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Holiday Rentals with Pools in The Villages

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    Travellers to The Villages are booking December dates now. Secure your holiday rental today, and have the perfect trip.
    27 Matching Rentals in The VillagesView all 45 rentals
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    3 bedroom Designer home1 / 14
    (6)Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Courtyard Villa in The Villages, Florida1 / 13
    (6)Very good
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    2 bedroom, 2 bath courtyard Villa1 / 7
    (4)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    Book Today -Enjoy Perfect Weather1 / 21
    (2)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    • Washer
    • Grill
    • Internet Access
    • DVD Player
    • Air Conditioning
    • Parking
    • Cable/satellite TV
    • Patio
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 18 April 2018
    This home was beautiful! Everything we needed was available for us to use. The Lanai has two cozy rocking chairs, perfect for my husband and myself to sit down and read and...
    Reviewed 4 January 2018
    This house was in a fantastic location, close to town and shopping. It had everything needed to have a relaxing vacation.
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    About this property
    Location, Location, Location! Our home is just a short walk from Spanish Springs Town Square. The newly updated two bedroom, two bath site built home is in the wonderfully convenient Village of El Cortez. Located close to Mira Mesa and Chula Vista golf courses. Also close to the Chula Vista...
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    32159, The Villages, Florida
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    If you want the best location, consider this. Beautiful courtyard villa.1 / 19
    (1)Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Patio
    • Shared Outdoor Pool (Unheated)
    • Grill
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 5 May 2017
    If you want great access to all the fun entertainment and shops and restaurants in the Lake Sumter Labding/Brownwood sections of The Villages you will love this place. The house...
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    About this property
    This beautiful 3 bedroom, 2 bathroom Courtyard Villa model, located in the lovely Eleanor Villas, sleeps 6 and has been furnished in modern Florida style. Courtyard Villas are a favorite model with Villagers; the enclosed courtyard garden offers premium privacy, whether you choose to lounge in the...
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    32163, The Villages, Florida
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Amenities & Details
    • Grill
    • Wi-Fi
    • Washer
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    • Shared Outdoor Pool (Unheated)
    • Cable/satellite TV
    • Patio
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This delightful Ranch model home has 3 bedrooms, 2 bathrooms, sleeps 6, a large gas grill and a complimentary 2-seat golf cart for the duration of your VIR Vacation. Golf carts are a major form of Villages' transport; you are perfectly positioned for golf cart access to shops, restaurants and the...
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    32162, The Villages, Florida
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Private Garden
    • Air Conditioning
    • Shared Outdoor Pool (Unheated)
    • Parking
    • Wi-Fi
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Luxury 3 bedroom 2300 sq. ft. home. 2 full baths Florida Room Living Room Porch with retractible Sun Awning 2 car Garage Golf Cart Garage Upscale Kitchen Storage room in garage 2 golf carts 4 seater and 2 seater Beds- King - Master, Queen - 2nd bedroom, Full 3rd bedroom, Sofa sleeper, lounge bed in...
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    32162, The Villages, Florida
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Cable/satellite TV
    • Parking
    • Air Conditioning
    • Shared Outdoor Pool (Unheated)
    • Wi-Fi
    • Patio
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Poppy Circle is the popular Jasmine Designer model and offers 3 bedrooms, 2 bathrooms, sleeps 6 and includes a complimentary 4-seater gas golf cart for the duration of your VIR Vacation. Golf carts are The Villages' chosen mode of transport, and your perfect position in the lovely Village of Sabal...
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    32162, The Villages, Florida
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    Whole House - Completely New Inside! PET FRIENDLY - Try Our Sleep Number Bed!1 / 17
    (2)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 5 Quick View
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    • Wi-Fi
    • Private Garden
    • Air Conditioning
    • Shared Outdoor Pool (Unheated)
    • Cable/satellite TV
    • Parking
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 22 October 2017
    You never know when looking at photos just what you will walk into and I'm usually disappointed. However, the Little Blue House did not disappoint. My High Expectations were...
    Reviewed 12 October 2017
    House was very comfortable and clean. Everything we needed was there. Owner was extremely responsive to every question. Had a problem with the combo lock upon arrival but owner...
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    About this property
    Our gem is located in a lovely, quiet neighborhood, one of the first in the Villages so you will be surrounded with mature trees, exquisite plantings & beautiful landscapes. Our home has been completely redone with granite countertops in the kitchen and baths. The refrigerator has an in the door...
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    32159, The Villages, Florida
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 5
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    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    Amenities & Details
    • Patio
    • Cable/satellite TV
    • Wi-Fi
    • Shared Outdoor Pool (Unheated)
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    York Terrace is the very popular 2 bedroom, 2 bathroom Patio Villa model, which comfortably sleeps 4 people; a complimentary 4-seater gas golf cart is included for your use for the duration of your stay and is in the well-located Village of Tall Trees. Golf carts are the favorite Villages' mode of...
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    Location Information
    32162, The Villages, Florida
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Shared Outdoor Pool (Unheated)
    • Air Conditioning
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    • Washer
    • Patio
    • Grill
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Location! Upgraded! Outstanding Forest is the popular Jasmine Designer model and offers 3 bedrooms, 2 bathrooms, sleeps 6, has a gas grill and features a complimentary gas 2-seat golf cart for the duration of your VIR Vacation. Golf carts are The Villages' chosen mode of transport, and your perfect...
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    32162, The Villages, Florida
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Wi-Fi
    • Patio
    • Private Outdoor Pool (Unheated)
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Location is everything and beautiful Buxton Terrace has location, location, location! This lovely 3 bedroom, 2 bathroom Designer model is perfectly positioned in the Village of Winifed, sleeps six and has a complimentary 2-seat gas golf cart included for the duration of your VIR Vacation. Golf...
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    32162, The Villages, Florida
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    Luxury home with the most popular floor plan in the Village of Charlotte.1 / 28
    (1)Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Amenities & Details
    • Cable/satellite TV
    • Wi-Fi
    • Grill
    • Shared Outdoor Pool (Unheated)
    • Patio
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 5 May 2017
    This was a good location to have fun all day and relax at night. The house was very clean and neat, great place for all of the family with plenty of room. There is plenty to do...
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    About this property
    The Villages, Florida has many homes to offer, but few come close to the outstanding location of this property. This 3 bedroom, 2 bathroom Gardenia Designer home sleeps 6, has a complimentary gas golf cart included for the duration of your VIR Vacation, and is in the lovely Village of Charlotte....
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    32163, The Villages, Florida
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    Amenities & Details
    • Patio
    • Wi-Fi
    • Shared Outdoor Pool (Unheated)
    • Cable/satellite TV
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Delwood Way is a tastefully decorated open plan 2 bedroom, 2 bathroom home, sleeping 4 comfortably. This lovely home offers a complimentary golf cart for your convenience; he golf cart is The Villages' preferred mode of transport and the popular Village of Pennecamp is the perfect location for...
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    Location Information
    32162, The Villages, Florida
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Secure Parking
    • Wi-Fi
    • Children's Pool
    • Air Conditioning
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    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    So nice place to share with friends at the golf courses, swimming pool, dancing at the squares every night party . Only for us !! People 55 years and plus !! Looking forward to wellcome you at the Villages All shopping centers and supermarkets church, banks movie theatres very Close too!!...
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    32162, The Villages, Florida
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    One of the most popular homes because of the amazing location. FREE Golf Cart1 / 22
    (1)Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Amenities & Details
    • Cable/satellite TV
    • Patio
    • Washer
    • Wi-Fi
    • Parking
    • Air Conditioning
    • Private Outdoor Pool (Heated)
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 5 May 2017
    The villa was in great shape and very clean. Looking forward to the next visit. Fun place if you like golf and relaxation.
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    About this property
    This popular Courtyard Villa model, in the lovely Sharon Villas in the Village of Gilchrist, has three bedrooms, two bathrooms, sleeps 6, has a complimentary golf cart for the duration of your VIR Vacation Rental and has a high degree of privacy created by the enclosed back garden. The golf cart is...
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    Location Information
    32163, The Villages, Florida
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Air Conditioning
    • Wi-Fi
    • Parking
    • Private Garden
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Look no further! Newest neighborhood in The Villages! 2018 3/2 home. For you and friends (including pets) to call home and build memories that last a lifetime. NEIGHBORHOOD: With amenity passes, you have access to all that is available in The Villages. Over 90 pools, golf, music and dancing every...
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    Location Information
    32163, The Villages, Florida
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Amenities & Details
    • Wi-Fi
    • Air Conditioning
    • Parking
    • Washer
    • Grill
    • Private Outdoor Pool (Heated)
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Perfectly positioned at the end of a Cul-de-Sac in Lake Deaton is this stunning home, which features 3 bedrooms, 2 bathrooms, sleeps 6 and is immaculate. This amazing home has been upgraded to feature an over-sized lanai with a stunning pool. Brownwood Paddock Square, The Villages' newest town...
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    32163, The Villages, Florida
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    2 Bedrooms, 2 Bathrooms, Sleeps 6 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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    32159, The Villages, Florida
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    3 Bedrooms, 3 Bathrooms, Sleeps 2 Quick View
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    • Air Conditioning
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    • Balcony
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    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
    32162, The Villages, Florida
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 2
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    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Wi-Fi
    • Children's Pool
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Way too cold up North…then South you must go! Come to the perfect setting at The Villages in the Center of the sunny state of Florida. Our home has everything you are looking for; a great location to everything, a lanai overlooking a very tranquil view, an electric golf cart to “buzz” around in and...
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    32162, The Villages, Florida
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    • Cable/satellite TV
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    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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    32163, The Villages, Florida
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    DESIRABLE LOCATION WINIFRED VILLAGE DESIGNER HOME1 / 12
    (1)Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 5 Quick View
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    • Cable/satellite TV
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    • Private Garden
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    Pet friendly
    Kid friendly
    Smoking allowed
    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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    32162, The Villages, Florida
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 5
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    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    • Air Conditioning
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Lovely 2 bedroom, 2 bath, fully furnished in excellent condition. Perfectly located in the village of Fernandina, you'll be only a short golf cart (included!) drive away from the Bradenton Village Center, the Gilchrist and Manatee Recreational Centers, and the Bonifay Country Club, among others....
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    32163, The Villages, Florida
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    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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    32162, The Villages, Florida
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • Cable/satellite TV
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    Pet friendly
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    Smoking allowed
    About this property
    Nestled in a quiet cul-de-sac, this charming 3-bedroom, 2-bathroom The Villages vacation rental house is the perfect destination for your relaxing Sunshine State escape. With accommodations for up to 8 guests, this property is perfect for families or groups of friends looking to spend some time...
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    32162, The Villages, Florida
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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    3 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    Smoking allowed
    About this property
    Your vacation in The Villages will be everything you dreamed and more when you stay at this delightful 3-bedroom, 2-bathroom home within the idyllic gated community, The Villages! With room for 6 guests, a tranquil atmosphere with screened patio, a nature walk within the community, and access to a...
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    32163, The Villages, Florida
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 4
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