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

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3,414 Vacation rentals

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 $86 / night

$572 / week

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avg. 2 hours 19 minutes

from $86 / 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 $86 / night

$572 / week

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avg. 2 hours 19 minutes

from $86 / night

(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 $92 / night

$584 / week

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avg. 2 hours 19 minutes

from $92 / 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 $516 / night

$2,806 / week

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from $516 / 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 $164 / night

$1,145 / week

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avg. 1 hour 19 minutes

from $164 / 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 $149 / night

$1,042 / week

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from $149 / 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 $92 / night

$607 / week

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avg. 2 hours 19 minutes

from $92 / 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 $121 / night

$687 / week

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from $121 / 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 $92 / night

$584 / week

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avg. 2 hours 19 minutes

from $92 / night

29

Vacation studio in Winter Park

Central Florida / Winter Park

Studio 4 2 nights min

  • Studio
  • sleeps 4
  • 2 nights min
  • Child friendly
  • Pet friendly
Dear Future Guest, You'll be right in the heart of the eclectic, hipster-esque hub that is the Audubon Park Garden District. Find comfort & excitement in knowing you'll be staying in a neighborhood that won the National 2016 Great American Main Street Award! Our cute l …see more

from $100 / night

$659 / week

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from $100 / night

35

Winter Park Vacation villa rental

Central Florida / Winter Park

4 8 min stay varies

  • 4 bedrooms
  • sleeps 8
  • min stay varies
  • 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 $682 / night

$4,575 - $6,767 / week

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from $682 / 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 80 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 $102 / night

$665 / week

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from $102 / night

Great rentals within 20 miles that match your search

Distance approx 19.52 miles from Winter Park Show on Map

(9) Very Good 

45

Vacation villa rental

Central Florida / Kissimmee

4 8 4 nights min

  • 4 bedrooms
  • sleeps 8
  • 4 nights min
  • Beach/lakeside relaxation
  • Nearest beach 80 mi
  • Swimming pool
Whether you wish to hit the Theme Parks, go shopping at the Florida Mall or along International Drive, play some fantastic golf, or simply relax by the pool, this home is exactly what you are looking for. It is fully licensed and professionally managed through a conveni …see more

from $121 / night

$826 - $922 / week

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avg. 3 hours 30 minutes

from $121 / night

Distance approx 17.87 miles from Winter Park Show on Map

(1) Very Good 

20

Buena Ventura Lakes Vacation villa rental

Florida / Buena Ventura Lakes

4 8 min stay varies

  • 4 bedrooms
  • sleeps 8
  • min stay varies
  • Beach/lakeside relaxation
  • Nearest beach 105 mi
  • Swimming pool
Get your vacation started 15 minutes after leaving the airport when you stay in your private Regal Villa, an oasis of relaxation and fun. It's only 20 minutes straight down Osceola Parkway to Disney's gate, the same area as Universal Studios and Sea World. Just 1 hour's …see more

from $149 / night

$1,042 / week

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from $149 / night

Distance approx 12.87 miles from Winter Park Show on Map

(16) Excellent 

51

Penthouse rental in Orlando with golf nearby

Orlando / Vista Cay

3 8 3 nights min

  • 3 bedrooms
  • sleeps 8
  • 3 nights min
  • Beach/lakeside relaxation
  • Nearest beach 60 mi
  • Swimming pool
Stay in Orlando's Newest Five-Star Gated Community Vista Cay, located right next door to the Orange County Convention Center right by International Drive/Universal Blvd. Universal Studios, Sea World, and Disney are all within five to ten minute drive. In addition, Shing …see more

from $109 / night

$1,275 / week

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avg. 3 hours 2 minutes

from $109 / night

Distance approx 15.09 miles from Winter Park Show on Map

24

Apartment rental in Sanford

Central Florida / Sanford

2 6 3 nights min

  • 2 bedrooms
  • sleeps 6
  • 3 nights min
  • Child friendly
  • Air conditioning
Enjoy all the lively attractions and scenic beauty of this quaint Florida town from this 2-bedroom, 1-bathroom vacation rental apartment, which comfortably sleeps 6 in Sanford. This 2nd-story unit offers a beautiful, residential location, a handsome garden, patio and de …see more

from $172 / night

$1,203 / week

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avg. 9 minutes

from $172 / night

Distance approx 19.84 miles from Winter Park Show on Map

(8) Excellent 

11

Orlando Vacation apartment rental

Central Florida / Orlando

2 8 3 nights min

  • 2 bedrooms
  • sleeps 8
  • 3 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
Wyndham Bonnet Creek 9560 Via Encinas Lake Buena Vista, FL 32830 *** LAST MINUTE RESERVATIONS OK*** Wyndham Bonnet Creek Resort is mere minutes from the gates of Walt Disney World®. You’ll will enjoy a very rewarding stay on site. From the full activities calendar to s …see more

from $252 / night

$1,764 / week

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from $252 / night

Distance approx 18.36 miles from Winter Park Show on Map

32

Orlando Vacation condo rental

Central Florida / Orlando

1 4 7 nights min

  • 1 bedroom
  • sleeps 4
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
Disney's Saratoga Springs Resort & Spa is inspired by a historic New York retreat famous for its horse racing. Enjoy your Disney Vacation Club Villa and all of the amenities and recreational offerings available at this 65-acre Resort—just a short boat ride from Disney S …see more

from $229 / night

$1,603 / week

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from $229 / night

Distance approx 15.05 miles from Winter Park Show on Map

(1) Very Good 

5

Vacation condo with golf nearby in Orlando

Central Florida / Orlando

2 8 7 nights min

  • 2 bedrooms
  • sleeps 8
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
Two bedroom cono on International Drive in Orlando Florida. On-site restaurant, pools, golf, activities. Two minutes away from Sea World. Short drive to Disney World, Universal Studios, fine dining. Golf and tennis available on site. Activities and entertainment da …see more

from $295 / night

$2,061 / week

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from $295 / night

Distance approx 13.98 miles from Winter Park Show on Map

23

Vacation condo in Orlando

Central Florida / Orlando

3 12 4 nights min

  • 3 bedrooms
  • sleeps 12
  • 4 nights min
  • Child friendly
  • Pet friendly
Westgate Lakes is an expansive resort with so much to do when you're not exploring Orlando's surrounding theme parks. The rental condos were built on a huge lake with three separate nooks. Guests can grab a kayak or go on a thrilling speed boat ride along the water. Tak …see more

from $204 / night

$1,432 / week

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avg. 2 hours 27 minutes

from $204 / night

Distance approx 4.54 miles from Winter Park Show on Map

24

Vacation apartment in Lockhart

Florida / Lockhart

2 6 min stay varies

  • 2 bedrooms
  • sleeps 6
  • min stay varies
  • Child friendly
  • Air conditioning
A vacation to Orlando is exactly what your family needs! This newly remodeled 2-bedroom, 2-bathroom vacation rental condo that sleeps 6 is the perfect accommodation for your trip. The property features brand new furnishings, new kitchen appliances, updated bathrooms wit …see more

from $98 / night

$682 / week

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avg. 39 minutes

from $98 / night

Distance approx 16.81 miles from Winter Park Show on Map

(18) Very Good 

20

Orlando Vacation hotel apartment rental

Central Florida / Orlando

2 6 2 nights min

  • 2 bedrooms
  • sleeps 6
  • 2 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
Voted - the BEST Resort DEAL in Orlando (also Voted TOP 5 Resorts) Luxury Resort minutes from Disney & Universal Studios This is our 2BR Standard Villa Sleeps 6 - at the Grande Villas Resort and Cypress Pointe Resort (same property) with access to all resort ameni …see more

from $286 / night

$1,996 / week

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from $286 / night

Distance approx 14 miles from Winter Park Show on Map

(3) Very Good 

19

Vacation condo with shared pool in Orlando

Central Florida / Orlando

2 8 7 nights min

  • 2 bedrooms
  • sleeps 8
  • 7 nights min
  • Beach/lakeside relaxation
  • Nearest beach 101 mi
  • Swimming pool
Description • 2 Bedrooms with King Beds • 2 Queen Sleeper Sofa • 1 Full Kitchen, Dish Washer and Washer-Dryer • 2 Living rooms • Balcony • 1 Kitchenette Two-Bedroom,Two-Bathroom Villas offers remarkable spaciousness. It is furnished feature a king bed and whirlpoo …see more

from $246 / night

$1,718 / week

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from $246 / night

Distance approx 19.84 miles from Winter Park Show on Map

(1) Excellent 

6

Orlando Vacation villa rental

Central Florida / Orlando

2 8 3 nights min

  • 2 bedrooms
  • sleeps 8
  • 3 nights min
  • Swimming pool
  • Air conditioning
This is a luxury timeshare property in the heart of Disney. The property features 5 pools, 2 lazy rivers, 2 water slides, volleyball court, putt putt golf course and many activities for all ages. You do not need to go to Disney to be entertained. We also have access to …see more

from $308 / night

$2,156 / week

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avg. 1 hour 20 minutes

from $308 / night

Distance approx 19.68 miles from Winter Park

24

Home rental in Osteen

Florida / Osteen

4 8 3 nights min

  • 4 bedrooms
  • sleeps 8
  • 3 nights min
  • Child friendly
  • Air conditioning
Leisurely days and sunshine rays are ready to show you the best of Osteen at this newly updated 4-bedroom, 2-bath vacation rental house! Ideal for up to 8 travelers, this home boasts 1,828 square feet of high end living space and a private dock on St. Johns River. When …see more

from $201 / night

$1,403 / week

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avg. 39 minutes

from $201 / night

Distance approx 16.11 miles from Winter Park Show on Map

11

Vacation hotel apartment rental

Central Florida / Orlando

2 8 3 nights min

  • 2 bedrooms
  • sleeps 8
  • 3 nights min
  • Nearest beach 64 mi
  • Swimming pool
  • Child friendly
Located on Lake Eve and International Drive, the Fountains offers everything you would expect from a world-class resort as well as the convenience to Disney World. Besides Disney World, the Fountains has its own claim to fame, Wakoola Springs. This 75,000 square-foot t …see more

from $247 / night

$1,661 / week

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from $247 / night

Distance approx 19.84 miles from Winter Park Show on Map

(2) Very Good 

23

Vacation condo with golf nearby in Celebration

Central Florida / Celebration

2 8 7 nights min

  • 2 bedrooms
  • sleeps 8
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
BONNET CREEK RESORT CLOSEST TO DISNEY One mile from Downtown Disney Wyndham Bonnet Creek Resort Within the Disney World® Complex 2 Bedroom 2 Bath Deluxe Condo ~ sleeps 8 My family stays here at least 6 times a year!! It's just …see more

from $278 / night

$1,946 / week

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avg. 3 hours 15 minutes

from $278 / night

Distance approx 17.01 miles from Winter Park Show on Map

27

Orlando Vacation villa rental

Central Florida / Orlando

2 6 7 nights min

  • 2 bedrooms
  • sleeps 6
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
Rent Price: Neg. Currency United States Dollar (USD) Base Tax Rate 13.000% Minimum Stay 7 Nights Nightly Rate $248 USD Weekly Rate $1754 USD Weekend Rate $250 USD Monthly Rate $7000 USD Bedrooms: 2 Bathrooms: 2 Week #: Floating Usage: Annual Unit Number: …see more

from $284 / night

$2,009 / week

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from $284 / night

Distance approx 16.81 miles from Winter Park Show on Map

23

Orlando Vacation condo rental

Central Florida / Orlando

2 6 7 nights min

  • 2 bedrooms
  • sleeps 6
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
Fixed week rental, 7 nights blocks only, Fri/Sat/Sun check in / changeover only. Guest Accommodation Information Relax in the comfort of this 2-Bedrooms accommodation featuring sumptuous sleeping arrangements and a full bathroom complete with complimentary amenities. …see more

from $193 / night

$1,346 - $1,460 / week

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from $193 / night

Distance approx 15.07 miles from Winter Park Show on Map

9

Vacation condo with shared pool in Kissimmee

Central Florida / Kissimmee

1 4 4 nights min

  • 1 bedroom
  • sleeps 4
  • 4 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
The name of the resort is Vacation Village at Parkway. This resort in Kissimmee brings all the comforts you'd want in a deluxe suite accommodation. It offers six swimming pools to cool off after a day at the exciting local attractions, a picnic area, and lots to do if y …see more

from $155 / night

$687 / week

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avg. 2 hours 33 minutes

from $155 / night

Distance approx 14.3 miles from Winter Park Show on Map

(1) Very Good 

7

Townhouse rental in Orlando

Central Florida / Orlando

2 6 3 nights min

  • 2 bedrooms
  • sleeps 6
  • 3 nights min
  • Child friendly
  • Air conditioning
  • Pet friendly
This delightful townhome has a Master Bedroom on the first floor with full bath and queen sized bed. Upstairs is a very large bedroom with two more queen beds and another full bath. There's a lovely patio with table and chairs and also a balcony upstairs for pleasant o …see more

from $121 / night

$802 / week

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from $121 / night

Distance approx 16.07 miles from Winter Park Show on Map

34

Vacation apartment rental

Central Florida / Orlando

3 8 2 nights min

  • 3 bedrooms
  • sleeps 8
  • 2 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
Enjoy the convenience of having a crystal blue swimming pool with lounging and BBQ areas, gym access, business center and games room, all in one luxury residential complex that is very near all three Orlando theme parks. Look no further than this clean, calm and comfort …see more

from $161 / night

$1,123 / week

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from $161 / night

Distance approx 16.27 miles from Winter Park Show on Map

9

Vacation townhouse with shared pool in Buena Ventura Lakes

Florida / Buena Ventura Lakes

3 6 4 nights min

  • 3 bedrooms
  • sleeps 6
  • 4 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
Beautiful and comfortable townhouse, very comfortable for people who come to vacation in Central Florida and wants their prestado render, is a spacious property with a private pool, 3 bedrooms, dining room, living room and large kitchen. Here you can enjoy beautiful ex …see more

from $115 / night

$859 / week

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from $115 / night

Distance approx 19.84 miles from Winter Park Show on Map

14

Condo rental in Celebration

Central Florida / Celebration

2 8 7 nights min

  • 2 bedrooms
  • sleeps 8
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
Escape to the essence of Mediterranean indulgence and relaxation at Wyndham Bonnet Creek Resort, located adjacent to Walt Disney World ® Resort. This gorgeous European inspired vacation resort offers everything you need for an unforgettable Disney retreat. Indulge in on …see more

from $395 / night

$2,577 / week

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avg. 2 hours 44 minutes

from $395 / night

Distance approx 10.98 miles from Winter Park Show on Map

4

Orlando Vacation condo rental

Central Florida / Orlando

2 8 7 nights min

  • 2 bedrooms
  • sleeps 8
  • 7 nights min
  • Child friendly
Orlando’s Sunshine Resort is located within minutes of Universal Studios®, SeaWorld®, and Walt Disney World®. If you wish a relaxing day, you may, read a book in the comfort of your screened-in porch, soak in the Florida sun by the pool or organize a showdown on the s …see more

from $246 / night

$1,718 / week

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from $246 / night

Distance approx 16.99 miles from Winter Park Show on Map

9

Orlando Vacation villa rental

Central Florida / Orlando

2 6 7 nights min

  • 2 bedrooms
  • sleeps 6
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Car not necessary
Bluetree Resort 12007 Cypress Run Rd. Lake Buena Vista, FL 32836 Two Bedroom 2 bath sleep 6 Full Kitchen Sat-Sat Sun-Sun 7 nights Only $875 2 villas available = $1600 1 villa $850 AMENETIES 4 Swimming pools -- 3 heated Children's pool Game room Playground BBQ Grill …see more

from $155 / night

$1,082 / week

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from $155 / night

Distance approx 19.52 miles from Winter Park Show on Map

22

Kissimmee Vacation villa rental

Central Florida / Kissimmee

5 12 6 nights min

  • 5 bedrooms
  • sleeps 12
  • 6 nights min
  • Swimming pool
  • Child friendly
  • Car not necessary
This spectacular Orlando vacation rental villa is bright, spacious and designed for relaxation in your next vacation in Orlando. Featuring 5 bedrooms, 5 bathrooms It’s well suited to larger families or groups of friends. Throughout this Florida vacation home, you’ …see more

from $509 / night

$3,559 / week

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avg. 3 hours 56 minutes

from $509 / night

Distance approx 19.36 miles from Winter Park Show on Map

76

Vacation villa with swimming pool, golf nearby in Celebration

Central Florida / Celebration

8 20 min stay varies

  • 8 bedrooms
  • sleeps 20
  • min stay varies
  • Swimming pool
  • Car not necessary
p class="rtejustifyStorey Lake - Kissimmee is a brand new vacation community located just 4 miles from the magical world of Disney and just minutes to Universal, Sea World and the many water parks in the area. Central Florida is also home to some of the nation's top-rat …see more

from $1,886 / night

$12,632 / week

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avg. 3 hours 56 minutes

from $1,886 / night

Distance approx 19.28 miles from Winter Park Show on Map

16

Vacation log cabin with swimming pool in Celebration

Central Florida / Celebration

4 8 min stay varies

  • 4 bedrooms
  • sleeps 8
  • min stay varies
  • Swimming pool
  • Child friendly
  • Car not necessary
Welcome to the gated resort community of Storey Lake. A new community in Kissimmee - this will have all you want and more. This gorgeous 4 bedroom and 3 bathroom home sleeps you and 7 guests perfectly. With all the amenities of home, you will feel at ease and ready for …see more

from $176 / night

$1,227 - $2,734 / week

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Responds fast!
avg. 2 hours 36 minutes

from $176 / night

Distance approx 19.19 miles from Winter Park Show on Map

18

Vacation home with swimming pool in Kissimmee

Central Florida / Kissimmee

5 11 min stay varies

  • 5 bedrooms
  • sleeps 11
  • min stay varies
  • Swimming pool
  • Car not necessary
div class="rtejustifyIf you are ready for some Florida fun, come on down to this beautiful vacation home located in Storey Lake. This townhouse has reached the coveted Grand Collection status. This means it is expertly designed and beautifully decorated with the comfort …see more

from $198 / night

$1,387 - $3,118 / week

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from $198 / night