Vacation rentals in Winter Park

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Top-rated vacation rentals in Winter Park

Guests agree: these stays are highly rated for location, cleanliness, and more.

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Top guest favorite
A spacious living area features a large, deep-seated sectional couch adorned with decorative pillows. A wooden tray rests on the couch. A dining table with chairs is positioned near bright windows, enhancing the natural lighting in the room.
Home in Winter Park
4.97 out of 5 average rating, 159 reviews

Stylish newly updated home in Winter Park

Sleeps 8 people comfortably but can fit 10. This home has VERY CONVENIENT ACCESS TO I-4 making it easy to get to Orlando's most sought after attractions, including Park Avenue, Downtown Orlando, Rollins College, Leu Gardens, Mills Ave, Baldwin Park, College Park, Camping World Stadium, Amway Arena, SunRail, and many hospitals. SHORT WALK to 3 notable restaurants Also nearby: Universal Studios (20 min) Outlet Mall (20 min) International Drive (25 min) Orlando Airport (30 min) Disney (~30-40 min)

Guest favorite
A spacious pool house is visible behind a lush, green lawn, surrounded by trees. A paved path leads to the inviting pool area, while a gated fence provides added privacy. Sunlight filters through the leaves, creating dappled patterns on the grass.
Bungalow in Maitland
4.88 out of 5 average rating, 588 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.

Top guest favorite
The exterior of the Cozy Cottage is designed with a welcoming green facade, featuring glass doors that open to a charming patio. A stone path leads to a small round table with chairs, complemented by a decorative fountain and lush greenery surrounding the area.
Bungalow in College Park
4.98 out of 5 average rating, 121 reviews

Cozy Cottage in College Park.

Whether you're coming to Orlando for adventure at one of the theme parks, or a little R&R, the Cozy Cottage is the perfect place. It's charming, quiet and nestled in our back garden with a stock tank pool in College Park, in The city of Orlando. Winter Park, Rollins college, lou gardens, Orlando Science Center, Advent Heath, Orlando health, Dr. Phillips center, Ivanhoe, lake eola, camping world stadium and the Kia center, are all in the immediate area. UCF, Full Sail and Florida Central too.

Top guest favorite
The light-filled living room features a stylish gray sofa, wooden side tables, and a coffee table. Natural light enters through the large window, illuminated by soft curtains. Decorative plants enhance the inviting ambiance, complemented by warm wooden flooring.
Home in Orlando
4.92 out of 5 average rating, 119 reviews

Charming 2BR Cottage, Downtown Orlando

Bright, cozy 1940’s cottage located in a quiet, safe, family-friendly Downtown Orlando neighborhood. 2 bedroom, 1 bath, onsite parking, full kitchen, washer and dryer, fenced-in back yard and patio area, working desk space in bedroom. Walking distance to the local gems and eateries of Audubon Park and the Mills 50 District! Central location minutes away from Winter Park and Downtown local attractions. 20-30 minutes from Universal, Disney and MCO. Great for a work trip or an Orlando getaway!

Guest favorite
A modern living space is highlighted by a plush grey sofa and mid-century styled furniture. A large window invites natural light, showcasing views of the outdoors. Decorative elements, including a small plant and artwork, add character to the room while maintaining a clean aesthetic.
Loft in Colonialtown South
4.92 out of 5 average rating, 621 reviews

Contemporary Loft Near Downtown

Conveniently located between the foodie-friendly Milk District and Downtown Orlando, this impeccably thought-out space features a spacious loft style open floor plan perfect for a couple or small group. The floor to ceiling windows allow natural light to fill the space while providing complete privacy during your stay. Upscale Winter Park restaurants and the vibrant Thornton Park art scene are only a short drive away. Universal is only 20 minutes away, Disney is 35 minutes, MCO 20 minutes.

Superhost
A cozy bedroom features a comfortable queen bed with light blue bedding. Nightstands with lamps are positioned on either side. A wooden barn door and an artwork depicting foliage add a touch of warmth to the modern space, complemented by a sleek black floor.
Tiny home in Winter Park
4.83 out of 5 average rating, 109 reviews

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

This memorable place is anything but ordinary. Welcome to our charming TINY house in the heart of Orlando! Nestled in a quiet neighborhood, this cozy retreat offers the perfect blend of comfort, privacy, and convenience. Whether you're here for business or leisure, our centrally located TINY house is an ideal home base for exploring all that Orlando and Winter Park have to offer. ✅️Private Patio ✅️Free Parking ✅️Deck with outdoor seating 🎢10-15 min from Universal ✈️20-22 min to airport

Top guest favorite
The bedroom features a spacious bed dressed in soft blue bedding, complemented by two bedside lamps on wooden tables. Decorative curtains with a water-themed design frame the window, while a subtle area rug adds texture to the room's original terrazzo flooring.
Apartment in Winter Park
4.9 out of 5 average rating, 177 reviews

The Lake House

Welcome to the mid-century Lake House. 370 square feet apartment with a private entrance and original terrazzo floors. Located on a quiet residential street on a small lake, and located within a 5-minute drive to anything you may need! Starbucks and Panera are within walking distance, and dozens of other places to eat. Publix, Walgreens, and Sprouts are just around the corner. A short 10 minute drive to the famous Park Ave, in Downtown Winter Park with shopping and gourmet restaurants.

Guest favorite
A comfortable living area features a large sectional sofa, complemented by cushions in various patterns. A stylish geometric wall decor piece is visible, along with a sleek television mounted on the wall, emitting soft ambient lighting. Wood flooring adds warmth to the space.
Bungalow in College Park
4.97 out of 5 average rating, 337 reviews

Cozy 2/2 Home - Downtown Winterpark/Orlando

You will be close to everything when you stay at this centrally-located bungalow. Located right off I-4, 5 minutes from Advent Health Hospital, you will be 5 minutes from Downtown Orlando an, 10 min from Downtown Winter Park, 15 min from Universal Studios, and 25 min from Disney! Dubsdread 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

Top guest favorite
A white door with a glass panel leads into the studio, framed by a decorative welcome mat on stone pavers. Lush green plants are positioned beside the door, adding a natural touch to the entrance. Soft shadows from nearby foliage create a calming atmosphere.
Guest suite in College Park
4.97 out of 5 average rating, 232 reviews

New Mid Century-Modern Studio

Enjoy your stay in this beautifully decorated studio with all the conveniences of home. The bed is Queen. We are located in College Park of Orlando. On Edgewater Drive there are restaurants, bars, and boutique shops. Close to downtown , 30 min. from all the attractions, and 5 min. from one of the city’s largest hospitals, 23 miles from ORMC airport. Walking distance from the historic Dubsdread Golf Club and restaurant. Pet fee required. Please make sure to add the pet to the reservation.

Top guest favorite
Guesthouse in Orlando
4.99 out of 5 average rating, 140 reviews

Baldwin Park Guest House

Welcome to Beautiful Baldwin Park, This  Brand New Private sanctuary with modern day decorations, amenities and large screen television is  the perfect place for a couple or single to experience the beautiful Orlando area. Conveniently located near the Orlando International Airport, Winter Park and downtown area Enjoy your morning coffee on the private patio . This entire property is very clean and well maintained, we look forward to being your host for your next central Florida visit 

Guest favorite
A modern kitchen is seen, featuring white cabinetry and a speckled granite countertop. Stainless steel appliances, including a microwave and toaster, are positioned conveniently. A small potted plant adds a touch of greenery, while natural light filters in through the window above the sink.
Condo in Winter Park
4.83 out of 5 average rating, 107 reviews

Lovely Winter Park Home close to Hospitals !

Lovely Condo close to Full Sail, Rollins College, Valencia College, UCF and Advent Health Winter Park Hospital. Close to Park Avenue - Winter Park’s shopping, dining and cultural gem – boasts more than 140 boutiques, sidewalk cafes, and museums, all in the shadow of oak-canopied Central Park. In addition to the shops, dining and cultural offerings, you can plan a trip around special events that include seasonal art shows, concerts and fashion events.

Guest favorite
A cozy bedroom features a black platform bed dressed in a navy and white patterned duvet. A wooden dresser stands adjacent to the bed, and a small desk is positioned nearby. Natural light illuminates the space, highlighting the serene beach artwork on the wall.
Guest suite in Eatonville
4.97 out of 5 average rating, 191 reviews

Private entrance/bathroom 10 min from DT Orlando

Welcome to your home away from home! Our cozy room with a attached bathroom is the perfect retreat for your visit to Orlando. Located just 10min from downtown Orlando, 30min from MCO and Disney, and 20 min from Universal, you'll have the best of both worlds - convenience and comfort. Whether you're here for business or pleasure, our room is the perfect place to call your temporary home. Book your stay with us today and experience the best of our city.

Popular amenities for Winter Park vacation rentals

When is the best time to visit Winter Park?

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Avg. priceG$24,258 GYDG$24,258 GYDG$24,467 GYDG$23,840 GYDG$23,003 GYDG$23,003 GYDG$22,794 GYDG$22,585 GYDG$21,539 GYDG$23,003 GYDG$24,049 GYDG$24,049 GYD
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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 1,090 vacation rentals in Lake Formosa, over 2,050 vacation rentals in Baldwin Park, and over 460 vacation rentals in Eatonville.

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

    Yes! Work meets play with ease at over 220 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 120 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 townhouse rentals in Winter Park?

    Experience the best of Winter Park with our townhouse rentals, starting at about $30 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 190 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 30 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 townhouse rentals in Winter Park have wifi?

    Absolutely! We offer over 10 townhouse rentals with wifi in Winter Park. Enjoy a tailored experience with all the comforts you desire.

Quick stats about vacation rentals in Winter Park

  • Total vacation rentals

    Explore 380 vacation rentals in Winter Park

  • Verified guest reviews

    Over 18,490 verified reviews to help you choose

  • Family-friendly vacation rentals

    180 properties offer extra space & kid-friendly amenities

  • Pet-friendly vacation rentals

    Find 120 rentals that welcome pets

  • Vacation rentals with a pool

    110 properties feature pools

  • Rentals with dedicated workspaces

    220 properties have a dedicated workspace

  • Wi-Fi availability

    370 of Winter Park vacation rentals include wi-fi access

  • Popular amenities for guests

    Guests love Self check-in, Gym, and BBQ grill across Winter Park rentals

  • 4.8 Average rating

    Winter Park stays are highly rated by guests—averaging 4.8 out of 5!

  • Nearby attractions

    Winter Park's top spots, include Orlando Science Center, Harry P. Leu Gardens, and Orlando Museum of Art

Destinations to explore

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  5. Winter Park