Windermere Rentals

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22,514 Houses

25

PARADISE

Central Florida / Windermere

Windermere house

4 10 min stay varies

  • 4 bedrooms
  • sleeps 10
  • min stay varies
  • Swimming pool
  • Ask about children

Price per night from

$1,000

Price per night from

$1,000

7

Deluxe Classy Fun Luxury Private Vacation House

Central Florida / Windermere

Windermere house

5 8 2 nights min

  • 5 bedrooms
  • sleeps 8
  • 2 nights min
  • Nearest beach 115 mi
  • Swimming pool
  • Child Friendly

Price per night from

$287

Responds fast!
avg. 2 hours 2 minutes

Price per night from

$287

31

2901EW

Central Florida / Windermere

Windermere townhouse

4 8 5 nights min

  • 4 bedrooms
  • sleeps 8
  • 5 nights min
  • Swimming pool
  • Ask about children
  • Air conditioning

Price per night from

$129

Price per night from

$129

49

Private Home in the Heart of Orlando!

Central Florida / Windermere

Windermere guest house

2 4 1 night min

  • 2 bedrooms
  • sleeps 4
  • 1 night min

Price per night from

$115

Price per night from

$115

31

2901EW

Central Florida / Windermere

Windermere townhouse

4 8 5 nights min

  • 4 bedrooms
  • sleeps 8
  • 5 nights min
  • Swimming pool
  • Ask about children
  • Air conditioning

Price per night from

$129

Responds fast!
avg. 2 hours 58 minutes

Price per night from

$129

18

Lucaya Village 17 - Modern townhouse with covered porch near Disney

Central Florida / Windermere

Windermere house

4 8 5 nights min

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

Price per night from

$107

Price per night from

$107

16

Suite Fit for a King | Shuttle to Disney World + SeaWorld + Universal

Central Florida / Windermere

Windermere condo

1 4 2 nights min

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

Price per night from

$100

Price per night from

$100

55

8001 Sand Bar Drive

Central Florida / Windermere

Windermere house

4 10 2 nights min

  • 4 bedrooms
  • sleeps 10
  • 2 nights min
  • Swimming pool
  • Child Friendly
  • Air conditioning

Price per night from

$199

Price per night from

$199

16

Spacious + Bright Suite | Shuttle to Disney World + Sea World + More!

Central Florida / Windermere

Windermere condo

1 6 2 nights min

  • 1 bedroom
  • sleeps 6
  • 2 nights min
  • Swimming pool
  • Child Friendly
  • Air conditioning

Price per night from

$109

Price per night from

$109

13

Cinderella's other Castle

Central Florida / Windermere

Windermere house

3 6 2 nights min

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

Price per night from

$403

Price per night from

$403

21

ORLANDO LAKES AND SPA RESORT XMAS GETAWAY December 2018

Central Florida / Windermere

Windermere condo

3 8 6 nights min

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

Price per night from

$259

Responds fast!
avg. 3 hours 52 minutes

Price per night from

$259

15

Shuttle Access to Disney World + Universal Studios | Spacious Suite!

Central Florida / Windermere

Windermere condo

1 4 2 nights min

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

Price per night from

$91

Price per night from

$91

7

Amazing House! - Lucaya Village - 2901EWUNIT14

Central Florida / Windermere

Windermere townhouse

4 8 5 nights min

  • 4 bedrooms
  • sleeps 8
  • 5 nights min
  • Swimming pool
  • Ask about children
  • Air conditioning

Price per night from

$193

Responds fast!
avg. 1 hour 21 minutes

Price per night from

$193

15

Modern + Elegant Suite in a Great Location | Private Furnished Balcony

Central Florida / Windermere

Windermere condo

1 4 2 nights min

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

Price per night from

$166

Price per night from

$166

16

Comfy Suite Close to Universal Orlando | Shuttle to Disney World

Central Florida / Windermere

Windermere condo

2 6 2 nights min

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

Price per night from

$137

Price per night from

$137

13

Shuttle to Popular Orlando Theme Parks | Cozy + Equipped Suite

Central Florida / Windermere

Windermere condo

1 4 2 nights min

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

Price per night from

$118

Price per night from

$118

Great rentals within 20 miles that match your search

Distance approx 17.7 km from Windermere

(1) Excellent 

29

Cool Elegance Villa in ChampionsGate Resort

Central Florida / Davenport

Davenport villa

8 16 min stay varies

  • 8 bedrooms
  • sleeps 16
  • min stay varies
  • Child Friendly

Price per night from

$301

Price per night from

$301

Distance approx 17.11 km from Windermere

17

The House the Mouse would stay in

Central Florida / Davenport

Davenport villa

5 10 7 nights min

  • 5 bedrooms
  • sleeps 10
  • 7 nights min
  • Beach / lakeside relaxation
  • Nearest beach 97 mi
  • Swimming pool

Price per night from

$100

Price per night from

$100

Distance approx 14.37 km from Windermere

46

NEW! Moana's Secret Getaway w/ Pool & Resort Perks

Central Florida / Reunion

Reunion villa

11 22 min stay varies

  • 11 bedrooms
  • sleeps 22
  • min stay varies
  • Swimming pool
  • Child Friendly
  • Air conditioning

Price per night from

$628

Responds fast!
avg. 10 minutes

Price per night from

$628

Distance approx 13.12 km from Windermere

(30) Excellent 

42

The Mouse House Florida, Rental includes a Pool and in Excellent Location

Central Florida / Kissimmee

Kissimmee villa

3 8 5 nights min

  • 3 bedrooms
  • sleeps 8
  • 5 nights min
  • Swimming pool
  • Child Friendly
  • Air conditioning
“Great House, Great Location we all loved it.” The Mouse House is perfectly located at only a short 10 minute drive to Disney resorts and with easy access to road main links to all the other area attractions but is set within a quiet area that is idea
…see more

Price per night from

$112

Responds fast!
avg. 2 hours 24 minutes

Price per night from

$112

Distance approx 9.96 km from Windermere

24

NEW! 3BR Orlando House - 11 Miles to Disney Parks!

Florida Panhandle / Southport

Southport house

3 8 min stay varies

  • 3 bedrooms
  • sleeps 8
  • min stay varies
  • Child Friendly
  • Air conditioning

Price per night from

$126

Responds fast!
avg. 10 minutes

Price per night from

$126

Distance approx 4.95 km from Windermere Show on Map

13

LUXURY Lakes Villa Disney Studio APT

Central Florida / Orlando

Orlando villa

5 7 nights min

  • sleeps 5
  • 7 nights min
  • Beach / lakeside relaxation
  • Swimming pool
  • Child Friendly

Price per night from

$168

Price per night from

$168

Distance approx 12.34 km from Windermere

(3) Very Good 

53

Donald Duck's Condo Unit 305

Central Florida / Kissimmee

Kissimmee apartment

3 6 min stay varies

  • 3 bedrooms
  • sleeps 6
  • min stay varies
  • Swimming pool
  • Child Friendly
  • Air conditioning
“A vacation to be remembered” The service was very friendly and courteous. Checking in was speedy but thorough. The condo was clean, comfortable and adequately furnished. The condo is conveniently located near Disney,Orlando, retail shopping and the be
…see more

Price per night from

$96

Responds fast!
avg. 2 hours 17 minutes

Price per night from

$96

Distance approx 12.82 km from Windermere

39

Lido Palace 2707

Central Florida / Kissimmee

Kissimmee villa

8 20 min stay varies

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

Price per night from

$281

Responds fast!
avg. 42 minutes

Price per night from

$281

Distance approx 9 km from Windermere

(1) Excellent 

6

2BR Luxury Villa next to Disney - Christmas Week

Central Florida / Orlando

Orlando villa

2 8 7 nights min

  • 2 bedrooms
  • sleeps 8
  • 7 nights min
  • Swimming pool
  • Child Friendly
  • Air conditioning
“Awesome facilities, Excellent maintenance and service ..” we liked our stay at the villa very much.. the villa looks exactly the same as shown in the pics .. and the price is much lower than any other villas or hotels offering the same level of servic
…see more

Price per night from

$165

Price per night from

$165

Distance approx 12.37 km from Windermere

50

Unit 21- Crestwynd 7633

Central Florida / Kissimmee

Kissimmee townhouse

3 8 min stay varies

  • 3 bedrooms
  • sleeps 8
  • min stay varies
  • Nearest beach 60 mi
  • Swimming pool
  • Child Friendly

Price per night from

$90

Responds fast!
avg. 52 minutes

Price per night from

$90

Distance approx 14.29 km from Windermere

24

Cottage Grove Townhome #231702

Florida / Ventura

Ventura house

3 6 14 nights min

  • 3 bedrooms
  • sleeps 6
  • 14 nights min
  • Swimming pool
  • Child Friendly
  • Car not necessary

Price per night from

$238

Responds fast!
avg. 2 hours 46 minutes

Price per night from

$238

Distance approx 11.43 km from Windermere

20

Orange Lake Resort Villa, 2br/2ba (Kissimmee)

Central Florida / Orlando

Orlando villa

2 8 4 nights min

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

Price per night from

$151

Price per night from

$151

Distance approx 11.26 km from Windermere

20

4805 Clock Tower Drive

Central Florida / Celebration

Celebration house

4 8 7 nights min

  • 4 bedrooms
  • sleeps 8
  • 7 nights min
  • Swimming pool
  • Car not necessary

Price per night from

$261

Responds fast!
avg. 2 hours 46 minutes

Price per night from

$261

Distance approx 11.75 km from Windermere

23

Regal Resort 4 Bedroom 3 Bathroom Townhouse

Florida / Old Town

Old Town house

4 8 min stay varies

  • 4 bedrooms
  • sleeps 8
  • min stay varies
  • Child Friendly

Price per night from

$107

Responds fast!
avg. 1 hour 26 minutes

Price per night from

$107

Distance approx 11.94 km from Windermere

28

3 BDRM~ SLEEPS 8~ STAR ISLAND RESORT~ HEATED POOLS~ DRIVING RANGE~ PUTTING GREEN

Florida / Old Town

Old Town condo

3 8 1 night min

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

Price per night from

$161

Price per night from

$161

Distance approx 12.38 km from Windermere

55

Unit 24- Seven Dwarfs 2104

Central Florida / Kissimmee

Kissimmee townhouse

3 8 min stay varies

  • 3 bedrooms
  • sleeps 8
  • min stay varies
  • Child Friendly
  • Pet Friendly

Price per night from

$90

Responds fast!
avg. 52 minutes

Price per night from

$90

Distance approx 12.98 km from Windermere

31

8922 Majesty Palm Rd

Central Florida / Four Corners

Four Corners house

4 9 7 nights min

  • 4 bedrooms
  • sleeps 9
  • 7 nights min
  • Swimming pool
  • Car not necessary
  • Air conditioning

Price per night from

$230

Responds fast!
avg. 2 hours 46 minutes

Price per night from

$230

Distance approx 12.98 km from Windermere

(1) Very Good 

24

Amazing 8 Bed in Emerald Island

Central Florida / Kissimmee

Kissimmee house

8 20 min stay varies

  • 8 bedrooms
  • sleeps 20
  • min stay varies
  • Nearest beach 98 mi
  • Child Friendly
“Amazing Get away” Everything was nice and clean just as it is in the pictures kids and family enjoyed our stay will stay again great location close to all restaurants and gas station
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Price per night from

$302

Responds fast!
avg. 2 hours 41 minutes

Price per night from

$302

Distance approx 15.23 km from Windermere

(76) Very Good 

27

Villa Tropico near Disney - FREE cancellation

Central Florida / Davenport

Davenport villa

3 7 4 nights min

  • 3 bedrooms
  • sleeps 7
  • 4 nights min
  • Ask about children
  • Air conditioning

Price per night from

$120

Price per night from

$120

Distance approx 12.85 km from Windermere

(15) Excellent 

30

Paradise on Ice, a FROZEN retreat at Paradise Palms Resort near Disney World

Central Florida / Four Corners

Four Corners townhouse

4 10 min stay varies

  • 4 bedrooms
  • sleeps 10
  • min stay varies
  • Nearest beach 60 mi
  • Swimming pool
  • Child Friendly
“A complete package” It was a complete package, great layout, very clean, nice decor, very clean, fully equipped, very clean, amazing customer service, very clean, owner reachable and did I said very clean. For my family it would be our perfect place t
…see more

Price per night from

$160

Responds fast!
avg. 1 hour 22 minutes

Price per night from

$160

Distance approx 5.39 km from Windermere Show on Map

21

Lovely 5 bedroom 3 bath Highlands Reserve home 7 miles to Disney from $158nt

Central Florida / Orlando

Orlando house

5 10 min stay varies

  • 5 bedrooms
  • sleeps 10
  • min stay varies
  • Swimming pool
  • Child Friendly
  • Air conditioning

Price per night from

$179

Responds fast!
avg. 51 minutes

Price per night from

$179

Distance approx 12.77 km from Windermere

40

BRAND NEW Luxury 6bd Villa Pool No Rear Neighbor Game Room Wifi

Central Florida / Four Corners

Four Corners villa

6 12 3 nights min

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

Price per night from

$250

Responds fast!
avg. 50 minutes

Price per night from

$250