Vacation Rentals & Villas in Winter Garden

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16,226 villas

6

'Last Min. Thanksgiving Special' 5 Star Vacation Home Near Attractions

Central Florida / Winter Garden

Winter Garden house

4 8 3 nights min

  • 4 bedrooms
  • sleeps 8
  • 3 nights min
  • Child Friendly

Price per night from

$144

Price per night from

$144

(2) Excellent 

16

Sun, Fun and Amusement Parks - $99/Night

Central Florida / Winter Garden

Winter Garden house

3 7 1 night min

  • 3 bedrooms
  • sleeps 7
  • 1 night min
  • Swimming pool
  • Child Friendly
  • Air conditioning

Price per night from

$91

Responds fast!
avg. 3 hours 17 minutes

Price per night from

$91

17

Ann's Palisades Condo

Central Florida / Winter Garden

Winter Garden apartment

2 6 min stay varies

  • 2 bedrooms
  • sleeps 6
  • min stay varies
  • Swimming pool
  • Ask about children
  • Air conditioning

Price per night from

$78

Price per night from

$78

(18) Excellent 

Certificate of Excellence

11

Florida Private Villa 4 miles to Disney inc Wi Fi

Central Florida / Winter Garden

Winter Garden villa

3 8 4 nights min

  • 3 bedrooms
  • sleeps 8
  • 4 nights min
  • Child Friendly
  • Air conditioning
“Great vacation home!” I enjoyed very much this Villa: gated community, comfortable, clean, and everything you can think of for a vacation stay. It's near to Disney World, supermarket, and restaurants. Jancis is great and responsive for any questions,
…see more

Certificate of Excellence

Price per night from

$111

Responds fast!
avg. 3 hours 42 minutes

Price per night from

$111

20

Paradise Villa

Central Florida / Winter Garden

Winter Garden house

3 6 3 nights min

  • 3 bedrooms
  • sleeps 6
  • 3 nights min
  • Beach / lakeside relaxation
  • Swimming pool
  • Child Friendly

Price per night from

$77

Price per night from

$77

(1) Excellent 

18

Buckeye Butterfly Villa

Central Florida / Winter Garden

Winter Garden camper van

3 8 3 nights min

  • 3 bedrooms
  • sleeps 8
  • 3 nights min
  • Swimming pool
  • Child Friendly
  • Air conditioning

Price per night from

$144

Responds fast!
avg. 2 hours 14 minutes

Price per night from

$144

(2) Very Good 

8

UK Owned vacation home 10 mins from Disney Gates

Central Florida / Winter Garden

Winter Garden house

3 8 5 nights min

  • 3 bedrooms
  • sleeps 8
  • 5 nights min
  • Child Friendly
  • Air conditioning

Price per night from

$97

Price per night from

$97

10

Liki Tiki Village

Central Florida / Winter Garden

Winter Garden condo

2 6 3 nights min

  • 2 bedrooms
  • sleeps 6
  • 3 nights min
  • Child Friendly

Price per night from

$224

Responds fast!
avg. 3 hours 42 minutes

Price per night from

$224

13

Anne's Palisades Condo

Central Florida / Winter Garden

Winter Garden apartment

3 6 min stay varies

  • 3 bedrooms
  • sleeps 6
  • min stay varies
  • Swimming pool
  • Ask about children
  • Air conditioning

Price per night from

$78

Price per night from

$78

14

Michael's Palisades Condo

Central Florida / Winter Garden

Winter Garden apartment

2 6 min stay varies

  • 2 bedrooms
  • sleeps 6
  • min stay varies
  • Swimming pool
  • Ask about children
  • Air conditioning

Price per night from

$78

Price per night from

$78

(3) Excellent 

25

Orlando holiday home, 10 minutes from Disney, gated community with pools

Central Florida / Winter Garden

Winter Garden house

3 6 7 nights min

  • 3 bedrooms
  • sleeps 6
  • 7 nights min
  • Swimming pool
  • Child Friendly
  • Air conditioning

Price per night from

$82

Responds fast!
avg. 1 hour 34 minutes

Price per night from

$82

Great rentals within 20 miles that match your search

Distance approx 14.58 km from Winter Garden

21

1607 Nectarine Trail

Central Florida / Four Corners

Four Corners house

5 12 7 nights min

  • 5 bedrooms
  • sleeps 12
  • 7 nights min
  • Swimming pool
  • Car not necessary

Price per night from

$241

Responds fast!
avg. 3 hours 50 minutes

Price per night from

$241

Distance approx 19.49 km from Winter Garden

41

Fantastic vacation home near Disney attractions

Central Florida / Kissimmee

Kissimmee townhouse

3 7 1 night min

  • 3 bedrooms
  • sleeps 7
  • 1 night min
  • Swimming pool
  • Child Friendly
  • Air conditioning

Price per night from

$114

Price per night from

$114

Distance approx 16.7 km from Winter Garden

54

EM8605 8 bd Glorious Vacation Home, pond view/heated pool/spa/WiFI

Central Florida / Four Corners

Four Corners house

8 20 min stay varies

  • 8 bedrooms
  • sleeps 20
  • min stay varies
  • Swimming pool
  • Child Friendly
  • Air conditioning

Price per night from

$217

Responds fast!
avg. 3 hours 8 minutes

Price per night from

$217

Distance approx 16.56 km from Winter Garden

(28) Very Good 

44

Located in Emerald Island Resort Beautiful 7 Bed 4.5 Bath Villa Close 2 Disney

Central Florida / Kissimmee

Kissimmee villa

7 16 min stay varies

  • 7 bedrooms
  • sleeps 16
  • min stay varies
  • Swimming pool
  • Ask about children
  • Car not necessary
“Vacation” Property was beautiful. Had some issues with the pool. They were prompt and fixed it. Someone before our visit broke the pool table. We didn’t need it but I thought it was awful to do that to other people’s things. Overall we had a wonderful
…see more

Price per night from

$136

Price per night from

$136

Distance approx 19.63 km from Winter Garden

(2) Excellent 

30

4 bed,pool,15min Disney,Bella Vida,Orlando,Florida

Central Florida / Kissimmee

Kissimmee house

4 8 3 nights min

  • 4 bedrooms
  • sleeps 8
  • 3 nights min
  • Swimming pool
  • Child Friendly
  • Air conditioning

Price per night from

$126

Price per night from

$126

Distance approx 16.21 km from Winter Garden

5

Jose's special

Central Florida / Kissimmee

Kissimmee villa

1 4 7 nights min

  • 1 bedroom
  • sleeps 4
  • 7 nights min
  • Swimming pool
  • Child Friendly
  • Air conditioning

Price per night from

$328

Price per night from

$328

Distance approx 19.27 km from Winter Garden

30

Luxurious Pool Villa Disney area Game/cinema-room

Central Florida / Davenport

Davenport villa

7 16 min stay varies

  • 7 bedrooms
  • sleeps 16
  • min stay varies
  • Swimming pool
  • Child Friendly
  • Air conditioning

Price per night from

$194

Responds fast!
avg. 1 hour 57 minutes

Price per night from

$194

Distance approx 16.5 km from Winter Garden

29

Minions Retreat, Disney are our neighbors. Free 5g WIFI

Central Florida / Kissimmee

Kissimmee condo

2 7 3 nights min

  • 2 bedrooms
  • sleeps 7
  • 3 nights min
  • Child Friendly

Price per night from

$103

Price per night from

$103

Distance approx 17.88 km from Winter Garden

10

The Corner House

Central Florida / Davenport

Davenport house

5 10 min stay varies

  • 5 bedrooms
  • sleeps 10
  • min stay varies
  • Swimming pool
  • Ask about children
  • Air conditioning

Price per night from

$213

Price per night from

$213

Distance approx 13.3 km from Winter Garden

27

Westgate Blue Tree Resort

Central Florida / Orlando

Orlando villa

2 6 7 nights min

  • 2 bedrooms
  • sleeps 6
  • 7 nights min
  • Swimming pool
  • Child Friendly
  • Air conditioning

Price per night from

$284

Price per night from

$284

Distance approx 13.23 km from Winter Garden

23

Grande Villas Resort: 2-Bedrooms, Sleeps 6, Full Kitchen

Central Florida / Orlando

Orlando condo

2 6 7 nights min

  • 2 bedrooms
  • sleeps 6
  • 7 nights min
  • Swimming pool
  • Child Friendly
  • Air conditioning

Price per night from

$193

Price per night from

$193

Distance approx 19.49 km from Winter Garden

9

Private pool townhouse

Florida / Buena Ventura Lakes

Buena Ventura Lakes townhouse

3 6 4 nights min

  • 3 bedrooms
  • sleeps 6
  • 4 nights min
  • Swimming pool
  • Child Friendly
  • Air conditioning

Price per night from

$115

Price per night from

$115

Distance approx 15.56 km from Winter Garden

24

NEW! Modern 4BR Kissimmee Condo w/Community Pool!

Central Florida / Four Corners

Four Corners apartment

4 8 min stay varies

  • 4 bedrooms
  • sleeps 8
  • min stay varies
  • Swimming pool
  • Child Friendly
  • Air conditioning

Price per night from

$126

Responds fast!
avg. 9 minutes

Price per night from

$126

Distance approx 14.21 km from Winter Garden

34

Best-in-Class luxury complex near all three Orlando theme parks. Pools, gym, BBQ

Central Florida / Orlando

Orlando apartment

3 8 2 nights min

  • 3 bedrooms
  • sleeps 8
  • 2 nights min
  • Swimming pool
  • Child Friendly
  • Air conditioning

Price per night from

$161

Price per night from

$161

Distance approx 16.52 km from Winter Garden

31

Emerald Island Resort Villa

Central Florida / Four Corners

Four Corners house

6 12 4 nights min

  • 6 bedrooms
  • sleeps 12
  • 4 nights min
  • Swimming pool
  • Child Friendly
  • Air conditioning

Price per night from

$310

Price per night from

$310

Distance approx 16.51 km from Winter Garden

34

8120 Pomo Drive

Central Florida / Four Corners

Four Corners house

5 12 7 nights min

  • 5 bedrooms
  • sleeps 12
  • 7 nights min
  • Swimming pool
  • Car not necessary

Price per night from

$247

Responds fast!
avg. 3 hours 56 minutes

Price per night from

$247

Distance approx 17.79 km from Winter Garden

75

2143 Tripoli Court

Central Florida / Four Corners

Four Corners house

9 20 7 nights min

  • 9 bedrooms
  • sleeps 20
  • 7 nights min
  • Swimming pool
  • Car not necessary

Price per night from

$802

Price per night from

$802

Distance approx 17.56 km from Winter Garden

26

1 BDRM CONDO STAR ISLAND RESORT & CLUB~ HEATED POOLS, LAKE CECILE, OLD TOWN AREA

Florida / Old Town

Old Town condo

1 4 1 night min

  • 1 bedroom
  • sleeps 4
  • 1 night min
  • Swimming pool
  • Child Friendly
  • Air conditioning

Price per night from

$149

Price per night from

$149

Distance approx 18.44 km from Winter Garden

(5) Excellent 

16

Orlando Villa USA - Indian Ridge - 3 miles to Disney

Kissimmee / Indian Ridge

Kissimmee villa

3 6 7 nights min

  • 3 bedrooms
  • sleeps 6
  • 7 nights min
  • Swimming pool
  • Child Friendly
  • Air conditioning

Price per night from

$141

Price per night from

$141

Distance approx 10.94 km from Winter Garden

(2) Excellent 

64

Beautiful 9BR 6Bth Solara Resort Home with Private Pool, Spa and Gameroom

Central Florida / Orlando

Orlando house

9 16 min stay varies

  • 9 bedrooms
  • sleeps 16
  • min stay varies
  • Swimming pool
  • Child Friendly
  • Air conditioning
“King Joshua's 3rd Birthday” Our group of 13 which was 4 generations had a wonderful time (especially the Joshua the Birthday boy! We had plenty of space throughout the entire house. The kids ranging from 3 to 14 loved their separate area in the lof
…see more

Price per night from

$354

Responds fast!
avg. 49 minutes

Price per night from

$354

Distance approx 15.94 km from Winter Garden Show on Map

(8) Very Good 

Certificate of Excellence

20

Encantada Resort 4 bed 3 Bath

Kissimmee / Encantada Resort

Kissimmee townhouse

4 10 5 nights min

  • 4 bedrooms
  • sleeps 10
  • 5 nights min
  • Child Friendly
  • Air conditioning

Certificate of Excellence

Price per night from

$155

Responds fast!
avg. 1 hour 2 minutes

Price per night from

$155

Distance approx 14.56 km from Winter Garden Show on Map

(21) Very Good 

16

Water view/No Rear Neighbor/New furnitures/Tiles #1180

Central Florida / Four Corners

Four Corners villa

5 12 3 nights min

  • 5 bedrooms
  • sleeps 12
  • 3 nights min
  • Swimming pool
  • Child Friendly
  • Air conditioning

Price per night from

$137

Responds fast!
avg. 3 hours 48 minutes

Price per night from

$137

Distance approx 14.24 km from Winter Garden

(3) Very Good 

30

Grand Opening 8 BR Resort House with Private Pool #844

Central Florida / Four Corners

Four Corners villa

8 18 min stay varies

  • 8 bedrooms
  • sleeps 18
  • min stay varies
  • Swimming pool
  • Child Friendly
  • Air conditioning

Price per night from

$194

Responds fast!
avg. 3 hours 48 minutes

Price per night from

$194

Distance approx 16.46 km from Winter Garden

(7) Very Good 

19

Emerald Island Resort

Kissimmee / Emerald Isle Kissimmee

Kissimmee villa

5 12 min stay varies

  • 5 bedrooms
  • sleeps 12
  • min stay varies
  • Swimming pool
  • Child Friendly
  • Air conditioning

Price per night from

$134

Responds fast!
avg. 3 hours 6 minutes

Price per night from

$134

Distance approx 18.66 km from Winter Garden

(3) Excellent 

41

New Upgraded Luxury Villa w/ Frozen & Star Wars Rooms at Encore!

Central Florida / Kissimmee

Kissimmee house

6 16 min stay varies

  • 6 bedrooms
  • sleeps 16
  • min stay varies
  • Swimming pool
  • Child Friendly
  • Air conditioning

Price per night from

$402

Price per night from

$402

Distance approx 16.67 km from Winter Garden

(3) Excellent 

18

Lovely villa on Emerald Island-4 miles from Disney

Central Florida / Kissimmee

Kissimmee villa

4 8 min stay varies

  • 4 bedrooms
  • sleeps 8
  • min stay varies
  • Swimming pool
  • Child Friendly
  • Air conditioning

Price per night from

$163

Price per night from

$163

Distance approx 10.94 km from Winter Garden

46

Gorgeous 4 bedroom 4 bath Champions Gate Town House with Private Splash Pool

Central Florida / Orlando

Orlando townhouse

4 8 min stay varies

  • 4 bedrooms
  • sleeps 8
  • min stay varies
  • Swimming pool
  • Child Friendly
  • Air conditioning

Price per night from

$147

Responds fast!
avg. 49 minutes

Price per night from

$147