10 Best Vacation Rentals in Winter Park - Holiday Lettings - Cabins

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3,231 Vacation rentals

(2) Excellent 

27

Vacation home rental

Central Florida / Winter Park

1 2 3 nights min

  • 1 bedroom
  • sleeps 2
  • 3 nights min
  • Nearest beach 100 mi
  • Suitable for children age 5+
  • Air conditioning
Comfortable 1bd/1bath home with convenient location midway between historic Winter Park and Downtown Orlando. Just a hop away from I-4. Within close distance you will find a unique selection of specialty shops, parks, and restaurants for every taste on Edgewater Dr.. …see more

from $80 / night

$510 / week

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avg. 1 hour 24 minutes

from $80 / night

(3) Very Good 

22

Winter Park Vacation home rental

Central Florida / Winter Park

1 2 2 nights min

  • 1 bedroom
  • sleeps 2
  • 2 nights min
  • Nearest beach 100 mi
  • Child friendly
  • Air conditioning
Your own private unit includes 1 master bedroom with Queen bed Full Kitchen with stove, refrigerator, microwave, coffee maker 32" flat screen tv. Access to Washer/dryer Comfortable & Clean 1bd/1bath home with convenient location in historic Winter Park yet very close t …see more

from $80 / night

$530 / week

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Responds fast!
avg. 1 hour 24 minutes

from $80 / night

(2) Excellent 

13

Vacation home in Winter Park

Central Florida / Winter Park

2 5 7 nights min

  • 2 bedrooms
  • sleeps 5
  • 7 nights min
  • Nearest beach 88 mi
  • Child friendly
  • Air conditioning
Furnished with original furniture from the 1950's era in a home built in 1955 with original wood floors, bathroom tile, plaster walls and kitchen cabinetry. Clean lines, simple and comfortable. FURNISHED Mid Century Modern Short/Long term rental located in Olde Winter …see more

from $143 / night

$1,000 / week

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from $143 / night

37

Vacation home with golf nearby in Winter Park

Central Florida / Winter Park

1 2 2 nights min

  • 1 bedroom
  • sleeps 2
  • 2 nights min
  • Nearest beach 60 mi
  • Child friendly
  • Air conditioning
Comfortable & Clean 1bd/1bath home with convenient location in historic Winter Park yet very close to Downtown Orlando or the main interstate to get you anywhere quickly. Beautiful Mead Gardens is a block down the road and is no cost to park and walk the gardens or picn …see more

from $75 / night

$499 / week

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Responds fast!
avg. 1 hour 24 minutes

from $75 / night

27

Vacation home in Winter Park

Central Florida / Winter Park

1 2 2 nights min

  • 1 bedroom
  • sleeps 2
  • 2 nights min
  • Nearest beach 100 mi
  • Child friendly
  • Air conditioning
Your own private unit includes 1 master bedroom with Queen bed Full Kitchen with stove, refrigerator, microwave, coffee maker 32" flat screen tv. Access to Washer/dryer Comfortable & Clean 1bd/1bath home with convenient location in historic Winter Park yet very close t …see more

from $75 / night

$499 / week

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Responds fast!
avg. 1 hour 24 minutes

from $75 / night

11

Vacation home rental

Central Florida / Winter Park

3 5 1 night min

  • 3 bedrooms
  • sleeps 5
  • 1 night min
  • Nearest beach 30 mi
  • Child friendly
  • Air conditioning
The first thing you notice when you walk into this tiny house is how spacious it is. A beautiful view of the lake is is framed by a picture window. The couch is inset into a "window-box" where you can let your troubles melt away. Relax outside on your teak chairs only …see more

from $105 / night

$600 / week

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from $105 / night

(2) Good 

20

Winter Park Vacation home rental

Central Florida / Winter Park

1 2 3 nights min

  • 1 bedroom
  • sleeps 2
  • 3 nights min
  • Nearest beach 100 mi
  • Child friendly
  • Air conditioning
This is a great little neighborhood chock full of local businesses, great people, nice neighbors and just a nice homey feeling. I can't get enough of the Main Street (Edgewater Dr.) running through, you have everything from some pretty great restaurants, plenty of yoga …see more

from $80 / night

$510 / week

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Responds fast!
avg. 1 hour 24 minutes

from $80 / night

35

Vacation home rental

Central Florida / Winter Park

3 6 3 nights min

  • 3 bedrooms
  • sleeps 6
  • 3 nights min
  • Beach/lakeside relaxation
  • Nearest beach 81 mi
  • Child friendly
A beautifully appointed 3 bedroom cottage on 400 acre Lake Fairview. We are central to College Park, Winter Park, and Altamonte Springs giving you the most comprehensive selection of shopping, eateries, and theater selections available in Orlando. Just minutes from fr …see more

from $350 / night

$2,450 / week

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from $350 / night

35

Winter Park Vacation villa rental

Central Florida / Winter Park

4 8 4 nights min

  • 4 bedrooms
  • sleeps 8
  • 4 nights min
  • Child friendly
  • Air conditioning
  • Private garden
Lakeside, on the shores of Lake Killarney, is in the exclusive village town of Winter Park (32789). You are 7 min to downtown Orlando, 20 min to Universal/ Disney. A 5,700 sq. ft family estate home with 285 ft of shoreline situated in an eco-sanctuary of rare birds & …see more

from $595 / night

$3,995 / week

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from $595 / night

10

Townhouse rental in Winter Park

Central Florida / Winter Park

2 6 2 nights min

  • 2 bedrooms
  • sleeps 6
  • 2 nights min
  • Child friendly
You’ll love this place! Recent renovations makes this mid-century modern cottage feel like a dream and you can't beat the location! Smart TVs (no cable). Modern furniture, full kitchen with Quartz counter tops and Slate appliances. Everything is less than 2 years old. …see more

from $120 / night

$840 / week

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from $120 / night

9

Vacation guest house in Winter Park

Central Florida / Winter Park

1 2 3 nights min

  • 1 bedroom
  • sleeps 2
  • 3 nights min
  • Air conditioning
  • Private garden
Enjoy our guest house in our back yard with your private entrance. We are in Winter Park where you are minutes away from the Park Ave strip and Winter Park Village with a car. Make this your home away from home while in town. The studio was fully furnished in late 2015 …see more

from $90 / night

$550 / week

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Responds fast!
avg. 37 minutes

from $90 / night

14

Winter Park Vacation home rental

Central Florida / Winter Park

1 5 1 night min

  • 1 bedroom
  • sleeps 5
  • 1 night min
  • Nearest beach 10 mi
  • Child friendly
  • Air conditioning
Just because it's a tiny house doesn't mean you have to skimp on style! With an open floor plan and high ceilings, this tiny home is filled with light and air. The Ritz has high-end finishes, including a full-size, stainless steel fridge, glass stove cooktop and Italian …see more

from $89 / night

$580 / week

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from $89 / night

18

Vacation home in Winter Park

Central Florida / Winter Park

8 18 min stay varies

  • 8 bedrooms
  • sleeps 18
  • min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
Top Villas does vacation rentals differently. Book with us and youll get the best homes, at the best prices, from people who really care. Best rate guarantee | Tailor-made service | 24/7 guest support Key features 8 bedrooms 5 bathrooms Sleeps 18 Private pool Game …see more

from $295 / night

$2,065 / week

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Responds fast!
avg. 1 hour 48 minutes

from $295 / night