St. Augustine suite

Nov 18 – 25

$81 per night

Guest favorite

Guest suite in Orlando

4.93 out of 5 average rating, 562 reviews

Charming Comfortable Cottage in College Park

Aug 2 – 9

$102 per night

Show all

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 1,990 vacation rentals in Baldwin Park, over 1,050 vacation rentals in Lake Formosa, and over 1,500 vacation rentals in North Orange.
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.
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.
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.
Are there Winter Park apartment rentals on Airbnb with pools?
Yes! Dive into the perfect getaway at one of over 30 apartment rentals with pools in Winter Park, available on Airbnb. Make a splash and soak up the sun in style!
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 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.
Are there family-friendly apartment rentals in Winter Park?
Winter Park has more than 30 family-friendly apartment rentals. Amenities on the property may include high chairs, travel cribs, or strollers.

Winter Park vacation rentals

Top-rated vacation rentals in Winter Park

Vacation rentals for every style

Houses

Apartments

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

Guesthouse in Orlando

Guesthouse in Orlando

Apartment in Orlando

Guesthouse in Orlando

Guesthouse in Orlando

Home in Orlando

Treehouse in Saint Cloud

Other great vacation rentals in Winter Park

Loft in Orlando

Guesthouse in Orlando

Guesthouse in Orlando

Guest suite in Altamonte Springs

Guest suite in Orlando

Yurt in Orlando

Guest suite in Altamonte Springs

Guest suite in Orlando

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?

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

Do house rentals in Winter Park have a gym?

Are there Winter Park apartment rentals on Airbnb with pools?

Do house 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?

Are there family-friendly apartment rentals in Winter Park?

Destinations to explore