10 Best Winter Haven Apartments on Holiday Lettings - Vacation rentals

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8,558 Vacation rentals

(6) Excellent 

28

Vacation home in Winter Haven

Central Florida / Winter Haven

3 6 1 night min

  • 3 bedrooms
  • sleeps 6
  • 1 night min
  • Child friendly
  • Air conditioning
  • Private garden
Nice and Cozy house next to Legoland. Enjoy this magnificent vacation home that has 3 bedrooms it will comfortably accommodate 6 guests. It has a nice back yard and the house is completely furnished and has everything you need to enjoy your vacations with us. Please …see more

from $79 / night

$498 / week

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from $79 / night

31

Villa rental in Winter Haven

Central Florida / Winter Haven

2 7 min stay varies

  • 2 bedrooms
  • sleeps 7
  • min stay varies
  • Child friendly
  • Air conditioning
Stylish vacation home on Lake Eloise This vacation home is one of seven units located in Cypress Inlet, a new resort community located on Lake Eloise, in Winter Haven, FL. This vacation rental has two bedrooms, two full bathrooms and sleeps up to seven people. It featur …see more

from $120 / night

$840 / week

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Responds fast!
avg. 3 hours 28 minutes

from $120 / night

(3) Very Good 

22

Vacation villa in Winter Haven

Central Florida / Winter Haven

3 6 4 nights min

  • 3 bedrooms
  • sleeps 6
  • 4 nights min
  • Nearest beach 126 mi
  • Swimming pool
  • Child friendly
This beautiful 2615 sq.ft. 3 bedrooms, 2 bathrooms, saltwater pool home, built in 2010, sits in a gated community in the south of Winter Haven, Florida, and features everything you need for a relaxing vacation. The home provides a large fully screened heated saltwater …see more

from $124 / night

$863 - $1,218 / week

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Responds fast!
avg. 3 hours 4 minutes

from $124 / night

24

Villa rental in Winter Haven

Central Florida / Winter Haven

1 4 min stay varies

  • 1 bedroom
  • sleeps 4
  • min stay varies
  • Child friendly
  • Air conditioning
This home is conveniently located near Lake Eloise in Winter Haven next to the Legoland resort. This community has a boat launch with a fully stocked lake. Great for families that want to get away from the hustle and bustle of the busy resorts.This home has one queen be …see more

from $105 / night

$735 / week

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Responds fast!
avg. 3 hours 28 minutes

from $105 / night

(3) Excellent 

20

Vacation home in Winter Haven

Central Florida / Winter Haven

3 10 3 nights min

  • 3 bedrooms
  • sleeps 10
  • 3 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
Our home has a beautiful enclosed salt water pool and is accessible by boat on the chain of lakes. 15 min to Legoland 45 min to Disney or Bush Gardens. One hour to the airports. Three Bedrooms with 2 King master suites (one with walk in shower and Jacuzzi and one with w …see more

from $225 / night

$1,575 / week

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from $225 / night

(2) Good 

12

Vacation home in Winter Haven

Central Florida / Winter Haven

1 3 1 night min

  • 1 bedroom
  • sleeps 3
  • 1 night min
  • Child friendly
  • Air conditioning
  • Ask about pets
Welcome to the Daffodil Cottage! A brand new quaint & charming Tiny Home on beautiful Lake Mariana, located near Legoland, Disney World & Bok Tower Gardens! Come try Tiny Life enjoying included kayaks & canoe, fish, or relax around the fire pit! This is a 160 sq ft tin …see more

from $65 / night

$400 / week

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Responds fast!
avg. 2 hours 49 minutes

from $65 / night

34

Villa rental in Winter Haven

Central Florida / Winter Haven

2 6 min stay varies

  • 2 bedrooms
  • sleeps 6
  • min stay varies
  • Child friendly
  • Air conditioning
This home is conveniently located near Lake Eloise in Winter Haven next to the Legoland resort. This community has a boat launch great for families that want to get away from the hustle and bustle of the busy resorts. This home has one queen bedroom with a partitioned …see more

from $120 / night

$840 / week

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Responds fast!
avg. 3 hours 28 minutes

from $120 / night

28

Villa rental in Winter Haven

Central Florida / Winter Haven

1 4 min stay varies

  • 1 bedroom
  • sleeps 4
  • min stay varies
  • Child friendly
  • Air conditioning
This home is conveniently located near Lake Eloise in Winter Haven next to the Legoland resort. This community has a boat launch with a fully stocked lake. Great for families that want to get away from the hustle and bustle of the busy resorts.This home has one queen be …see more

from $105 / night

$735 / week

Book View

Responds fast!
avg. 3 hours 28 minutes

from $105 / night

29

Villa rental in Winter Haven

Central Florida / Winter Haven

1 4 min stay varies

  • 1 bedroom
  • sleeps 4
  • min stay varies
  • Child friendly
  • Air conditioning
This home is conveniently located near Lake Eloise in Winter Haven next to the Legoland resort. This community has a boat launch with a fully stocked lake. Great for families that want to get away from the hustle and bustle of the busy resorts.This home has one queen be …see more

from $105 / night

$735 / week

Book View

Responds fast!
avg. 3 hours 28 minutes

from $105 / night

10

Vacation home in Winter Haven

Central Florida / Winter Haven

2 5 90 nights min

  • 2 bedrooms
  • sleeps 5
  • 90 nights min
  • Air conditioning
  • Pet friendly
  • Private garden
Spacious lakefront double-wide home available for the 2017//2018 winter. 2 bedrooms, 2 baths, mud room with washer&dryer, den & Florida room, carport and large storage shed. Recently furnished and equipped. Large dining room and kitchen. Swiss Village Community, Winter …see more

from $62 / night

$432 / week

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Responds fast!
avg. 1 hour 34 minutes

from $62 / night

33

Villa rental in Winter Haven

Central Florida / Winter Haven

2 7 min stay varies

  • 2 bedrooms
  • sleeps 7
  • min stay varies
  • Child friendly
  • Air conditioning
This home is conveniently located near Lake Eloise in Winter Haven next to the Legoland resort. This community has a boat launch great for families that want to get away from the hustle and bustle of the busy resorts.This home has two bedrooms. A master bedroom with a k …see more

from $120 / night

$840 / week

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Responds fast!
avg. 3 hours 28 minutes

from $120 / night