30 Best The Villages Apartments on Holiday Lettings - Vacation rentals

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71 Vacation rentals

17

Vacation home rental

Florida / The Villages

2 4 30 nights min

  • 2 bedrooms
  • Sleeps 4
  • 30 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
location location location 1/2 mile to Spanish Village Square 1/3 mile to family pool 1/3 mile to adult pool, golf, tennis, rec center and more 2.5 miles to Sumter Landing Village This 2/2 ranch home is completely remolded and furnished, included fully stocked …see more

from $69 / night

$483 / week

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from $69 / night

(1) Excellent 

21

Home accommodation in The Villages with golf nearby

Florida / The Villages

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
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 clo …see more

from $108 / night

$750 - $800 / week

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from $108 / night

(2) Excellent 

24

Vacation home in The Villages

Florida / The Villages

2 5 Min stay varies

  • 2 bedrooms
  • Sleeps 5
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
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 ref …see more

from $55 / night

$750 / week

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Responds fast!
avg. 1 hour 28 minutes

from $55 / night

(3) Excellent 

9

Vacation home in The Villages

Florida / The Villages

1 2 1 night min

  • 1 bedroom
  • Sleeps 2
  • 1 night min
  • Nearest beach 130 mi
  • Air conditioning
We are a B&B and have 2 bedrooms available, each must be reserved separately. The bathroom is private IF THE OTHER ROOM IS NOT OCCUPIED. We are located in the middle of the Villages. We have over 70 swimming pools, 56 golf courses, about 35 recreation centers, tennis co …see more

from $45 / night

$300 / week

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Responds fast!
avg. 2 hours 57 minutes

from $45 / night

(1) Very Good 

8

Vacation villa rental

Florida / The Villages

2 4 7 nights min

  • 2 bedrooms
  • Sleeps 4
  • 7 nights min
  • Air conditioning
This super cute 2 bedroom, 2 bath, patio villa includes all the furnishings, linens and dishes. Conveniently located in the heart of the Villages at Village Rio Ponderosa -just a 5-6 minute drive from either square (Lake Sumter Landing or Spanish Springs). It has a nice …see more

from $43 / night

$300 - $900 / week

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from $43 / night

(6) Excellent 

14

Vacation home with shared pool, golf nearby in The Villages

Florida / The Villages

3 6 5 nights min

  • 3 bedrooms
  • Sleeps 6
  • 5 nights min
  • Beach/lakeside relaxation
  • Nearest beach 40 mi
  • Swimming pool
Vacation house in the Villages, Fl. the # 1 vacation place in the world. Go everywhere by golf cart. Golf, tennis, Pickleball, swimming, softball, volleyball, 600 holes of golf, entertainment nightly on 3 town squares, This is a gated community that is completely s …see more

from $69 / night

$425 - $639 / week

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from $69 / night

(2) Excellent 

32

Vacation home in The Villages

Florida / The Villages

2 4 7 nights min

  • 2 bedrooms
  • Sleeps 4
  • 7 nights min
  • Car not necessary
  • Air conditioning
  • Private garden
This is just the Perfect Patio Villa with stunning, enhanced landscaping a. Our home is super clean and in Pristine condition. Inside the spacious Open Floor Plan, the neutral colors are so inviting that entertaining family and friends will be at the top of your list. …see more

from $99 / night

$693 - $1,043 / week

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from $99 / night

(3) Excellent 

7

The Villages Vacation home rental

Florida / The Villages

2 4 5 nights min

  • 2 bedrooms
  • Sleeps 4
  • 5 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
Gated community, 100% safe. It has over 600 holes of golf, tennis, pools, basketball, you name it, it's here. Across the street from large rec center. Travel everywhere by furnished golf cart. Over 2000 clubs to fit your desires. Home is fenced in. Senior community, bu …see more

from $59 / night

$399 - $595 / week

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Responds fast!
avg. 2 hours 33 minutes

from $59 / night

(4) Excellent 

13

The Villages Vacation home accommodation

Florida / The Villages

2 4 3 nights min

  • 2 bedrooms
  • Sleeps 4
  • 3 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
This is a furnished home in a large adult community of The Villages, Florida. It is located about an hour north of Orlando and both coastlines The town has over 60 pools, many recreation centers with activities,and 12 country clubs with champion courses and 33 exe …see more

from $120 / night

$700 / week

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from $120 / night

(4) Excellent 

13

The Villages Vacation home rental

Florida / The Villages

2 4 5 nights min

  • 2 bedrooms
  • Sleeps 4
  • 5 nights min
  • Child friendly
  • Air conditioning
  • Private garden
It is in a retirement village, but open to all ages. It has over 600 holes of golf, tennis, pickleball, 70 pools, softball, and hundreds of other activities. Golf cart available to use. Car not needed, you can travel everywhere by cart. Free entertainment nightly in 3 t …see more

from $69 / night

$450 - $550 / week

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from $69 / night

11

Vacation b&b in The Villages

Florida / The Villages

1 2 1 night min

  • 1 bedroom
  • Sleeps 2
  • 1 night min
  • Nearest beach 123 mi
  • Air conditioning
  • Private garden
We are a B&B and have 2 bedrooms available, each must be reserved separately. The bathroom is private IF THE OTHER ROOM IS NOT OCCUPIED. We are located in the middle of The Villages. We have over 70 swimming pools, 56 golf courses, about 35 recreation centers, tennis co …see more

from $45 / night

$300 / week

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Responds fast!
avg. 2 hours 57 minutes

from $45 / night

(2) Excellent 

29

The Villages Vacation home rental

Florida / The Villages

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Nearest beach 113 mi
  • Swimming pool
  • Child friendly
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. …see more

from $125 / night

$600 - $990 / week

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Responds fast!
avg. 55 minutes

from $125 / night

(63) Excellent 

11

The Villages Vacation b&b rental

Florida / The Villages

1 2 3 nights min

  • 1 bedroom
  • Sleeps 2
  • 3 nights min
  • Air conditioning
You will LOVE our Luxury Suite! It is on the main level - no stairs at all - great for those that have trouble negotiating stairs! This 3-room suite has comfortable, plush Stearns and Fosters Queen-size mattress set, complete with luxury sheets and non-allergenic pillo …see more

from $300 / night

$2,100 / week

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Responds fast!
avg. 2 hours 47 minutes

from $300 / night

23

Vacation home in The Villages

Florida / The Villages

3 2 30 nights min

  • 3 bedrooms
  • Sleeps 2
  • 30 nights min
  • Nearest beach 112 mi
  • Swimming pool
  • Ask about children
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 ha …see more

from $143 / night

$1,000 / week

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from $143 / night

9

Vacation home in The Villages

Florida / The Villages

3 10 3 nights min

  • 3 bedrooms
  • Sleeps 10
  • 3 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
My Home is perfect for two golfing couples, a family reunion, or a special romantic retreat ! Truly a unique home that is absolutely lovely. You would LOVE my home. I promise. There is a fireplace in the Great Room and Two big tables. One seats 10 to12...the other 6-8. …see more

from $200 / night

$1,200 / week

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from $200 / night

(1)  

24

Vacation home rental

Florida / The Villages

3 4 Min stay varies

  • 3 bedrooms
  • Sleeps 4
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
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 th …see more

from $99 / night

$594 - $1,200 / week

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Responds fast!
avg. 22 minutes

from $99 / night

17

Vacation home rental

Florida / The Villages

3 6 14 nights min

  • 3 bedrooms
  • Sleeps 6
  • 14 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
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 …see more

from $90 / night

$600 - $925 / week

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from $90 / night

24

Vacation cottage with shared pool in The Villages

Florida / The Villages

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
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 additio …see more

from $95 / night

$665 - $1,295 / week

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Responds fast!
avg. 17 minutes

from $95 / night

22

Vacation home in The Villages

Florida / The Villages

3 6 30 nights min

  • 3 bedrooms
  • Sleeps 6
  • 30 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
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 movi …see more

from $150 / night

$1,200 / week

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from $150 / night

14

Vacation home rental

Florida / The Villages

3 6 3 nights min

  • 3 bedrooms
  • Sleeps 6
  • 3 nights min
  • Child friendly
LOCATION! Centrally located and near everything! Walk to Lake Sumter Landing. Designer upgraded home with open concept. This winter having ALL new furniture being bought! Washer and dryer, 2 car garage, privacy patio with paver bricks, climate controlled lanai expanded …see more

from $135 / night

$1,200 / week

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from $135 / night

24

Vacation home with shared pool in The Villages

Florida / The Villages

3 8 Min stay varies

  • 3 bedrooms
  • Sleeps 8
  • Min stay varies
  • Swimming pool
  • Suitable for children age 5+
  • Air conditioning
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 l …see more

from $65 / night

$455 - $840 / week

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Responds fast!
avg. 17 minutes

from $65 / night

4

The Villages Vacation home rental

Florida / The Villages

3 8 90 nights min

  • 3 bedrooms
  • Sleeps 8
  • 90 nights min
  • Child friendly
Location, Location, Location! This Expanded Bougainvillea Designer Home is situated directly on the Kenya Golf Course of the Havana Country Club. Enjoy the wonderful Village of Hemingway. Close to Lake Sumter Landing, Hemingway's Country Club, Havana Golf Course and sho …see more

from $64 / night

$444 / week

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from $64 / night

8

Vacation villa in The Villages

Florida / The Villages

2 3 7 nights min

  • 2 bedrooms
  • Sleeps 3
  • 7 nights min
  • Child friendly
  • Air conditioning
  • Private garden
The Villages Florida Golf course home site This 2 bedroom 2 full baths , courtyard villa is located near the Spanish Springs town square ,entertainment ,recreation and shopping central .New kitchen ,huge private screened lanai ,on the Chula Vista golf course .Club house …see more

from $86 / night

$600 - $700 / week

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Responds fast!
avg. 1 hour 37 minutes

from $86 / night

10

Vacation home in The Villages

Florida / The Villages

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Swimming pool
  • Air conditioning
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 C …see more

from $62 / night

$427 - $896 / week

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from $62 / night

5

Vacation villa in The Villages

Florida / The Villages

2 6 30 nights min

  • 2 bedrooms
  • Sleeps 6
  • 30 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
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 pool …see more

from $120 / night

$840 / week

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from $120 / night

22

Vacation home in The Villages

Florida / The Villages

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Air conditioning
  • Private garden
Our beautifully fully furnished patio villa in the village of Hemingway is fully stocked and ready for move-in. Tastefully furnished in tradition style, you will feel at home in our home away from home. The open floor plan is inviting. The screened porch lets you enj …see more

from $50 / night

$350 / week

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from $50 / night

13

Vacation home in The Villages

Florida / The Villages

2 4 30 nights min

  • 2 bedrooms
  • Sleeps 4
  • 30 nights min
  • Air conditioning
  • Pet friendly
  • Private garden
Closest Courtyard Villa neighborhood to Lake Sumter Landing Welcome to 1086 Peninsula! - a beautiful, professionally decorated Courtyard Villa in Lake Sumter Landing's Creekside Neighborhood. Your home-away-from-home is literally a 7 minute walk to Lake Sumter Landing …see more

from $117 / night

$817 / week

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from $117 / night

(1) Excellent 

12

The Villages Vacation home rental

Florida / The Villages

3 5 Min stay varies

  • 3 bedrooms
  • Sleeps 5
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
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 rec …see more

from $50 / night

$350 / week

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from $50 / night

(1) Excellent 

13

The Villages Vacation villa rental

Florida / The Villages

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Air conditioning
Beautiful fully furnished patio villa in the Village of Hemingway. Centrally located with all the amenities. Gas grill, king bed in master, all linens included. Short drive to Sumter Landing, yet near Colony Recreation Center. Colony shopping plaza just minutes away …see more

from $60 / night

$330 - $475 / week

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from $60 / night

(2) Excellent 

28

Vacation home in The Villages

Florida / The Villages

2 4 7 nights min

  • 2 bedrooms
  • Sleeps 4
  • 7 nights min
  • Child friendly
  • Air conditioning
  • Private garden
This is just the Perfect Patio Villa with stunning, enhanced landscaping a. Our home is super clean and in Pristine condition. Inside the spacious Open Floor Plan, the neutral colors are so inviting that entertaining family and friends will be at the top of your list. T …see more

from $99 / night

$693 - $1,393 / week

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from $99 / night

28

Vacation home in The Villages

Florida / The Villages

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
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, g …see more

from $85 / night

$595 / week

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from $85 / night