This centrally located apartment in Eatonville is within easy reach of the town's attractions, making it a great base for exploring. It has consistently received excellent ratings for cleanliness, location, and overall experience, ensuring a comfortable stay. The apartment features three bedrooms and two bathrooms, comfortably accommodating up to five guests. It comes equipped with a modern kitchen, a garden, and parking, offering everything you need for a relaxing and enjoyable trip.
Winter Park, FL
14/08 – 21/08
100 €/nighttotal: 700 € (7 )
76 M² Apartment ∙ 2 Bedrooms ∙ 4 Guests
2 2
apartment , Orlando
This two-bedroom condo in Orlando offers a family-friendly base with convenient access to Universal Orlando Resort, SeaWorld Orlando, and Orlando International Airport, located within 19 kilometres of the latter. This 76 square metre apartment accommodates up to four guests and features a full kitchen, a private balcony, and access to resort amenities including a swimming pool, fitness centre, and pickleball courts.
9.9 351 reviews
Winter Park, FL
28/06 – 18/07
117 €/nighttotal: 2340 € (20 )
Cozy 2/2 Home - Downtown Winterpark/orlando
1 1
bungalow , Fairview Shores
This charming bungalow in College Park is ideally situated for exploring Fairview Shores, with easy access to Downtown Orlando, Downtown Edgewater, Downtown Winter Park, Universal Studios, and Disney. The property has consistently received excellent reviews for its location, cleanliness, and overall experience. The two-bedroom, two-bathroom property can comfortably accommodate up to five guests. You'll enjoy modern amenities, a spacious entertainment area with a large TV, comfortable bedrooms, and Bluetooth music in both bathrooms.
9.7 50 reviews
Winter Park, FL
14/08 – 21/08
50 €/nighttotal: 350 € (7 )
Love Nest Studio Nearby Highways And Airport
1 2
house , Azalea Park
This Azalea Park house offers convenient access to Orlando's major roadways (408, 417, I-4), lying approximately 29km from Orlando International Airport, 56km from Walt Disney World Resort, and 40km from Universal Studios Florida and SeaWorld. The single-bathroom property sleeps two guests and includes air conditioning, internet access, and is situated near Full Sail University, the University of Central Florida, and Barry University.
9.9 34 reviews
Winter Park, FL
14/08 – 21/08
103 €/nighttotal: 721 € (7 )
Tropical Oasis / Stylish Orlando Retreat
1 2
house , Orlando
This private guesthouse is situated in Orlando's historic Lake Eola Heights district, just 160 metres from Lake Eola and within walking distance of the Dr. Phillips Centre and Kia Centre. This one-bedroom, one-bathroom apartment accommodates up to four guests and features a well-equipped kitchen, air conditioning, and Wi-Fi, with a modular sofa and queen-size air mattress offering flexible sleeping arrangements, plus access to an outdoor space with games.
9.4 130 reviews
Winter Park, FL
28/07 – 01/08
191 €/nighttotal: 764 € (4 )
Balfour Villa
1 2
house , Winter Park
This two-bedroom house is located in Winter Park, just a short walk from Park Avenue, a bustling street lined with shops and restaurants, and within 5 kilometres of Rollins College. The property boasts a private swimming pool, a well-equipped kitchen, and a spacious living area, ideal for a family or group of friends seeking a relaxing and comfortable stay in the heart of Winter Park.
9.9 61 reviews
Winter Park, FL
10/07 – 18/07
181 €/nighttotal: 1448 € (8 )
10 Min To Winter Park, Games, Gym, King Bd, Coffee
1 4
apartment , Casselberry
This Casselberry apartment, less than 48km from Walt Disney World and Universal Studios and 13km from Winter Park, offers easy access to major Orlando attractions. The three-bedroom, two-bathroom property sleeps nine, boasting a chef's kitchen, dedicated home gym, children's play area with trampoline and slide, and amenities including fast Wi-Fi and a smart TV.
9.5 85 reviews
Winter Park, FL
14/08 – 21/08
106 €/nighttotal: 742 € (7 )
Private City Oasis
1 2
apartment , Azalea Park
This apartment is located in Azalea Park, just under 19 kilometres from downtown Orlando and its bars and restaurants, and within 48 kilometres of major theme parks like Universal Studios, Sea World, ICON Park, and Walt Disney World. It has received excellent ratings for location, cleanliness, and overall user experience. This spacious home offers two bathrooms and can accommodate up to five guests. Amenities include a fully equipped kitchen, a private hot tub, a garden, and parking.
9.9 32 reviews
Winter Park, FL
10/07 – 18/07
157 €/nighttotal: 1256 € (8 )
The Bungalow On Shine
1 4
bungalow , Orlando
This Orlando guesthouse, situated in a desirable neighbourhood a short walk (approx. 1.6km) from Lake Eola and Thornton Park, offers easy access to Universal Studios and Disney World (approx. 48km). The two-bedroom, two-bathroom property sleeps six, features a fully equipped kitchen with modern appliances, complimentary coffee/tea, free high-speed Wi-Fi, YouTube TV, and keyless self check-in; free street parking is available nearby.
8.8 74 reviews
Winter Park, FL
28/07 – 01/08
88 €/nighttotal: 352 € (4 )
Suites By The Wellborn
1 2
apartment , Orlando
Holiday rental listing with an excellent rating of 88% based on 74 reviews. Your accommodation will be located in Orlando. Facilities and services include a kitchen, air conditioning and free parking. This apartment also has a garden!
10 10 reviews
Winter Park, FL
14/08 – 21/08
106 €/nighttotal: 742 € (7 )
Walkable Mills 50 Cottage W/ Patio Under Oak Tree
1 2
house , Orlando
This one-bedroom flat is located in Orlando's Mills 50 district, 3.2 kilometres from downtown Orlando and within walking distance of numerous local eateries, coffee shops, and art venues. This self-catering accommodation sleeps up to four guests and features a fully equipped kitchen, air conditioning, and a garden with a private outdoor space.
9.9 77 reviews
Winter Park, FL
28/07 – 01/08
114 €/nighttotal: 456 € (4 )
Nook Haven | Glamping Retreat •Pool • Hot Tub
1 2
glamping , Goldenrod
This motorhome is located in a quiet Winter Park cul-de-sac, approximately 7 minutes from Park Avenue's dining and shopping, and 20 minutes from Universal Orlando Resort. The "Glamping Rv*free Parking *Private Patio*sleeps 5" offer provides a 140 sq ft temperature-controlled RV with a queen bed, twin bunks, and kitchenette, alongside access to a shared pool, hot tub, grill, and fire pit, all within a private 200 sq ft patio for up to 5 guests.
Best family friendly Winter Park, FL holiday rentals
Among the 288 accommodations in Winter Park, FL, here are the 4 best family friendly rentals
9.9 99 reviews
Winter Park, FL
28/07 – 01/08
109 €/nighttotal: 436 € (4 )
Roy's Guest House
1 2
house , Orlando
Roy's guest house offers a private, quiet retreat in Orlando, Florida, conveniently located 5km from Church Street Station, 6km from the Amway Center, and 7.6km from Camping World Stadium. This self-catering property boasts a 39 square metre floor area with one bedroom, one bathroom, sleeping up to three guests, and features a fully equipped kitchen, free Wi-Fi, and a private garden.
8.8 11 reviews
Winter Park, FL
14/08 – 21/08
67 €/nighttotal: 469 € (7 )
Tiny House In Orlando
1 2
apartment , Maitland
This Lockhart apartment, a self-contained flat ideal for solo travellers, is unfortunately lacking precise location details, preventing specification of proximity to local landmarks. The 1-bedroom, 1-bathroom unit offers air conditioning, Wi-Fi, linens, towels, and basic toiletries; further details regarding size, layout, and nearby attractions are unavailable.
9.5 66 reviews
Winter Park, FL
10/07 – 18/07
230 €/nighttotal: 1840 € (8 )
Spacious Central Florida Home Family Friendly!
4 4
house , Wekiwa Springs
This house is situated in Orlando, 19 kilometres from Camping World Stadium, 21 kilometres from Church Street Station, and 24 kilometres from the Orlando area, offering a peaceful escape from the city's buzz while remaining conveniently close to its attractions. It receives consistently excellent ratings for location, cleanliness, and user experience, ensuring a comfortable and enjoyable stay. The property spans 297 square metres and comfortably accommodates up to eight guests across its four bedrooms. Guests can enjoy a range of amenities, including a fully equipped kitchen, a garden, a spa, a fitness centre, and a Jacuzzi, making it ideal for families or groups looking for a relaxing and well-equipped holiday home.
9.6 25 reviews
Winter Park, FL
10/07 – 18/07
219 €/nighttotal: 1752 € (8 )
Quiet Retreat 15 Minutes From Downtown Orlando, Orlando Airport International!
3 4
apartment , Azalea Park
Golden Cove Rental is situated in Azalea Park, a peaceful residential neighbourhood in Orlando, just 15km from Orlando International Airport, Interstate 4, and the city centre. This apartment has received very good user ratings, making it a popular choice for travellers. This three-bedroom, two-bathroom property can accommodate up to 10 guests, making it ideal for families or groups. The apartment offers a range of amenities, including a fully equipped kitchen, air conditioning, a garden, a tennis court, and parking.
Best Winter Park, FL holiday rentals with parking
Winter Park, FL
28/06 – 18/07
74 €/nighttotal: 1480 € (20 )
Cute & Cozy Guest Suite In Orlando Near Disney, Universal, Downtown, And Airport
1 1
apartment , Conway
This private studio apartment in Conway is situated near the Sodo and Hourglass Districts, offering convenient access to Orlando International Airport (24 km), Disney (40 km), Universal Studios (32 km), and Downtown Orlando (24 km). This soundproofed suite accommodates up to four guests and features air conditioning, internet, and parking, making it an ideal base for exploring nearby attractions such as Universal Orlando Resort and Florida Mall.
9.8 13 reviews
Winter Park, FL
14/08 – 21/08
120 €/nighttotal: 840 € (7 )
Entire Condo At Ventura - Comfy, Quiet Oasis In The Heart Of Orlando
2 2
apartment , Orlando
This two-bedroom apartment is situated in Ventura, a quiet neighbourhood in Orlando, just 10 kilometres from Orlando International Airport and 20 kilometres from the Disney Parks. It has received excellent reviews from previous guests. The apartment is ideal for families or groups of up to six people. It features a fully equipped kitchen, air conditioning, a swimming pool, a terrace, and parking. You can also enjoy on-site amenities such as tennis and pickleball courts, and an 18-hole golf course.
9.0 4 reviews
Winter Park, FL
10/07 – 18/07
166 €/nighttotal: 1328 € (8 )
Spacious Orlando Retreat W/ Backyard Oasis Near Downtown & Attractions
2 4
apartment , Fairview Shores
This two-bedroom flat in Orlando's Fairview Shores district provides a peaceful base, situated just a short drive from Walt Disney World Resort, Universal Studios & Islands of Adventure, and Downtown Orlando's entertainment and healthcare facilities. This accommodation for up to five guests includes a microwave oven, dishwasher, air conditioning, and parking, with a private backyard and the allowance of pets, making it suitable for families and professionals alike.
9.9 122 reviews
Winter Park, FL
28/06 – 18/07
120 €/nighttotal: 2400 € (20 )
The Emerald | Walk To Downtown Orlando & Lake Eola
2 1
apartment , Orlando
This charming apartment is located in Downtown Orlando, just 15 kilometres from Universal Studios and the airport. It has received excellent ratings for cleanliness, location, and user experience. The apartment, which can comfortably accommodate four guests, features a spacious living area and a well-equipped kitchen. It also offers amenities such as a private entrance, on-site parking, and a rainforest shower, making it a perfect choice for those looking for a comfortable and convenient stay in Orlando.
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
Winter Park, FL
14/08 – 21/08
359 €/nighttotal: 2513 € (7 )
349 M² Casa ∙ 8 Quartos ∙ 24 Hóspedes
8 2
house , Orlando
This expansive 8-bedroom villa in Storey Lake, Kissimmee, offers a prime location just 6.4 kilometres from Walt Disney World and minutes from Universal Studios, SeaWorld, and premier golf courses. This property boasts a generous 349 square metre floor area, accommodating up to 24 guests with a private screened pool, spa, and a dedicated games room featuring Foosball, Air Hockey, and an NBA Game Machine.
9.8 38 reviews
Winter Park, FL
10/07 – 18/07
444 €/nighttotal: 3552 € (8 )
*Travel Themed Property With Backyard Oasis*
6 4
apartment , Casselberry
This six-bedroom apartment is located in Maitland, a suburb of Orlando, just 15 kilometres from Casselberry and within walking distance of a Walmart Supercenter and various restaurants. The apartment is rated excellent by previous guests and offers a comfortable and convenient base for exploring the many attractions of Orlando. The apartment spans 232 square metres and comfortably accommodates up to 14 guests. It features a private pool, an outdoor kitchen, a fire pit, a game room, a travel-themed design, and a separate one-bedroom "Castaway Island" apartment.
Winter Park, FL
14/08 – 21/08
145 €/nighttotal: 1015 € (7 )
Modern Getaway Close To Disney
1 2
apartment , Orlando
This Orlando flat offers easy access to Walt Disney World and Universal Orlando Resort, being just a short drive away, and is also conveniently located approximately 3 kilometres from The Mall at Millenia and Florida Mall. This residence accommodates up to eight guests and features a fully equipped kitchen, in-home laundry, air conditioning, Wi-Fi, a private backyard, and parking, providing a comfortable base for exploring local attractions like the Kia Centre and Camping World Stadium.
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.
Best pet friendly Winter Park, FL holiday rentals
Among the 288 accommodations in Winter Park, FL, here are the 4 best pet friendly rentals
9.2 7 reviews
Winter Park, FL
10/07 – 18/07
154 €/nighttotal: 1232 € (8 )
Cozy 2bd 2bth House Walk To Local Gems
2 4
house , Orlando
This Orlando house, situated 2.6km from the city centre and within 8km of Church Street Station, Camping World Stadium, and the Kia Center, offers convenient access to major attractions. This two-bedroom, two-bathroom property sleeps seven, boasting a fully equipped kitchen with dishwasher, a terrace, garden, free Wi-Fi, and free private parking; enjoy al fresco dining and proximity to local amenities.
Winter Park, FL
14/08 – 21/08
97 €/nighttotal: 679 € (7 )
15 Min Away From - Universal Studios! -Cozy Studio
1 2
studio , Orlando
This Orlando apartment is situated centrally, just an 8-minute drive from the Dr. Phillips Centre for the Performing Arts and the Kia Centre, with Universal's Epic Universe approximately 13.7 kilometres away and Disney 48.3 kilometres away. This pet-friendly studio apartment accommodates two guests and features air conditioning, complimentary WiFi in a private courtyard, and free parking, with coffee and tea provided.
10 90 reviews
Winter Park, FL
10/07 – 18/07
153 €/nighttotal: 1224 € (8 )
The Princeton- College Park’s Best Kept Secret!
2 4
bungalow , Orlando
This charming bungalow is situated in College Park, a peaceful neighbourhood just 16km from downtown Orlando and 37km from the theme parks. The property has consistently received excellent reviews for its location, cleanliness and overall experience. The home offers a comfortable living space for up to 5 guests, with a fully equipped kitchen and a spacious living area. You'll find everything you need for a relaxing stay, including a large TV with Netflix, high-speed Wi-Fi, a washing machine and dryer, and complimentary hot beverages.
8.0 1 review
Winter Park, FL
28/07 – 01/08
130 €/nighttotal: 520 € (4 )
Fireplace And Lake View Just 10 Minutes To Downtown Near Parks
2 2
house , Conway
This Orlando holiday home in Conway is located 9.3 kilometres from Church Street Station and 10.5 kilometres from Camping World Stadium, placing it 10 minutes from downtown Orlando attractions and 6.9 kilometres from Orlando International Airport. This 102 square metre cottage accommodates up to 7 guests across 2 bedrooms and 2 bathrooms, featuring a well-equipped kitchen with a fridge, microwave, and dishwasher, air conditioning, a garden, and Wi-Fi.