Winter Park vacation rentals

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Handpicked vacation rentals in Winter Park

Downtown Apartments By Nuovo photos Exterior
7.0
Very goodBased onreviews
44
Downtown Apartments By Nuovo Orlando
750 N Orange Ave, Orlando
from US$  96
Thurston House photos Exterior
9.8
PerfectBased onreviews
36
Thurston House Villa Orlando
851 Lake Avenue, Orlando
from US$  201
Beautiful 2 Bed 2 Bath Town Home In Ventura Country Club photos Exterior
13
Beautiful 2 Bed 2 Bath Town Home In Ventura Country Club Orlando
3006 Clubview Drive, Orlando
from US$  190
Sp07L5 Condo photos Exterior
24
Sp07L5 Condo Orlando
, Orlando
from US$  120
Charming Longwood Home With Pool And Theater Room! photos Exterior
36
Charming Longwood Home With Pool And Theater Room! Orlando
Longwood, FL, 32750, Orlando
from US$  265
Reunion Dory 5 Bedrooms Sleeps 10 Encore Club Private Pool photos Exterior
8
Reunion Dory 5 Bedrooms Sleeps 10 Encore Club Private Pool Orlando
201 Pendant Court, Orlando
from US$  444
Villa 2807 Oak Island Harbour Orlando. photos Exterior
4
Villa 2807 Oak Island Harbour Orlando.
2807 Oak Island Harbor, Orlando
Muligan photos Exterior
30
Muligan Villa Orlando
, Orlando
from US$  287
House photos Exterior
3
House Apartment Orlando
Bridgewater Drive, Orlando
from US$  57
Stylish Getaway W/Amazing Pool Deck -5 Mins To Dt! photos Exterior
37
Stylish Getaway W/Amazing Pool Deck -5 Mins To Dt! Villa Orlando
, Orlando
from US$  192

Exclusive luxury places to stay in Winter Park

Majorca Drive photos Exterior
21
Majorca Drive Villa Orlando
, Orlando
from US$  325
Rome Drive photos Exterior
19
Rome Drive Villa Orlando
2078 Rome Drive, Windsor at westside, Orlando
from US$  294
Gatsby Drive photos Exterior
11
Gatsby Drive Villa Orlando
, Orlando
from US$  288
Stunning Orlando Golf Resort 3 Bedroom Vacation Home photos Exterior
29
Stunning Orlando Golf Resort 3 Bedroom Vacation Home
3950 Ventura Place, Orlando
from US$  242
Claremont Three-Bedroom Townhouse #2924 photos Exterior
25
Claremont Three-Bedroom Townhouse #2924 Orlando
, Orlando
from US$  176
Clubview Condo #231699 photos Exterior
9
Clubview Condo #231699 Orlando
, Orlando
from US$  147
The Secret Garden Of Downtown Orlando photos Exterior
20
The Secret Garden Of Downtown Orlando Apartment
1304 Spring Lake Drive, Orlando
from US$  125
Atrium Condo #231707 photos Exterior
13
Atrium Condo #231707 Orlando
4039 Atrium Dr., Orlando
from US$  117
Best Kept Secret Westridge Condo photos Exterior
11
Best Kept Secret Westridge Condo Orlando
3269 Westridge Dr., Orlando
from US$  115
Ventura Country Club Willowpointe Condo photos Exterior
23
Ventura Country Club Willowpointe Condo Orlando
6168 Willowpointe Cir., Orlando
from US$  110

High graded cheap vacation homes in Winter Park

Beautiful 2 Bedroom 2 Bath Condominium photos Exterior
12
Beautiful 2 Bedroom 2 Bath Condominium Orlando
3224 Candle Ridge Dr, Orlando
from US$  109
Altamonte Springs Home W/Canoe On Lake Marion photos Exterior
24
Altamonte Springs Home W/Canoe On Lake Marion Orlando
, Orlando
from US$  71
Charming 2 Bedroom 2 Bath Condo! photos Exterior
17
Charming 2 Bedroom 2 Bath Condo! Orlando
6108 Burnside Cir , Orlando
from US$  69
Golf Course View 2 Bedroom 2 Bath Condo! photos Exterior
11
Golf Course View 2 Bedroom 2 Bath Condo! Orlando
6084 Willowpoint Cir , Orlando
from US$  69
Modern Atrium Drive Condo photos Exterior
10
Modern Atrium Drive Condo Orlando
3942 Atrium Dr, Orlando
from US$  69
Gated Country Club Condominium photos Exterior
16
Gated Country Club Condominium Orlando
3584 Southpointe Dr , Orlando
from US$  69
Serene 2 Bedroom 2 Bath Condo photos Exterior
19
Serene 2 Bedroom 2 Bath Condo Orlando
3905 Atrium Dr, Orlando
from US$  64
Atrium Drive Getaway photos Exterior
15
Atrium Drive Getaway Villa Orlando
3996 Atrium Dr., Orlando
from US$  50
Elegant College Park Cottage With Patio And Gas Grill! photos Exterior
26
Elegant College Park Cottage With Patio And Gas Grill!
, Orlando
Raintree Holiday Home photos Exterior
26
Raintree Holiday Home Orlando
2924 Claremont Ct., Orlando
SHOW ALL 47 VACATION RENTALS IN Winter Park

GUEST REVIEWS

S
Singlefrom United States2020
9.6

Art Deco Suites

F
Family with childrenfrom United States2020
35.0

Holiday Inn Express Malta

F
Family with childrenfrom United States2020
40.0

Ideal Prime Beach

F
Family with childrenfrom United States2020
50.0

Lenox Saint Germain

C
Couplefrom United States2020
9.2

Green Orchid Homestay

A
A.from United States2020
8.0

Chamberlain

F
Family with childrenfrom United States2020
8.8

The Orleans Hotel And Casino

G
Georgefrom United States2020
10.0

Park Avenue J Hotel London Hyde Park

G
Group of friendsfrom United States2020
9.2

Calabogie Motor Inn

G
Group of friendsfrom United States2020
10.0

Summerwind Resort #302