This one-bedroom flat is located in Orlando's Thornton Park district, a short walk from Lake Eola and approximately 1.8 kilometres from Church Street Station and 1.7 kilometres from the Kia Centre. This air-conditioned accommodation offers free WiFi and private parking, with a kitchen equipped with a fridge and microwave oven, and can host up to three guests.
9.8 16 reviews
Winter Park, FL
28/06 – 18/07
82 €/nighttotal: 1640 € (20 )
Yania's Cozy Getaway
1 1
apartment , Azalea Park
This Azalea Park self-contained flat is conveniently located minutes from Waterford Lakes Town Centre and major highways, offering easy access to Orlando's theme parks. The one-bedroom, one-bathroom apartment sleeps two guests and features a private patio, kitchenette with fridge and microwave, air conditioning, internet access, parking, and allows pets; nearby activities include fishing and exploring the area's attractions such as Florida Mall and Orlando International Premium Outlets.
9.9 196 reviews
Winter Park, FL
28/07 – 01/08
96 €/nighttotal: 384 € (4 )
Private 1-bd Mid-century Guesthouse
1 2
house , Altamonte Springs
This Altamonte Springs guesthouse, situated 1.6km from the SunRail station and close to Altamonte Springs' museums and parks, offers convenient access to major highways. The self-contained property features a mid-century modern design, a full kitchen, one bedroom, one bathroom, and can accommodate up to three guests, with a spacious yard and outdoor patio.
9.6 19 reviews
Winter Park, FL
28/07 – 01/08
90 €/nighttotal: 360 € (4 )
Tiny Unit In Cottage In The Middle Of Downtown
1 2
apartment , Orlando
This downtown Orlando flat boasts an exceptional location near Lake Eola, with Publix supermarket directly opposite and is approximately 32-48 km from Universal Studios and 48 km from Walt Disney World. The self-contained studio apartment, measuring approximately 9 sq m, features a private entrance, en-suite bathroom, mini-fridge, coffee maker, Netflix and Amazon Prime, plus a terrace; it sleeps two guests and includes free parking for one car.
10 2 reviews
Winter Park, FL
28/06 – 18/07
93 €/nighttotal: 1860 € (20 )
Cute & Quaint Private Guesthouse With 1 Bed/1 Bath
1 1
house , Winter Park
This guesthouse is situated in a central Winter Park location, just minutes from Advent Health and the dining and shopping on Park Avenue, with easy access to the I-4 for broader Orlando exploration. This one-bedroom guesthouse for two guests offers a fully equipped kitchen, a comfortable living area with a large television, a king-sized bed, and a shared courtyard, all within a quiet neighbourhood setting.
10 2 reviews
Winter Park, FL
28/07 – 01/08
54 €/nighttotal: 216 € (4 )
Hogar Sobre Ruedas
1 2
apartment , Rio Pinar
This self-catering apartment in Orlando's Rio Pinar neighbourhood is conveniently located approximately 15-21 kilometres from attractions such as Church Street Station, the Kia Center, Camping World Stadium, and the Holy Land Experience. The one-bedroom, one-bathroom flat sleeps three guests and features a private terrace with garden views, free Wi-Fi, private parking, air conditioning, and a fully equipped kitchen.
Winter Park, FL
28/06 – 18/07
56 €/nighttotal: 1120 € (20 )
Chic Studio Near Downtown & Theme Parks
1 1
studio , Orlando
This Orlando apartment is situated approximately 8.5 kilometres from Church Street Station and 8.7 kilometres from the Kia Centre, offering convenient access to downtown landmarks. This 37 square metre studio apartment accommodates up to three guests and features a kitchenette with a microwave, complimentary WiFi, air conditioning, and a garden area, with Orlando International Airport located just 10.9 kilometres away.
8.7 6 reviews
Winter Park, FL
28/06 – 18/07
71 €/nighttotal: 1420 € (20 )
Botanical Tranquility
1 1
apartment , Casselberry
This Casselberry apartment is conveniently located approximately 17-24 km from various Orlando attractions including Orlando Sanford International Airport, Addition Financial Arena, and the Florida Mall. The self-catering flat offers one bedroom, one bathroom, sleeps three guests, and boasts a private pool, free Wi-Fi, and parking; nearby activities include visiting the Amway Center and Camping World Stadium.
9.7 191 reviews
Winter Park, FL
28/07 – 01/08
101 €/nighttotal: 404 € (4 )
Cozy Guest House Close To Downtown Orlando
1 2
house , Fairview Shores
This Winter Park guest house offers a prime location, a short 9.6km drive from Rollins College and under 16km from both Orlando and Winter Park city centres. The self-catering property sleeps up to four guests in one bedroom with one bathroom, featuring a queen bed and a queen sleeper sofa, plus a kitchen equipped with a fridge and microwave, air conditioning, parking and excellent guest reviews.
9.7 79 reviews
Winter Park, FL
10/07 – 18/07
148 €/nighttotal: 1184 € (8 )
Cozy Downtown Living Sleeps 8 W/ Free Parking
1 4
apartment , Orlando
This two-bedroom house is situated in downtown Orlando, within walking distance of Lake Eola Park. The property, sleeping up to eight guests, boasts a fully equipped kitchen with quartz countertops, stainless steel appliances, and a bonus room with a pull-out sofa bed and workstation; two free parking spaces are also provided.
10 4 reviews
Winter Park, FL
28/06 – 18/07
91 €/nighttotal: 1820 € (20 )
Private Guest Suite Near Disney & Orlando
1 1
apartment , Altamonte Springs
This Altamonte Springs flat is conveniently located 1.4 km from Sanlando Park, within 4.8 km of Cranes Roost Park, and under 4.8 km from Altamonte Mall. The one-bedroom, one-bathroom apartment sleeps four guests and offers air conditioning, Wi-Fi, and proximity to the Trophy Club of Orlando, making it ideal for exploring Central Florida.
9.9 75 reviews
Winter Park, FL
10/07 – 18/07
211 €/nighttotal: 1688 € (8 )
Charming Bungalow In Winter Park
3 4
apartment , Orlando
This Orwin Manor bungalow offers three bedrooms and two bathrooms, comfortably sleeping six guests, and is conveniently located near Orlando's hospitals and downtown, providing easy access to local restaurants. The 160 square metre single-family home boasts an open-plan layout, hardwood floors, a fully equipped kitchen including a dishwasher, air conditioning, ample parking, and a landscaped yard; emotional support animals are permitted for an additional fee.
Best family friendly Winter Park, FL holiday rentals
Among the 288 accommodations in Winter Park, FL, here are the 4 best family friendly rentals
9.6 117 reviews
Winter Park, FL
28/06 – 18/07
87 €/nighttotal: 1740 € (20 )
Renovated ✓Nature ✓Cozy ✓Walk To Mall Park Publix
1 1
studio , Altamonte Springs
This renovated studio apartment in Altamonte Springs is located within 500 metres of the Altamonte Springs Mall, a park, and a Publix supermarket, offering convenient access to local amenities and a peaceful retreat close to Orlando's attractions. This pet-friendly self-contained unit accommodates up to three guests with flexible sleeping arrangements, featuring a kitchen with a fridge, freezer, microwave, and dishwasher, air conditioning, a garden, fitness centre, and ample parking.
10 109 reviews
Winter Park, FL
28/06 – 18/07
152 €/nighttotal: 3040 € (20 )
Stylish Boutique Guest House In Winter Park
3 1
apartment , Winter Park
This two-bedroom flat is ideally located in Winter Park, just a short distance from attractions like the Casa Feliz Historic Home Museum and the Morse Museum of American Art. It has received excellent reviews from previous guests. The apartment comfortably sleeps four guests and features a fully equipped kitchen, a fireplace, and a balcony. Guests can enjoy the on-site fitness centre, swimming pool, and garden, as well as free Wi-Fi and parking.
9.6 19 reviews
Winter Park, FL
28/06 – 18/07
1295 €/nighttotal: 25900 € (20 )
Renovated Luxury 6000 Sqft Mansion In Downtown Orlando Sleep 14 Near Theme Parks
6 1
apartment , Orlando
This six-bedroom Orlando holiday home is centrally located, within a 2.4km walk of Lake Eola and the Dr Phillips Center for the Performing Arts, and under 5km from Camping World Stadium and the Kia Forum. The 557 square metre property boasts a private water park, on-site arcade, and sleeps up to 14 guests, offering a fully equipped kitchen, swimming pool, spa, and a relaxing garden with a living plant wall.
8.0 1 review
Winter Park, FL
10/07 – 18/07
164 €/nighttotal: 1312 € (8 )
177 M² House ∙ 4 Bedrooms ∙ 8 Guests
4 4
house , Orlando
This spacious four-bedroom house is situated in the Ventura gated community in southeast Orlando, Florida, approximately 9.6km north of Orlando International Airport, offering easy access to attractions such as the Orlando State Diving School and Leroy Hoequist Park. The 177 square metre property sleeps eight guests, boasting a fully equipped kitchen, private swimming pool, games room with table tennis, and high-speed internet; making it ideal for family holidays in Orlando.
Best Winter Park, FL holiday rentals with parking
8.0 2 reviews
Winter Park, FL
28/07 – 01/08
133 €/nighttotal: 532 € (4 )
Cozy Apt W/ Pool, Hot Tub, Golf, Near Downtown!
2 2
apartment , Orlando
This Ventura apartment in Orlando is conveniently located near major theme parks, approximately 13km from Downtown Orlando and 43km from Walt Disney World Resort. This two-bedroom, two-bathroom property sleeps four (with a fifth guest possible for an extra fee), offering a fully equipped kitchen, free Wi-Fi, in-unit laundry, a balcony, and access to a community pool, hot tub, tennis court, and golf course; free parking is available within the gated community.
9.4 10 reviews
Winter Park, FL
28/06 – 18/07
82 €/nighttotal: 1640 € (20 )
Traveler's Dream: Refresh & Recharge Poolside
1 1
apartment , Casselberry
This Casselberry flat is conveniently located approximately 3.5 km from Secret Lake Park and 4.5 km from Red Bug Lake Park, offering easy access to outdoor recreation. The one-bedroom, one-bathroom apartment sleeps two guests and features a private pool, free Wi-Fi, a fully equipped kitchen with fridge and microwave, a smart TV, and access to a community pool; Winter Park Village and Altamonte Mall are within a 10 km radius.
10 13 reviews
Winter Park, FL
28/06 – 18/07
237 €/nighttotal: 4740 € (20 )
Amazing Walkability, Thornton Park Suburb Of Downtown Orlando Walk To Everything
2 1
apartment , Orlando
This two-bedroom, two-bathroom apartment is situated in Orlando's Lake Lawsona Historic District of Thornton Park, within walking distance of Lake Eola Park and a short drive (approx. 24km) from Orlando International Airport (MCO). The 130 square metre property offers a modern interior with two queen-sized beds, a 75-inch smart TV, full kitchen, in-unit laundry, and free private parking; accommodating up to five guests and close to the Dr Phillips Center for the Performing Arts.
9.6 307 reviews
Winter Park, FL
28/06 – 18/07
128 €/nighttotal: 2560 € (20 )
Cute Guest House In Winter Park Minutes From Downtown In Car
1 1
apartment , Fairview Shores
This charming studio apartment is situated just a short drive from the Park Ave strip and Winter Park Village, offering easy access to shopping, dining, and entertainment. Guests consistently rate the property excellent for its location, cleanliness, and overall experience. The studio is compact and comfortable, measuring 30 square metres and accommodating up to two guests. It includes modern amenities such as a kitchenette, refrigerator, air conditioning, smart TV, Wi-Fi internet, a queen-size bed, and a private bathroom with complimentary toiletries.
Frequently asked questions about holiday rentals in Winter Park, FL
What are the top family-friendly attractions in Winter Park, FL?
Families love the Central Park, with its playground and splash pad, and the Albin Polasek Museum & Sculpture Gardens, which has a great kids' area. The Charles Hosmer Morse Museum of American Art also has some engaging exhibits for families.
What are the best Airbnb and holiday rentals in Winter Park, FL?
When is the best time to book a vacation rental in Winter Park, FL?
The best time to book a vacation rental in Winter Park is usually during the shoulder seasons, from September to November and March to May, to avoid the peak crowds and high prices of the winter holidays and summer months.
What are the most popular Airbnbs in Winter Park, FL?
What are the best budget-friendly activities in Winter Park, FL?
For a budget-friendly day out, you can explore the Winter Park Chain of Lakes by renting a kayak or canoe. The Kraft Azalea Garden is another great option, offering beautiful scenery and a peaceful atmosphere.
What are the best holiday rentals with a pool in Winter Park, FL?
What are the best restaurants with local dishes in Winter Park, FL?
For a taste of local cuisine, try The Wine Room, which serves up delicious dishes made with fresh, seasonal ingredients. The Dixie Dharma Kitchen offers a unique blend of Southern and Asian flavours.
What are the best rentals for families and kids in Winter Park, FL?
What are the best walking or cycling routes in Winter Park, FL?
The Winter Park Scenic Loop is a popular walking and cycling route, taking you past the Winter Park Chain of Lakes and through charming residential areas. The West Orange Trail is another great option for cyclists, offering a longer, more scenic ride.
What are the best rentals or Airbnbs with a jacuzzi in Winter Park, FL?
Are there pet-friendly attractions in Winter Park, FL?
Yes, many attractions in Winter Park are pet-friendly. The Kraft Azalea Garden welcomes well-behaved dogs on leash. The Winter Park Chain of Lakes is also a great spot for a walk with your furry friend.
What are the benefits of choosing a vacation rental in Winter Park, FL?
Vacation rentals offer more space and privacy compared to hotels. You can often find rentals with unique features like a private pool or a garden, and they can be a more affordable option for families or groups.
What are the top sports attractions and facilities in Winter Park, FL?
Winter Park is home to the Winter Park Racquet Club, a popular destination for tennis enthusiasts. The Winter Park Golf Course is another great option for golfers, offering a challenging and scenic experience.
Destinations nearby
Best Winter Park, FL holiday rentals with a balcony
10 6 reviews
Winter Park, FL
10/07 – 18/07
438 €/nighttotal: 3504 € (8 )
Brand New Luxury Modern 5br/4.5ba+game Room Home
5 4
apartment , Altamonte Springs
This Altamonte Springs flat is situated 39 kilometres from the Magic Kingdom and 29 kilometres from Universal Studios Florida, offering convenient access to major Orlando theme parks. This spacious 307 square metre residence features five bedrooms, four bathrooms, and accommodates up to 15 guests with amenities including a fully equipped kitchen, a dedicated game room, and ample parking.
Winter Park, FL
28/07 – 01/08
147 €/nighttotal: 588 € (4 )
Upstay 2br Golfer's Retreat W Patio Ventura Resort
2 2
apartment , Orlando
This two-bedroom flat is located in the secure, gated Ventura community in East Orlando, 16 kilometres from Orlando International Airport and 40 kilometres from Walt Disney World Resort. This 85 square metre condo accommodates up to four guests and features a fully equipped kitchen, a private furnished patio with golf course views, and complimentary access to the community clubhouse with a swimming pool and fitness centre.
9.9 9 reviews
Winter Park, FL
10/07 – 18/07
272 €/nighttotal: 2176 € (8 )
2 Bdrm Penthouse With Billiards
1 4
apartment , Orlando
This Orlando penthouse apartment is situated in the city centre, less than 0.6km from various attractions and 14km from Orlando International Airport. The 150 square metre dwelling boasts two bedrooms, two bathrooms, a fully equipped kitchen, in-unit laundry, a billiards table, free Wi-Fi, and accommodates up to seven guests.
Winter Park, FL
28/07 – 01/08
130 €/nighttotal: 520 € (4 )
Cozy Apt With Pool, Hot Tub, Golf, Near Downtown
2 2
house , Orlando
This Orlando dwelling is situated 8.05 kilometres from Church Street Station and 8.19 kilometres from the Kia Centre, with Orlando International Airport a mere 8.05 kilometres away. This 76 square metre holiday home accommodates up to seven guests and features a kitchen with a fridge, microwave, and dishwasher, air conditioning, a swimming pool, hot tub, balcony, garden, fitness centre, and tennis courts, with free Wi-Fi provided.
Best pet friendly Winter Park, FL holiday rentals
Among the 288 accommodations in Winter Park, FL, here are the 4 best pet friendly rentals
9.6 119 reviews
Winter Park, FL
28/06 – 18/07
81 €/nighttotal: 1620 € (20 )
1bd Apt In Downtown W/ King Bed |Office, Free Prkg
1 1
apartment , Orlando
This downtown Orlando flat is situated three blocks from the city's busiest streets, within walking distance of Lake Eola Park and a short drive (approximately 32km) from Walt Disney World Resort and Universal Orlando Resort. The self-catering apartment offers a king-size bed, dedicated workspace, fully equipped kitchen, on-site laundry, private parking, and accommodates two guests, with keyless access and excellent guest reviews.
10 2 reviews
Winter Park, FL
28/06 – 18/07
331 €/nighttotal: 6620 € (20 )
Game Day Getaway-downtown Orlando
4 1
apartment , Orlando
This Orlando flat is located in the West Lake District, 1.1 kilometres from Camping World Stadium and 1.2 kilometres from Tinker Field. This 4-bedroom, 2-bathroom flat sleeps 13 guests and offers a fully equipped kitchen with microwave and dishwasher, air conditioning, internet access, and on-site laundry facilities, with proximity to Orlando International Premium Outlets, Mall at Millenia, Universal Orlando Resort, and The Orlando Eye.
Winter Park, FL
28/06 – 18/07
209 €/nighttotal: 4180 € (20 )
Lovely Space In Downtown Orlando
2 1
apartment , Orlando
This **Orlando apartment** is located in Downtown Orlando, a 13-minute walk from Church Street Station and within 644 metres of the city centre. This spacious **Orlando flat** offers 2 bedrooms, 2 bathrooms, accommodates up to 7 guests, and features a fully equipped kitchen, complimentary WiFi, air conditioning, and a private balcony, with a fitness centre available on-site.
10 17 reviews
Winter Park, FL
28/06 – 18/07
421 €/nighttotal: 8420 € (20 )
Recharge @ Timberland Lodge: Pool Hottub Sauna
4 1
apartment , Wekiwa Springs
This charming chalet is located in Longwood, Florida, just a short drive from Wekiwa Springs State Park and other local attractions. It’s rated excellent by previous guests and offers a peaceful retreat in a tranquil setting. The chalet has four bedrooms and three bathrooms, comfortably accommodating up to eleven guests. It also features a private pool, sauna, and outdoor shower, alongside a fully equipped kitchen, air conditioning, and a jacuzzi for ultimate relaxation.
