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Holiday houses in Winter Park

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Top-rated holiday rentals in Winter Park

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

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Guest favourite
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
4.87 out of 5 average rating, 599 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.

Guest favourite
A cozy bedroom showcases a queen bed with an orange floral duvet cover and matching pillows. Three pieces of wall art in soft hues are displayed above the headboard. A door leading to the private entrance is visible, providing easy access.
Apartment in College Park
4.93 out of 5 average rating, 297 reviews

College Park/Winter Pk 1 bed/bath private entrance

255 sq ft studio- queen bed, workspace, kitchenette, large bathroom, private yard area & entrance. This gem is clean & quiet w/ complete blackout in bedroom. Bathroom has tons of natural light & 3 shower heads. There’s TV w/Roku, microwave, fridge & Keurig. Comfy, peaceful at I-4 Par exit # 44. $20 pet fee No cleaning fee. Universal 11 mi Kia Center 3 mi Airports (MCO) (SFB) 23 mi Orlando City Soccer 4.6 AdventHealth Orlando 0.6 mi Orlando Health, Arnold/Winnie Palmer 3.8 Rollins College 1.9

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
4.81 out of 5 average rating, 121 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

Guest favourite
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, 197 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 favourite
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, 344 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 favourite
A stylish kitchen is equipped with modern stainless steel appliances, including a refrigerator and microwave. A central island features two metallic stools, and the cabinetry is finished in a soft gray. A small potted plant adds a touch of greenery to the space.
Guesthouse in Orwin Manor
4.99 out of 5 average rating, 105 reviews

Location, Location, Location!

Enjoy a stylish experience at this centrally-located Guest House. It is located in an excellent area close to the downtown Orlando, excellent restaurants, and much more. It is fully furnished and equipped with new appliances (washer and dryer included) and furniture. It is located minutes from Winter Park, Downtown Orlando and theme parks. Downtown Orlando 3 miles (6 min) Advent Health Hospital 0.6 miles (2 min) Walt Disney World 20 miles (23 min) Universal Studios 11 miles (18 min)

Top Guest favourite
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, 267 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.

Guest favourite
A cozy studio suite is shown with warm wood accents. A small kitchenette is equipped with a microwave and refrigerator. A workspace with a blue desk and two chairs is visible. Bright green plants add a touch of nature, complemented by a vibrant area rug.
Guesthouse in Orlando
4.76 out of 5 average rating, 544 reviews

Private Cozy Cottage in heart of Orlando

Come stay at our Cozy quaint suite located in the historic downtown Lake Davis neighborhood with a 5 minute walk to a quiet neighborhood market, 1 mile walk to downtown Orlando with entertainment and the Downtown Farmers Market. Less than 30 minutes to the worlds greatest attractions Disney, Universal Studios, Sea World etc. The beach is a 1 hour drive. One car parking. The room is connected to a family home you’re able to hear guest next door. Not for parties . Please NO pets.

Top Guest favourite
A contemporary living area features a large flat-screen TV mounted on a wall. A wooden console table sits beneath it, displaying decorative items. Two upholstered chairs provide seating, with a colorful area rug added for warmth. Natural light filters through window coverings.
Apartment in Winter Park
4.96 out of 5 average rating, 222 reviews

Apt C -Modern Elegance in the Heart of Winter Park

Light, bright and full of delight! Fastest internet speed available: 154MBPS download and 20 MBPS upload! Great Location! If you haven't explored Winter Park's Park Avenue, then you must! Heated pool , poolside grill and bikes for your enjoyment! Three blocks to Park Ave and two blocks to the Winter Park Village! Simple elegance downtown defined by contemporary design and leisurely living. Enjoy the convenience and tranquility of one of Florida's best walking communities

Top Guest favourite
A cozy living space is shown, featuring a teal sofa and a yellow armchair beside a round coffee table. Two windows with bamboo shades allow natural light to enter, while a small desk and chair are visible in the corner, enhancing the usability of the room.
Guesthouse in Orlando
5 out of 5 average rating, 106 reviews

Detached suite in Mills 50 food paradise

Our cozy urban-jungle retreat puts you in the heart of an impressive food district and is centrally located. You’ll be a short drive/walk from dozens of diverse restaurants and several concert venues. Our detached suite is great for both business travel (5 min from downtown) and pleasure (30 min from the theme parks). The main room of the suite has space for lounging, a wet bar, and a small desk. It connects to a room with a queen bed and ensuite bathroom.

Guest favourite
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
4.84 out of 5 average rating, 113 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 favourite
The exterior of a modern shipping container suite is displayed, featuring large windows that allow natural light to flood the interior. The surrounding landscape includes gravel and low-maintenance foliage, with a small deck leading to the entrance, emphasizing the blend of nature and contemporary design.
Tiny home in College Park
4.95 out of 5 average rating, 170 reviews

Shipping Container Oasis -HotTub- 30 min to Disney

Step into this unique experience: a shipping container transformed into a luxury 1 bedroom 1 bathroom suite. The space is perfect for couples, business travelers, tourists, and families. After a busy day in the parks or shopping, come back to a cozy outdoor paradise with lights strung up under a covered pergola. Lounge on the couch and enjoy a gas fireplace table, grill a meal on the Weber Spirit 2 gas grill, and soak your tired feet in the hot tub.

Popular amenities for Winter Park holiday rentals

KitchenWifiPoolFree parking on premisesAir conditioning

Stay near Winter Park's top sights

Orlando Science Center

435 locals recommend

Full Sail University

31 locals recommend

AdventHealth Orlando

30 locals recommend

Orlando Museum of Art

278 locals recommend

Harry P. Leu Gardens

290 locals recommend

Charles Hosmer Morse Museum of American Art

194 locals recommend

Other great holiday rentals in Winter Park

Guest favourite
Condo in Winter Park
4.94 out of 5 average rating, 35 reviews

Charming 2/1 Condo on a Lake in Winter Park

Guest favourite
Home in Winter Park
4.93 out of 5 average rating, 15 reviews

3BR House minutes walk to Park Ave and golf course

Guest favourite
The kitchen features white cabinetry and a large island with two cushioned stools. Stainless steel appliances, including a refrigerator and oven, are included. Natural light is provided by multiple windows, enhancing the bright and functional space.
Home in Winter Park
4.87 out of 5 average rating, 75 reviews

Stylish Bungalow

Top Guest favourite
A modern pool house is featured, with large glass doors opening to a swimming pool. The exterior includes a tree emblem and a small seating area with a chair. Sun loungers are positioned near the pool, surrounded by lush grass and a wooden fence.
Guesthouse in College Park
4.98 out of 5 average rating, 99 reviews

Amazing New Pool House!

Superhost
A vibrant welcome sign for Orlando, Florida is depicted, featuring an artistic skyline with tall buildings. A colorful Ferris wheel is visible, along with various recreational activities by the water, including boats and beachgoers. Palm trees frame the scene, enhancing its lively atmosphere.
Apartment in Orlando
4.87 out of 5 average rating, 68 reviews

Luxury Apt + Pool + BBQ + Gym.

Guest favourite
Apartment in Winter Park
4.86 out of 5 average rating, 35 reviews

Small Budget Minded Clean Private Effic. Apartment

Superhost
A modern dining area features a round glass table surrounded by four black chairs with wooden legs. A minimalist floral artwork hangs on the wall, and sunlight filters through vertical blinds, creating a bright and open atmosphere. A soft area rug adds texture to the floor.
Apartment in Winter Park
5 out of 5 average rating, 3 reviews

Kick off your shoes and Unwind

Guest favourite
A cozy bedroom features a spacious bed with a deep green headboard and coordinating bedding. A tufted bench is positioned at the foot of the bed. Natural light enters through a window, illuminating a side table and a small seating area with a fan overhead.
Guesthouse in Orlando
4.92 out of 5 average rating, 38 reviews

Love Nest Studio nearby highways and Airport

When is the best time to visit Winter Park?

MonthJanFebMarAprMayJunJulAugSepOctNovDec
Avg. price$194 NZD$194 NZD$196 NZD$191 NZD$184 NZD$184 NZD$183 NZD$181 NZD$173 NZD$186 NZD$209 NZD$209 NZD
Avg. temp16°C18°C20°C22°C25°C27°C28°C28°C27°C24°C20°C17°C

Frequently Asked Questions

  • What are the best places to stay in Winter Park?

    Many visitors look for stays near Park Avenue for easy access to local shops, dining, and cultural sites. The areas around lakes or in tree-lined neighborhoods also have charming rentals favored for a quieter atmosphere.

  • What are the best things to do in Winter Park with kids?

    Picnic and play in Central Park, join a scenic boat tour, or explore interactive exhibits at nearby museums. Seasonal festivals and farmers markets often have child-friendly activities.

  • What are some of the best things to do in Winter Park?

    Explore the gardens and art collections at The Charles Hosmer Morse Museum of American Art, stroll Park Avenue's boutiques and cafes, and enjoy a scenic boat tour around local lakes. The area has vibrant markets and peaceful green spaces.

  • How is the weather in Winter Park?

    Winter Park has mild winters around 49–72°F (10–22°C) and warm, humid summers between 72–92°F (22–33°C), with wetter conditions in summer and early fall. Lightweight clothing and rain gear are often suggested, especially during the summer months.

  • When is the best time to visit Winter Park?

    Spring and autumn are often recommended, with pleasant temperatures and less rain than summer. Many visitors plan trips around art festivals or holiday celebrations for more activities.

  • What are the best places to visit in Winter Park?

    Visitors frequently explore the Charles Hosmer Morse Museum of American Art, stroll Central Park, and discover shops and eateries on Park Avenue. Scenic lake views and public gardens are also often suggested.

  • What are some hiking trails in Winter Park?

    Winter Park has natural spaces like Mead Botanical Garden, where walking paths wind through gardens and wooded areas. You can also explore community parks with short nature trails and birdwatching opportunities.

  • What are some family activities we can do in Winter Park?

    Families often explore nearby parks, visit hands-on museums, and enjoy scenic boat rides. Picnics around the lakes and browsing local farmers markets can also make for engaging days together.

  • What are some of the best day trip ideas from Winter Park?

    Explore nearby natural springs, botanical gardens, or art museums in surrounding towns. Cultural sites, local food markets, and state parks provide varied options for short getaways.

  • Are there any pet friendly accommodations available in Winter Park?

    Winter Park has pet friendly accommodations, including rentals in residential areas and near walking trails. Some properties may feature private yards or easy access to green spaces for dogs.

  • What are some local tips for visiting Winter Park?

    Reserve indoor activities during warm, wet afternoons in summer, and consider outdoor events in spring or fall for milder weather. Check local calendars for art walks or market days to mingle with residents.

  • What is Winter Park known for?

    Winter Park is known for its tree-lined avenues, public parks, and vibrant arts scene anchored by museums and galleries. Seasonal festivals, lakeside recreation, and locally owned businesses reflect its community-centered spirit.

  • What are the best hidden gems to explore in Winter Park?

    The Albin Polasek Museum & Sculpture Gardens, tucked along a scenic lake, is often mentioned as a unique local spot. Smaller galleries, cozy cafes, and vibrant farmers markets invite exploration off the main avenue.

  • What are the best foods to try in Winter Park?

    Winter Park has locally inspired fare such as fresh Florida seafood, Cuban sandwiches, and handcrafted ice cream. Many recommend tasting dishes from cafés and bakeries along Park Avenue.

  • What should I bring for a trip to Winter Park?

    Pack lightweight clothing, rain gear, and comfortable walking shoes for exploring city parks and museums. Sunscreen, hats, and reusable water bottles are frequently suggested for outdoor activities.

  • What is the nightlife in Winter Park like?

    Winter Park's nightlife includes relaxed bars, jazz lounges, and locally rooted restaurants around Park Avenue. Live music and small venues create an inviting scene for evening outings.

  • What are the most popular events or festivals in Winter Park?

    Winter Park hosts an annual arts festival in spring and has recurring holiday celebrations around the end of the year. Seasonal food and wine events are often recommended for a lively local experience.

  • Are there family friendly vacation rentals in Winter Park?

    Winter Park has many vacation rentals suitable for families, with options in residential neighborhoods and near parks. Features like full kitchens and multiple bedrooms are often available for group stays.

Quick stats about holiday rentals in Winter Park

  • Total holiday rentals

    Explore 380 holiday rentals in Winter Park

  • Verified guest reviews

    Over 19,020 verified reviews to help you choose

  • Family-friendly holiday rentals

    180 properties offer extra space and kid-friendly amenities

  • Pet-friendly accommodation

    Find 120 rentals that welcome pets

  • Holiday 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 holiday 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

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