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Winter Haven Vacation Rentals
1-24 of 300+ rentals

The Luxury Lakehouse

$247 avg / night (excludes fees and taxes)
Winter Haven, FL
4.59 (17)
3 Bedrooms | 3 Bath | Sleeps 7

Enchanted Retreat

$176 avg / night (excludes fees and taxes)
NEW!
Haines City, FL
5.0 (2)
4 Bedrooms | 3 Bath | Sleeps 10

The Par-fect Getaway

$136 avg / night (excludes fees and taxes)
Haines City, FL
4.43 (21)
3 Bedrooms | 2 Bath | Sleeps 6

Tower Lake Hideaway

$159 avg / night (excludes fees and taxes)
Haines City, FL
4.45 (22)
4 Bedrooms | 3 Bath | Sleeps 8

Blue Sweet Haven

$161 avg / night (excludes fees and taxes)
Haines City, FL
5.0 (10)
4 Bedrooms | 3 Bath | Sleeps 8

Magic in Haines

$262 avg / night (excludes fees and taxes)
Haines City, FL
4.4 (5)
4 Bedrooms | 3 Bath | Sleeps 8

The Oakmoss Haven

$208 avg / night (excludes fees and taxes)
NEW!
Davenport, FL
5.0 (1)
5 Bedrooms | 4.5 Bath | Sleeps 12

SunDrop Sanctuary

$111 avg / night (excludes fees and taxes)
NEW!
Davenport, FL
2 Bedrooms | 2 Bath | Sleeps 6

Windsor Island Wonder

$211 avg / night (excludes fees and taxes)
Davenport, FL
4.65 (37)
5 Bedrooms | 4.5 Bath | Sleeps 12

Bahama Bay Resort 24207

$142 avg / night (excludes fees and taxes)
Davenport, FL
4.43 (7)
3 Bedrooms | 2 Bath | Sleeps 6

Bahama Bay Resort 33503

$144 avg / night (excludes fees and taxes)
Davenport, FL
4.65 (20)
3 Bedrooms | 2 Bath | Sleeps 6

Bahama Bay Resort 23101

$148 avg / night (excludes fees and taxes)
NEW!
Davenport, FL
2 Bedrooms | 2 Bath | Sleeps 6

Gathering Under the Palms

$90 avg / night (excludes fees and taxes)
Davenport, FL
4.29 (17)
3 Bedrooms | 3 Bath | Sleeps 9

Kindred House

$233 avg / night (excludes fees and taxes)
NEW!
Davenport, FL
5 Bedrooms | 3.5 Bath | Sleeps 10

Bahama Bay Resort 29602

$125 avg / night (excludes fees and taxes)
Davenport, FL
3.0 (11)
3 Bedrooms | 2 Bath | Sleeps 8

Davenport Darling in Windsor Island

$293 avg / night (excludes fees and taxes)
Davenport, FL
4.86 (59)
6 Bedrooms | 4.5 Bath | Sleeps 12

Sunny Haven Retreat

$191 avg / night (excludes fees and taxes)
NEW!
Davenport, FL
4.0 (2)
5 Bedrooms | 4.5 Bath | Sleeps 15

Once Upon a Stay

$402 avg / night (excludes fees and taxes)
NEW!
Davenport, FL
4.0 (1)
8 Bedrooms | 4.5 Bath | Sleeps 18

Artist's Escape - Champions Gate

$229 avg / night (excludes fees and taxes)
Davenport, FL
4.51 (65)
5 Bedrooms | 5 Bath | Sleeps 15

The Magic Castle

$404 avg / night (excludes fees and taxes)
Davenport, FL
4.93 (59)
7 Bedrooms | 5.5 Bath | Sleeps 19

Enchanted Villa - 8 Miles from Disney

$207 avg / night (excludes fees and taxes)
Davenport, FL
4.82 (11)
5 Bed | 4.5 Bath | Sleeps 15 (11 Adults Max)

Roseville Getaway - The Fountains at Champions Gate

$119 avg / night (excludes fees and taxes)
Davenport, FL
4.3 (10)
3 Bedrooms | 2.5 Bath | Sleeps 6

Kaipo Kastle

$587 avg / night (excludes fees and taxes)
Davenport, FL
4.94 (68)
10 Bed | 8 Bath | Sleeps 28 (26 Adults Max)

5BD Davenport Spacious Family Retreat

$151 avg / night (excludes fees and taxes)
Davenport, FL
4.0 (24)
5 Bedrooms | 3 Bath | Sleeps 12
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