Crestwynd Bay Rentals

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24,614 Houses

(1) Excellent 

43

Your Great Search Is Over ⁑ Premium Remarkable Home ⁑ Private Outstanding Oasis

Kissimmee / Crestwynd Bay

Kissimmee townhouse

3 7 min stay varies

  • 3 bedrooms
  • sleeps 7
  • min stay varies
  • Nearest beach 97 mi
  • Swimming pool
  • Child Friendly

Price per night from

$55

Price per night from

$55

Great rentals within 20 miles that match your search

Distance approx 4.96 km from Crestwynd Bay

24

NEW! Luxurious 2BR Davenport House - Near Disney!

Central Florida / ChampionsGate

ChampionsGate apartment

2 6 6 nights min

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

Price per night from

$80

Responds fast!
avg. 2 hours 33 minutes

Price per night from

$80

Distance approx 13.55 km from Crestwynd Bay

20

Golf Course View-7 BR-4masters-Pool-Game Room-WiFi

Central Florida / Orlando

Orlando house

7 16 min stay varies

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

Price per night from

$169

Responds fast!
avg. 3 hours 24 minutes

Price per night from

$169

Distance approx 4.21 km from Crestwynd Bay

25

VistaPark 300 5 Bed,7 Bath Large Pool Home with amazing Games Room,Near Disney!

Central Florida / Four Corners

Four Corners house

5 10 min stay varies

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

Price per night from

$150

Price per night from

$150

Distance approx 7.94 km from Crestwynd Bay

24

New! Cozy 4BR Davenport Villa w/Pool & Game Room!

Central Florida / Davenport

Davenport villa

4 8 3 nights min

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

Price per night from

$95

Responds fast!
avg. 10 minutes

Price per night from

$95

Distance approx 4.15 km from Crestwynd Bay

10

Wyndham Bonnet Creek 3 Bedroom Deluxe

Central Florida / Orlando

Orlando villa

3 10 7 nights min

  • 3 bedrooms
  • sleeps 10
  • 7 nights min
  • Swimming pool
  • Child Friendly
  • Air conditioning

Price per night from

$499

Responds fast!
avg. 51 minutes

Price per night from

$499

Distance approx 5.6 km from Crestwynd Bay

(2) Excellent 

36

Luxury Villa with Grill, Private Pool & Spa with Free Pool Heat!

Central Florida / ChampionsGate

ChampionsGate villa

6 14 min stay varies

  • 6 bedrooms
  • sleeps 14
  • min stay varies
  • Nearest beach 123 mi
  • Swimming pool
  • Child Friendly

Price per night from

$275

Responds fast!
avg. 2 hours 2 minutes

Price per night from

$275

Distance approx 3.81 km from Crestwynd Bay

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

$125

Price per night from

$125

Distance approx 1.98 km from Crestwynd Bay

(1) Excellent 

39

Beautiful 8 Bedroom Home with Private Pool at the Encore Club

Central Florida / Reunion

Reunion house

8 18 3 nights min

  • 8 bedrooms
  • sleeps 18
  • 3 nights min
  • Swimming pool
  • Child Friendly
  • Air conditioning

Price per night from

$450

Price per night from

$450

Distance approx 11.33 km from Crestwynd Bay

(2) Excellent 

45

Orlando Best Location 3 Bdroom Townhouse

Central Florida / Orlando

Orlando house

3 8 min stay varies

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

Price per night from

$190

Price per night from

$190

Distance approx 8.1 km from Crestwynd Bay

14

This is a 4/3 Pool Home property, fully furnished, with a full kitchen, and has

Central Florida / Davenport

Davenport house

4 8 min stay varies

  • 4 bedrooms
  • sleeps 8
  • min stay varies
  • Suitable for children age 5+

Price per night from

$197

Price per night from

$197

Distance approx 8.26 km from Crestwynd Bay

6

Fountains Resort

Central Florida / Orlando

Orlando villa

2 6 2 nights min

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

Price per night from

$150

Price per night from

$150

Distance approx 5.32 km from Crestwynd Bay

33

Fresh and Relaxing Home

Central Florida / ChampionsGate

ChampionsGate house

3 6 3 nights min

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

Price per night from

$99

Price per night from

$99

Distance approx 5.11 km from Crestwynd Bay

24

NEW! Family-Friendly 3BR Townhome Near Disney!

Central Florida / Davenport

Davenport house

3 8 3 nights min

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

Price per night from

$89

Responds fast!
avg. 10 minutes

Price per night from

$89

Distance approx 11.24 km from Crestwynd Bay

15

4/3.5 Pool Home located in Victoria Woods at Providence resort community

Central Florida / Davenport

Davenport house

4 8 min stay varies

  • 4 bedrooms
  • sleeps 8
  • min stay varies
  • Suitable for children age 5+

Price per night from

$197

Price per night from

$197

Distance approx 5.84 km from Crestwynd Bay

10

115 Canna Drive

Central Florida / Four Corners

Four Corners villa

6 12 3 nights min

  • 6 bedrooms
  • sleeps 12
  • 3 nights min
  • Swimming pool
  • Ask about children
  • Pet Friendly

Price per night from

$149

Price per night from

$149

Distance approx 14.36 km from Crestwynd Bay

40

NEW for 2018 3-UP SPARK and separate deck overlooking Lake NO EXTRA CLEANING FEE

Lake County / Clermont

Clermont cottage

3 8 1 night min

  • 3 bedrooms
  • sleeps 8
  • 1 night min
  • Nearest beach 0.05 mi
  • Child Friendly
  • Air conditioning

Price per night from

$180

Price per night from

$180

Distance approx 8.05 km from Crestwynd Bay

14

Fun filled Orlando. Stay at the Fountains and be in the middle of everything.

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

$160

Price per night from

$160

Distance approx 6.5 km from Crestwynd Bay

47

Splendid Views on Elqui's House

Central Florida / Davenport

Davenport house

6 15 min stay varies

  • 6 bedrooms
  • sleeps 15
  • min stay varies
  • Swimming pool
  • Child Friendly
  • Air conditioning

Price per night from

$150

Responds fast!
avg. 3 hours 24 minutes

Price per night from

$150

Distance approx 1.05 km from Crestwynd Bay

32

Luxurious family friendly 5 BD house close to Disney, Pool, Spa & Big Theater

Central Florida / Four Corners

Four Corners house

5 10 1 night min

  • 5 bedrooms
  • sleeps 10
  • 1 night min
  • Swimming pool
  • Child Friendly
  • Air conditioning

Price per night from

$165

Price per night from

$165

Distance approx 1.61 km from Crestwynd Bay

(1) Excellent 

38

2CLOSE TO ALL ATTRACTIONS! RESORT LUXURY LIVING ON A BUDGET!

Central Florida / Kissimmee

Kissimmee townhouse

3 12 1 night min

  • 3 bedrooms
  • sleeps 12
  • 1 night min
  • Swimming pool
  • Child Friendly
  • Air conditioning

Price per night from

$249

Price per night from

$249

Distance approx 11.22 km from Crestwynd Bay

30

Amazing Vacation Penthouse In Gorgeous Vista Cay. Next to Convention Center!

Central Florida / Orlando

Orlando condo

3 8 min stay varies

  • 3 bedrooms
  • sleeps 8
  • min stay varies
  • Swimming pool
  • Child Friendly

Price per night from

$169

Price per night from

$169

Distance approx 8.08 km from Crestwynd Bay

15

Envious 4/3 Pool Home in Victoria Woods at Providence Golf and Country Club

Florida / Sand Lake

Sand Lake house

4 8 min stay varies

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

Price per night from

$171

Price per night from

$171

Distance approx 3.76 km from Crestwynd Bay

65

Luxury 9 Bed / 10 Bath Villa in Reunion

Central Florida / Reunion

Reunion villa

9 22 min stay varies

  • 9 bedrooms
  • sleeps 22
  • min stay varies
  • Nearest beach 140 mi
  • Swimming pool
  • Child Friendly

Price per night from

$798

Responds fast!
avg. 15 minutes

Price per night from

$798

Distance approx 11.24 km from Crestwynd Bay

15

Highlands Reserve 4/2 pool home property. Plush furnishings - a perfect home

Central Florida / Davenport

Davenport house

4 8 min stay varies

  • 4 bedrooms
  • sleeps 8
  • min stay varies
  • Suitable for children age 5+

Price per night from

$171

Price per night from

$171

Distance approx 3.37 km from Crestwynd Bay

37

Professionally Decorated, 6 bed 5 bath pool home in Beautiful Paradise Palms

Central Florida / Kissimmee

Kissimmee house

6 12 min stay varies

  • 6 bedrooms
  • sleeps 12
  • min stay varies
  • Child Friendly

Price per night from

$210

Responds fast!
avg. 2 hours 54 minutes

Price per night from

$210

Distance approx 3.44 km from Crestwynd Bay

24

5 Bedroom Villa - Paradise Palms - Private Pool

Central Florida / Four Corners

Four Corners villa

5 12 min stay varies

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

Price per night from

$145

Price per night from

$145

Distance approx 11.41 km from Crestwynd Bay

40

Lake View Penthouse Loft

Central Florida / Orlando

Orlando apartment

3 6 min stay varies

  • 3 bedrooms
  • sleeps 6
  • min stay varies
  • Swimming pool
  • Car not necessary
  • Air conditioning

Price per night from

$216

Responds fast!
avg. 1 hour 40 minutes

Price per night from

$216

Distance approx 2.24 km from Crestwynd Bay

19

5 Bedroom Villa with south facing pool!

Central Florida / Four Corners

Four Corners villa

5 10 3 nights min

  • 5 bedrooms
  • sleeps 10
  • 3 nights min
  • Child Friendly

Price per night from

$185

Price per night from

$185

Distance approx 3.97 km from Crestwynd Bay

33

Amazing House! Bahama Bay - 507RR

Central Florida / Four Corners

Four Corners condo

2 4 min stay varies

  • 2 bedrooms
  • sleeps 4
  • min stay varies
  • Swimming pool
  • Child Friendly
  • Car not necessary

Price per night from

$275

Responds fast!
avg. 1 hour 40 minutes

Price per night from

$275

Distance approx 8.21 km from Crestwynd Bay

26

oasis near of disney world

Florida / Intercession City

Intercession City townhouse

3 7 2 nights min

  • 3 bedrooms
  • sleeps 7
  • 2 nights min
  • Nearest beach 89 mi
  • Swimming pool
  • Child Friendly

Price per night from

$70

Price per night from

$70

Distance approx 6.54 km from Crestwynd Bay

27

3 BDRM~ SLEEPS 8~ STAR ISLAND RESORT~ NEAR OLD TOWN~ ON LAKE CECILE~ HEATED POOL

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

$160

Price per night from

$160

Distance approx 2.19 km from Crestwynd Bay

25

Amazing House! - Emerald Isle - 8555SKD

Central Florida / Four Corners

Four Corners villa

5 10 5 nights min

  • 5 bedrooms
  • sleeps 10
  • 5 nights min
  • Swimming pool
  • Child Friendly
  • Car not necessary

Price per night from

$284

Responds fast!
avg. 1 hour 55 minutes

Price per night from

$284

Distance approx 11.98 km from Crestwynd Bay

21

Lovely 5 bedroom 3 bath home with private pool from $173 a night

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

$173

Responds fast!
avg. 53 minutes

Price per night from

$173

Distance approx 4.13 km from Crestwynd Bay

19

SunSet Lake View

Central Florida / Reunion

Reunion villa

4 10 3 nights min

  • 4 bedrooms
  • sleeps 10
  • 3 nights min
  • Swimming pool
  • Ask about children
  • Air conditioning

Price per night from

$150

Price per night from

$150

Distance approx 5.22 km from Crestwynd Bay

16

Superb Modern Home South West Facing Pool Backing Onto Conservation area

Central Florida / Loughman

Loughman house

5 10 min stay varies

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

Price per night from

$89

Price per night from

$89

Distance approx 11.99 km from Crestwynd Bay

57

Luxury 14BR 11bth Solterra Resort home w/private pool and spa from $523 a night

Central Florida / Orlando

Orlando house

14 28 min stay varies

  • 14 bedrooms
  • sleeps 28
  • min stay varies
  • Swimming pool
  • Child Friendly
  • Air conditioning

Price per night from

$523

Responds fast!
avg. 53 minutes

Price per night from

$523

Distance approx 1.58 km from Crestwynd Bay

16

Gated cozy 3bd villa, Overlook Pool, 3mi to Disney

Central Florida / Four Corners

Four Corners townhouse

3 8 min stay varies

  • 3 bedrooms
  • sleeps 8
  • min stay varies
  • Ask about children
  • Air conditioning

Price per night from

$82

Price per night from

$82