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Vacation Rentals near Cypresswood Golf & Country Club

1099 Clubhouse Rd, Winter Haven, Florida 33884-1200
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    Travelers to Winter Haven are booking June dates now. Secure your vacation rental today, and have the perfect trip.
    All 24 Rentals in Winter Haven
    4.4 miles from Cypresswood Golf & Country Club
    3 Bedrooms, 2 Bathrooms, Sleeps 9 Quick View
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    Lake Rochelle Rental (Lakefront)1 / 29
    (35)Excellent
    5.8 miles from Cypresswood Golf & Country Club
    3 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    FALL/WINTER SPECIAL RATES Mid-century Mod w/ Fireplaces - Downtown Near Legoland1 / 26
    (71)Very good
    5.4 miles from Cypresswood Golf & Country Club
    2 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    *3/2*GorgeousNEWLakeHome2AceLoc*4mi*LEGOLAND*17241 / 25
    (35)Excellent
    3.2 miles from Cypresswood Golf & Country Club
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Winter Haven, Central Florida
    Rental Home - 3 Bedrooms, 2 Bathrooms, Sleeps 6
    Charming Home 5 Minutes From Legoland1 / 17
    (18)Excellent
    1.8 miles from Cypresswood Golf & Country Club
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Winter Haven, Central Florida
    Rental Home - 2 Bedrooms, 2 Bathrooms, Sleeps 6
    Are you ready to get back to Living?  This is a GREAT place to start. Come!1 / 24
    (80)Excellent
    3.8 miles from Cypresswood Golf & Country Club
    5 Bedrooms, 5 Bathrooms, Sleeps 12 Quick View
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    • Sauna
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    Winter Haven, Central Florida
    Rental Home - 5 Bedrooms, 5 Bathrooms, Sleeps 12
    Fantastic Water Front Home on the Chain of Lakes1 / 67
    (8)Excellent
    6.7 miles from Cypresswood Golf & Country Club
    4 Bedrooms, 3 Bathrooms, Sleeps 10 Quick View
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    Winter Haven, Central Florida
    Rental Home - 4 Bedrooms, 3 Bathrooms, Sleeps 10
    Winter Haven, FL Pet Friendly Residential Retreat1 / 44
    (16)Excellent
    8.8 miles from Cypresswood Golf & Country Club
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    Winter Haven, Central Florida
    Rental Home - 3 Bedrooms, 2 Bathrooms, Sleeps 8
    Beautiful Lake Front home with pool:30 min  from Disney and Universal Studios.1 / 27
    (12)Excellent
    3.2 miles from Cypresswood Golf & Country Club
    4 Bedrooms, 3 Bathrooms, Sleeps 10 Quick View
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    Winter Haven, Central Florida
    Rental Home - 4 Bedrooms, 3 Bathrooms, Sleeps 10
    3.2 miles from Cypresswood Golf & Country Club
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    Winter Haven, Central Florida
    Rental Home - 1 Bedroom, 1 Bathroom, Sleeps 4
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    2.2 miles from Cypresswood Golf & Country Club
    3 Bedrooms, 1 Bathroom, Sleeps 9 Quick View
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    About this property
    Welcome to Winter Haven! Pack up the SUV and bring the family for a fun weekend away! This centrally located 3 bedroom, 1 bath home that sleeps 9 will be perfect for a big family or two who want to spend time at Legoland or the newly opened Peppa Pig Theme Parks! Just a short 2 mile ride to get...
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    Winter Haven, Central Florida
    Rental Home - 3 Bedrooms, 1 Bathroom, Sleeps 9
    5.1 miles from Cypresswood Golf & Country Club
    4 Bedrooms, 2 Bathrooms, Sleeps 10 Quick View
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    Winter Haven, Central Florida
    Rental Home - 4 Bedrooms, 2 Bathrooms, Sleeps 10
    3.1 miles from Cypresswood Golf & Country Club
    4 Bedrooms, 2 Bathrooms, Sleeps 10 Quick View
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    Location Information
    Winter Haven, Central Florida
    Rental Home - 4 Bedrooms, 2 Bathrooms, Sleeps 10
    Conveniently located 10 minutes from Legoland!1 / 28
    (24)Excellent
    4.4 miles from Cypresswood Golf & Country Club
    3 Bedrooms, 2 Bathrooms, Sleeps 9 Quick View
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    Winter Haven, Central Florida
    Rental Home - 3 Bedrooms, 2 Bathrooms, Sleeps 9
    4.9 miles from Cypresswood Golf & Country Club
    5 Bedrooms, 2 Bathrooms, Sleeps 11 Quick View
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    Winter Haven, Central Florida
    Rental Home - 5 Bedrooms, 2 Bathrooms, Sleeps 11
    College Students! Off Campus Life!1 / 15
    (3)Excellent
    2.2 miles from Cypresswood Golf & Country Club
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    Winter Haven, Central Florida
    Rental Home - 3 Bedrooms, 2 Bathrooms, Sleeps 8
    6.4 miles from Cypresswood Golf & Country Club
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    Winter Haven, Central Florida
    Rental Home - 1 Bedroom, 1 Bathroom, Sleeps 4
    Winter Haven Home with Dock & Hot Tub!1 / 41
    (38)Excellent
    4.5 miles from Cypresswood Golf & Country Club
    4 Bedrooms, 3 Bathrooms, Sleeps 12 Quick View
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    Winter Haven, Central Florida
    Rental Home - 4 Bedrooms, 3 Bathrooms, Sleeps 12
    3.1 miles from Cypresswood Golf & Country Club
    4 Bedrooms, 2 Bathrooms, Sleeps 10 Quick View
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    Location Information
    Winter Haven, Central Florida
    Rental Home - 4 Bedrooms, 2 Bathrooms, Sleeps 10
    Spectacular Waterfront Home in Winter Haven1 / 50
    (22)Excellent
    3.7 miles from Cypresswood Golf & Country Club
    4 Bedrooms, 4 Bathrooms, Sleeps 10 Quick View
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    • Air Conditioning
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    • Balcony
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    Winter Haven, Central Florida
    Rental Home - 4 Bedrooms, 4 Bathrooms, Sleeps 10
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    Newly updated 3/ 2 kid friendly, only minutes to Legoland.1 / 27
    (19)Excellent
    2.8 miles from Cypresswood Golf & Country Club
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    Location Information
    Winter Haven, Central Florida
    Rental Home - 3 Bedrooms, 2 Bathrooms, Sleeps 8
    *3/2*GorgeousNEWLakeHome2AceLoc*4mi*LEGOLAND*17221 / 20
    (27)Excellent
    3.2 miles from Cypresswood Golf & Country Club
    3 Bedrooms, 2 Bathrooms, Sleeps 7 Quick View
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    Location Information
    Winter Haven, Central Florida
    Rental Home - 3 Bedrooms, 2 Bathrooms, Sleeps 7
    Just Bring Your Toothbrush1 / 7
    (4)Very good
    4.0 miles from Cypresswood Golf & Country Club
    3 Bedrooms, 2 Bathrooms, Sleeps 7 Quick View
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    About this property
    Lake Ashton is a premier active adult community. The house offers all that is needed for a comfortable stay. Great golf and many amenities. Amenities include: 26,000 sq ft Clubhouse Full dining/lounge facilities Grand ballroom On-site courses Four-lane bowling center...
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    Location Information
    Lake Wales, Central Florida
    Rental Home - 3 Bedrooms, 2 Bathrooms, Sleeps 7
    1.6 miles from Cypresswood Golf & Country Club
    6 Bedrooms, 4 Bathrooms, Sleeps 13 Quick View
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    • Waterfront
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    Pet friendly
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    Smoking allowed
    About this property
    Come to Lake Hamilton’s luxurious lake house and let the sunsets take your breath away as you relax and enjoy making memories at our gorgeous Mediterranean home! No detail has been missed with gorgeous travertine tile and crown moulding throughout the home. The kitchen is full of natural light...
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    Location Information
    Lake Hamilton, Central Florida
    Rental Home - 6 Bedrooms, 4 Bathrooms, Sleeps 13
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