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Holiday Rentals with Pools in The Villages

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    Travellers to The Villages are booking February dates now. Secure your holiday rental today, and have the perfect trip.
    14 Matching Rentals in The VillagesView all 29 rentals
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    Book Today -Enjoy Perfect Weather1 / 21
    (2)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    3 Bedrooms, 3 Bathrooms, Sleeps 2 Quick View
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    • Air Conditioning
    • Washer
    • Wi-Fi
    • DVD Player
    • Cable/satellite TV
    • Grill
    • Balcony
    • Parking
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This beautiful newly furnished 3 br home is located 2 minutes from the seabreeze pool, miona rec. Center, cane gardens country club. Just a 5 minute golf cart ride to lake sumpter landing and 10 minutes to the new brownwood village. The spacious master bedroom has a king size bed with 55 inch tv ....
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    Location Information
    The Villages, Central Florida 32162
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 2
    2 Bedrooms, 2 Bathrooms, Sleeps 5 Quick View
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    • Wi-Fi
    • Cable/satellite TV
    • Patio
    • Children's Pool
    • Hot Tub
    • Air Conditioning
    • Washer
    • Housekeeping Included
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Welcome to Tee Off Villa...Our Home of Golf Come and enjoy this beautiful Courtyard Villa. Step through the Florida room to your GIANT lanai under screen enclosure where enjoying the days and evenings will be a highlight. There's a spa/hot tub, plenty of room for hosting friends and family, lots...
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    The Villages, Central Florida 32159
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 5
    DESIRABLE LOCATION WINIFRED VILLAGE DESIGNER HOME1 / 13
    (2)Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 5 Quick View
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    • Cable/satellite TV
    • DVD Player
    • Private Garden
    • Parking
    • Wi-Fi
    • Air Conditioning
    • Patio
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 6 November 2018
    perfect location for everything in the villages,accomodation was excellent.Why would you take 100 characters when you can say it in 75.
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    About this property
    DESIRABLE WINIFRED VILLAGE - Well appointed designer home very close to Sumter Landing! *Golf Cart Included w/roadside assistance *His & Hers cruiser bikes for your riding enjoyment *5 minute cart ride to Sumter Landing shopping, restaurants and entertainment and 3 recreation centers....
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    The Villages, Central Florida 32162
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 5
    True Golf and Sunset Views Stunning. Luxury Living1 / 29
    (3)Very good
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    • Hot Tub
    • Washer
    • Air Conditioning
    • Patio
    • Shared Outdoor Pool (Unheated)
    • DVD Player
    • Wi-Fi
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Professionally decorated & completely furnished Carriage townhome with king size beds in each bedroom. French doors that open to private patio with wonderful golf/sunset views - a fabulous setting to enjoy evening cocktails and morning coffee. Tree lined Glenview Rd. leads to the property and...
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    Location Information
    The Villages, Central Florida 32162
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 4
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Cable/satellite TV
    • DVD Player
    • Wi-Fi
    • Washer
    • Air Conditioning
    • Patio
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    You’re sure to have an amazing getaway when you stay at this 3-bedroom, 2-bathroom vacation rental cottage in The Villages, which sleeps 6. Boasting 1,438 square feet, this property is perfect to travel to with other couples, family or grandchildren. For a small additional fee, enjoy access to...
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    Location Information
    The Villages, Central Florida 32163
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    Amenities & Details
    • Children's Pool
    • Air Conditioning
    • Wi-Fi
    • Private Garden
    • Parking
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Our home has an open and inviting floor plan. Particularly if you are entertaining, you are always within ear and eye shot of your guests. The home is done in large neutral hardwood floor, new paint, and the Master Bedroom has a king bed. It has a beautiful large open kitchen with lots of...
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    Location Information
    The Villages, Central Florida 32163
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 4
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Amenities & Details
    • Wi-Fi
    • DVD Player
    • Air Conditioning
    • Secure Parking
    • Cable/satellite TV
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Village of Caroline This is an absolutely ideal situation for anyone contemplating owning a rental unit in The Villages! Fully furnished turnkey ranch in one of the most sought after locations! Home located within walking distance to the Recreation Center and two pools. Only 1 mile from...
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    Location Information
    The Villages, Central Florida 32162
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    • Cable/satellite TV
    • Grill
    • Wi-Fi
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    For the snowbirds, golfers, and shoppers out there, this 2-bedroom, 2-bathroom vacation rental house in The Villages Florida is the perfect place to call home during your visit to the Sunshine State. Spend your days utilizing the community amenities and your evenings relaxing on the patio grilling...
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    Location Information
    The Villages, Central Florida 32162
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 4
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Washer
    • Wi-Fi
    • Air Conditioning
    • Patio
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Soak up the best of the Sunshine State at this vacation rental! This 3-bed, 2-bath villa will feel like something out of a Florida portrait - framed by a white picket fence, swaying palm trees, and a yard overlooking the fairways. Stay close to home and enjoy on-site amenities—including a private...
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    Location Information
    The Villages, Central Florida 32162
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Wi-Fi
    • Washer
    • Air Conditioning
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Nothing beats a day spent lounging in the sun, sipping a glass of iced tea, and that is what you'll experience when you stay at this vacation rental home in The Villages! The fully-furnished, 3-bed, 2-bath property is located on a quiet cul-de-sac in an active senior resident community with great...
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    Location Information
    The Villages, Central Florida 32162
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
    other travellers have booked this property
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    Amenities & Details
    • Hot Tub
    • Washer
    • DVD Player
    • Wi-Fi
    • Patio
    • Cable/satellite TV
    • Air Conditioning
    • Private Outdoor Pool (Unheated)
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Calling all golf and sunshine lovers! Find paradise in this 3-bedroom, 3-bath vacation rental home for 6 in The Villages of Largo. Sip coffee on the open lanai before enjoying the hot tub or swimming in the private pool complete with a waterfall. This 55+ community offers complimentary activities,...
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    Location Information
    The Villages, Central Florida 32162
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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