10 Best Winter Garden Apartments on Holiday Lettings - Vacation rentals

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14,617 Vacation rentals

(3) Excellent 

25

Winter Garden Vacation home rental

Central Florida / Winter Garden

3 6 7 nights min

  • 3 bedrooms
  • sleeps 6
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
Our three bedroom, two bathroom home sleeps up to 6 people and is in Vista del Lago. This is a beautiful and tranquil gated community off the 192 within 10 minutes drive from Disney and all the attractions. The fully furnished lounge/diner has tv with Netflix. The full …see more

from $82 / night

$570 - $666 / week

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Responds fast!
avg. 1 hour 34 minutes

from $82 / night

17

Vacation apartment with shared pool in Winter Garden

Central Florida / Winter Garden

2 6 min stay varies

  • 2 bedrooms
  • sleeps 6
  • min stay varies
  • Swimming pool
  • Ask about children
  • Air conditioning
Property Description: Palisades Vacations offers Vacation Suites at the well-known Palisades Resort located near the West Gate of Walt Disney World. The area is in a natural and peaceful setting but close to all of the local attractions and seven world class golf course …see more

from $78 / night

$545 / week

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from $78 / night

(2) Excellent 

16

Home rental in Winter Garden

Central Florida / Winter Garden

3 7 1 night min

  • 3 bedrooms
  • sleeps 7
  • 1 night min
  • Swimming pool
  • Child friendly
  • Air conditioning
Disney/Universal/SeaWorld Vacation - Vista del Lago 3 bed / 2 bath Vacation Rental - At 2000 square feet, my home offers 3 Bedrooms with 2 full Baths. The living room offers a 60 inch HDTV for your family viewing pleasure after a day at the parks. The open floor plan …see more

from $91 / night

$652 / week

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Responds fast!
avg. 3 hours 17 minutes

from $91 / night

6

Home rental in Winter Garden

Central Florida / Winter Garden

4 8 3 nights min

  • 4 bedrooms
  • sleeps 8
  • 3 nights min
  • Child friendly
This newly listed & furnished beautiful single family home has over 2000sq ft. 24 hour gated 'all age community' off Route 192. Approximate travel time to attractions: Orlando International Airport - approximately 30 minutes Disney World - 10 minutes Universal Studi …see more

from $144 / night

$859 / week

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from $144 / night

(18) Excellent 

Certificate of Excellence

11

Vacation villa in Winter Garden

Central Florida / Winter Garden

3 8 4 nights min

  • 3 bedrooms
  • sleeps 8
  • 4 nights min
  • Child friendly
  • Air conditioning
A large, luxury, fully air conditioned, 3 bedroom, 2 bathroom villa, with free, fast Wi Fi. 24 hour security guard on a gated complex. Filtered water tap, no need to buy bottled water as you can refill your own bottles and use the cool bags for the parks. For everyo …see more

Certificate of Excellence

from $111 / night

$592 - $636 / week

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Responds fast!
avg. 3 hours 42 minutes

from $111 / night

20

Vacation home with shared pool in Winter Garden

Central Florida / Winter Garden

3 6 3 nights min

  • 3 bedrooms
  • sleeps 6
  • 3 nights min
  • Beach/lakeside relaxation
  • Swimming pool
  • Child friendly
Charming Villa just 4 miles from Disney and minutes from other area attractions. Fully furnished 3 bedroom (king, queen & full beds), 2 bathroom home in a gated community for your security. In addition to the lovely home you have access to 3 pools, 2 jacuzzi's, playgrou …see more

from $77 / night

$494 / week

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from $77 / night

(1) Excellent 

18

Camper van accommodation in Winter Garden

Central Florida / Winter Garden

3 8 3 nights min

  • 3 bedrooms
  • sleeps 8
  • 3 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
Stay only 5 miles from Disney World gates. High quality and modern furnishings greet you at Buckeye Butterfly Villa with a touch of elegance and panache. You will not be disappointed in our recently refurbished 3 bedroom/2 bath home. With one of 3 community pool …see more

from $144 / night

$911 / week

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Responds fast!
avg. 2 hours 14 minutes

from $144 / night

(2) Very Good 

8

Vacation home in Winter Garden

Central Florida / Winter Garden

3 8 5 nights min

  • 3 bedrooms
  • sleeps 8
  • 5 nights min
  • Child friendly
  • Air conditioning
Our three bedroom property is situated in Vista del Lago, a beautiful lakeside residential community on Highway 192 and just 6 miles West of Disney and an hour from Sanford Airport and about 35-40 mins from Orlando International Airport. It is within easy reach o …see more

from $97 / night

$629 / week

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from $97 / night

10

Vacation condo in Winter Garden

Central Florida / Winter Garden

2 6 3 nights min

  • 2 bedrooms
  • sleeps 6
  • 3 nights min
  • Child friendly
Set on 64 acres of lush landscape, Liki Tiki Village is located in the heart of Orlando’s tourist district. The family-friendly resort includes a lagoon with five water slides, water volcano, toddler’s play area and dancing fountain. Accommodations include a full kitche …see more

from $224 / night

$1,563 / week

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Responds fast!
avg. 3 hours 42 minutes

from $224 / night

13

Vacation apartment rental

Central Florida / Winter Garden

3 6 min stay varies

  • 3 bedrooms
  • sleeps 6
  • min stay varies
  • Swimming pool
  • Ask about children
  • Air conditioning
Property Description: Palisades Vacations offers Vacation Suites at the well-known Palisades Resort located near the West Gate of Walt Disney World. The area is in a natural and peaceful setting but close to all of the local attractions and seven world class golf course …see more

from $78 / night

$545 / week

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from $78 / night

14

Winter Garden Vacation apartment rental

Central Florida / Winter Garden

2 6 min stay varies

  • 2 bedrooms
  • sleeps 6
  • min stay varies
  • Swimming pool
  • Ask about children
  • Air conditioning
Property Description: Palisades Vacations offers Vacation Suites at the well-known Palisades Resort located near the West Gate of Walt Disney World. The area is in a natural and peaceful setting but close to all of the local attractions and seven world class golf course …see more

from $78 / night

$545 / week

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from $78 / night

Great rentals within 20 miles that match your search

Distance approx 15.94 miles from Winter Garden Show on Map

(8) Very Good 

Certificate of Excellence

20

Vacation townhouse in Kissimmee

Kissimmee / Encantada Resort

4 10 5 nights min

  • 4 bedrooms
  • sleeps 10
  • 5 nights min
  • Child friendly
  • Air conditioning
This is the Encantada Resort Condo in a beautiful short term rental gated development. Heated Pool attached to condo plus resort pool with all amenities. Very close to Disney and all attractions. Includes all kitchen utensils, appliances and washer dryer. Has WiFi and f …see more

Certificate of Excellence

from $155 / night

$945 / week

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Responds fast!
avg. 1 hour 2 minutes

from $155 / night

Distance approx 13.39 miles from Winter Garden

(33) Excellent 

Certificate of Excellence

47

Vacation villa with swimming pool in Orlando

Central Florida / Orlando

4 8 7 nights min

  • 4 bedrooms
  • sleeps 8
  • 7 nights min
  • Nearest beach 129 mi
  • Swimming pool
  • Child friendly
A lovely, spacious family friendly villa located in the popular community of Orange Tree - ONLY A 15 MINUTE DRIVE TO DISNEY! A SPACIOUS , FAMILY FRIENDLY VILLA ON A LARGE CORNER PLOT WITH A SOUTH FACING POOL AND SUNNY POOL DECK. Our spacious and relaxing villa is air …see more

Certificate of Excellence

from $117 / night

$878 - $1,173 / week

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Responds fast!
avg. 1 hour 29 minutes

from $117 / night

Distance approx 12.69 miles from Winter Garden

(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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Responds fast!
avg. 3 hours 2 minutes

from $109 / night

Distance approx 18.44 miles from Winter Garden

(5) Excellent 

16

Villa rental in Kissimmee

Kissimmee / Indian Ridge

3 6 7 nights min

  • 3 bedrooms
  • sleeps 6
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
Solar heated south facing pool, a partly fenced garden with a forested area to the rear providing privacy. The pool is fully screened and equipped with a range of upholstered poolside furniture and a lanai for shade. All doors to the pool area are double locked and al …see more

from $141 / night

$961 - $1,139 / week

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from $141 / night

Distance approx 16.46 miles from Winter Garden

(7) Very Good 

19

Villa rental in Kissimmee with swimming pool

Kissimmee / Emerald Isle Kissimmee

5 12 min stay varies

  • 5 bedrooms
  • sleeps 12
  • min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
This 5 bed villa is located in the sought after resort of Emerald Island. It appeals to visitors because it is so close to Disney and it has a lively Clubhouse. Here you find the community pool, tikki bar, fitness and theatre rooms. The home itself is on one level and h …see more

from $133 / night

$915 - $1,445 / week

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Responds fast!
avg. 3 hours 6 minutes

from $133 / night

Distance approx 16.67 miles from Winter Garden

(3) Excellent 

18

Vacation villa rental

Central Florida / Kissimmee

4 8 min stay varies

  • 4 bedrooms
  • sleeps 8
  • min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
Our holiday home is in the perfect location for a fantastic family vacation, only four miles from the Disney parks and within easy reach of golf courses, shops and restaurants. In a sunny corner of the award-winning Emerald Island Resort, which for peace of mind is gate …see more

from $163 / night

$885 - $1,069 / week

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from $163 / night

Distance approx 14.58 miles from Winter Garden

21

Vacation home with swimming pool in Four Corners

Central Florida / Four Corners

5 12 7 nights min

  • 5 bedrooms
  • sleeps 12
  • 7 nights min
  • Swimming pool
  • Car not necessary
Property Type: House with Private Pool Floor Area: 2000 sq ft Location: Greater Groves, Clermont, Disney Area Professionally managed and fully furnished vacation home property with Private Pool.. This property has the equipment to provide your family with all the comfor …see more

from $241 / night

$1,684 / week

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Responds fast!
avg. 3 hours 50 minutes

from $241 / night

Distance approx 19.49 miles from Winter Garden

41

Kissimmee Vacation townhouse rental

Central Florida / Kissimmee

3 7 1 night min

  • 3 bedrooms
  • sleeps 7
  • 1 night min
  • Swimming pool
  • Child friendly
  • Air conditioning
The main floor master bedroom has a King size bed,TV,a corner office,plenty of closet space and an attachement ensuite bath with a large tub Jacuzzi jets . The second floor has 2 roomy bedrooms and a separate bath. The kitchen is equiped with dishwasher,microwave,oven,i …see more

from $114 / night

$794 / week

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from $114 / night

Distance approx 16.7 miles from Winter Garden

54

Four Corners Vacation home rental

Central Florida / Four Corners

8 20 min stay varies

  • 8 bedrooms
  • sleeps 20
  • min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
8 bd Glorious Vacation Home, pond view/heated pool/spa/WIFI Gated Resort Community, one of best resort at Disney area Free Wireless Internet Gas bbq grill Spa Games room Sleeps 20 5 King Size beds 1 Queen size beds 2 Twins (single) beds 2 Sets bunk beds 2 Cribs Emerald …see more

from $217 / night

$1,488 - $3,091 / week

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Responds fast!
avg. 3 hours 8 minutes

from $217 / night

Distance approx 16.21 miles from Winter Garden

5

Kissimmee Vacation villa rental

Central Florida / Kissimmee

1 4 7 nights min

  • 1 bedroom
  • sleeps 4
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
Just 1 Mile from Walt Disney World Kissimmee Resort! Westgate Town Center Resort & Spa provides guests all the comforts of a fully furnished home just 1 mile from Walt Disney World® Resort and minutes from other Orlando area attractions. With a variety of accommodation …see more

from $328 / night

$2,290 / week

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from $328 / night

Distance approx 19.63 miles from Winter Garden

(2) Excellent 

30

Vacation home in Kissimmee

Central Florida / Kissimmee

4 8 3 nights min

  • 4 bedrooms
  • sleeps 8
  • 3 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
This fabulous home is waiting for you to make this your home away from home! Come enjoy the Florida sun in your own private pool . Your family will love this home with your own fully equipped kitchen, Complimentary Wi-Fi! And for those days you want to skip the parks, e …see more

from $126 / night

$882 / week

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from $126 / night

Distance approx 16.66 miles from Winter Garden

(3) Very Good 

53

Vacation apartment rental

Central Florida / Kissimmee

3 6 min stay varies

  • 3 bedrooms
  • sleeps 6
  • min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
In sunny Orlando/Kissimmee Florida, location is everything.....and we are located the very closest to Disney......less than two miles to the main entrance! Each evening, you may enjoy the breath taking view of Disney Fireworks from the Windsor Hills Resort area. We are …see more

from $109 / night

$762 - $954 / week

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Responds fast!
avg. 2 hours 17 minutes

from $109 / night

Distance approx 17.88 miles from Winter Garden

10

Davenport Vacation home rental

Central Florida / Davenport

5 10 min stay varies

  • 5 bedrooms
  • sleeps 10
  • min stay varies
  • Swimming pool
  • Ask about children
  • Air conditioning
'THE CORNER HOUSE' HIGHGATE PARK LUXURY 5 BED VILLA WITH SOUTH WEST FACING POOL. Private, Quiet and Secure Location, No rear neighbours.Thank you for viewing our home, The villa is situated on the exclusive Highgate Park gated community which includes a tennis court and …see more

from $212 / night

$1,483 / week

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from $212 / night

Distance approx 19.27 miles from Winter Garden

30

Vacation villa with golf nearby in Davenport

Central Florida / Davenport

7 16 min stay varies

  • 7 bedrooms
  • sleeps 16
  • min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
Private Pool - Billiard table - Game room - Cinema room projector with cable TV & Blu-ray DVD player (with Netflix and Pandora apps for your own subscriptions )- Cable TV HBO, Cinemax, Showtime, Starz, Epix, Encore, Flix. They work on TV, On Demand, and Online. Over …see more

from $194 / night

$1,355 / week

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Responds fast!
avg. 1 hour 57 minutes

from $194 / night

Distance approx 13.23 miles from Winter Garden

(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 19.69 miles from Winter Garden

22

Vacation home in Davenport

Central Florida / Davenport

4 8 min stay varies

  • 4 bedrooms
  • sleeps 8
  • min stay varies
  • Ask about children
This charming, air conditioned, 4 bedroom/ 3-bath home sleeps eight and has recently been refurnished and professionally decorated. The villa is conveniently located minutes from Disney, golf courses and some of the citys best shopping malls. It is also within an hours …see more

from $138 / night

$962 / week

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from $138 / night

Distance approx 18.86 miles from Winter Garden

24

Vacation villa with swimming pool in Four Corners

Central Florida / Four Corners

5 12 min stay varies

  • 5 bedrooms
  • sleeps 12
  • min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
Snowbirds rejoice as your quintessential Sunshine State retreat awaits you at this 5-bedroom, 3-bath Davenport vacation rental villa! Located in the desirable Highlands Reserve Golf Club, this 2-story family home is the dream Disney destination for up to 12 travelers. H …see more

from $149 / night

$1,042 / week

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Responds fast!
avg. 9 minutes

from $149 / night

Distance approx 13.3 miles from Winter Garden

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 13.23 miles from Winter Garden

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 15.56 miles from Winter Garden

24

Vacation apartment with shared pool in Four Corners

Central Florida / Four Corners

4 8 min stay varies

  • 4 bedrooms
  • sleeps 8
  • min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
Discover the perfect Disney retreat while staying at this 4-bedroom, 2.5-bathroom Kissimmee vacation rental condo! The property welcomes 8 guests to experience the entertainment and excitement of Disney, Universal and all of the other amazing theme parks nearby. Dine at …see more

from $126 / night

$882 - $1,355 / week

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Responds fast!
avg. 9 minutes

from $126 / night

Distance approx 14.21 miles from Winter Garden

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 19.49 miles from Winter Garden

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 16.52 miles from Winter Garden

31

Home rental in Four Corners

Central Florida / Four Corners

6 12 4 nights min

  • 6 bedrooms
  • sleeps 12
  • 4 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
Huge home, overlooking conservation woodlands! Large pool and spa, with deck space, that receives sunlight all day. FREE welcome food pack for all our guests! Quiet, private home for families big or small! Sleeps 12, Large 30ft pool 6 person spa! Free Wifi, bring your o …see more

from $310 / night

$2,164 / week

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from $310 / night

Distance approx 19.1 miles from Winter Garden

22

Vacation villa with swimming pool in Four Corners

Central Florida / Four Corners

5 10 5 nights min

  • 5 bedrooms
  • sleeps 10
  • 5 nights min
  • Swimming pool
  • Child friendly
  • Car not necessary
div class="rtejustifyAbout our Villa and Location The prestigious Highlands Reserve Golf & Leisure Community is the location of our truly luxurious executive villa. This much sought after location is ideal, be it the fun and excitement of the many theme parks or the cha …see more

from $289 / night

$2,020 / week

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from $289 / night

Distance approx 13.27 miles from Winter Garden

17

Home rental in Clermont with swimming pool

Lake County / Clermont

4 8 2 nights min

  • 4 bedrooms
  • sleeps 8
  • 2 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
Looking for the perfect home to make your vacation unforgettable? Then look no further than this 4 bedroom, 3 bathroom vacation home located in the quiet community of Orange Tree on Highway 27 in Clermont. This home is located only a few minutes away from the Four …see more

from $121 / night

$796 / week

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Responds fast!
avg. 5 minutes

from $121 / night

Distance approx 16.51 miles from Winter Garden

34

Four Corners Vacation home rental

Central Florida / Four Corners

5 12 7 nights min

  • 5 bedrooms
  • sleeps 12
  • 7 nights min
  • Swimming pool
  • Car not necessary
8120 Pomo Drive Kissimmee, FL 34747 - 2303IC Property Type: House with Private Pool Floor Area: 2136 sq ft Location: Indian Creek,Kissimmee, Disney Area Professionally managed and fully furnished vacation home property with Private Pool.. Our property ha …see more

from $248 / night

$1,732 / week

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Responds fast!
avg. 3 hours 56 minutes

from $248 / night

Distance approx 17.79 miles from Winter Garden

75

Four Corners Vacation home rental

Central Florida / Four Corners

9 20 7 nights min

  • 9 bedrooms
  • sleeps 20
  • 7 nights min
  • Swimming pool
  • Car not necessary
Beautiful home with game room, jacuzzi, BBQ grill and much more!! Property Type: 9 Bedrooms, 6 Baths Home with Private Pool and Jacuzzi Floor Area: 4382 sq. ft. Location: Windsor at Westside Resort, Disney Area  This Beautiful Property is located in Windsor at Westsi …see more

from $803 / night

$5,619 / week

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from $803 / night

Distance approx 16.7 miles from Winter Garden

29

Kissimmee Vacation home rental

Central Florida / Kissimmee

4 10 7 nights min

  • 4 bedrooms
  • sleeps 10
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
Brand new to us - Just started renting August 2015. Beautiful, like new, 4 bedroom / 3 bathroom home with an luxury feel. Sleeps 8-10. Beachy decor. 2 master suites (one king / one queen) both with private bathrooms. 2 twin bedrooms / 2 twin beds each share the 3rd bath …see more

from $246 / night

$1,718 / week

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Responds fast!
avg. 1 hour 27 minutes

from $246 / night

Distance approx 17.56 miles from Winter Garden

26

Condo rental in Old Town

Florida / Old Town

1 4 1 night min

  • 1 bedroom
  • sleeps 4
  • 1 night min
  • Swimming pool
  • Child friendly
  • Air conditioning
Star Island Resort & Club is set on the banks of a private lake, Lake Cecile, this resort is 4.8 miles from Disney. There are 2 outdoor pools & a hot tub, plus 9 tennis courts, a driving range & a putting green. Other amenities include WiFi, a spa, a fitness center & a …see more

from $149 / night

$1,042 / week

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from $149 / night