50 Best The Villages Apartments on Holiday Lettings - Vacation rentals

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156 Vacation rentals

25

Home rental in The Villages

Florida / The Villages

3 5 Min stay varies

  • 3 bedrooms
  • Sleeps 5
  • Min stay varies
  • Air conditioning
  • Private garden
Large 3 bedroom, overlooking lake, corner of Cul-de-sac street. Eat-in kitchen with cherry cabinets, 3 high definition televisions,, Wireless internet, phone and cable all included. Fun Reclining chairs to enjoy while reading or watching TV. Tile & beautiful samba plank …see more

from $93 / night

$800 / week

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from $93 / night

(5) 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 $79 / night

$530 - $790 / week

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from $79 / night

17

Vacation home in The Villages

Florida / The Villages

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Swimming pool
  • Ask about children
  • Air conditioning
Location! Location! This private courtyard villa comes completely furnished with everything you need to have a relaxing vacation. Beautifully decorated, ceiling fans in every room, , tiles through the livingroom and Masterbedroom, tiles through kitchen and …see more

from $100 / night

$450 - $780 / week

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from $100 / night

(2) 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 $59 / night

$399 - $575 / week

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from $59 / night

21

The Villages Vacation home rental

Florida / The Villages

3 6 7 nights min

  • 3 bedrooms
  • Sleeps 6
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
Location, Location, Location....This beautiful home is located in the beautiful neighborhood of Caroline where you're surrounded by golf courses and recreation centers. Mallory Country Club is about a mile away and offers Championship golf and has one of the most popula …see more

from $115 / night

$805 - $980 / week

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from $115 / night

(3) Very Good 

13

The Villages Vacation home accommodation

Florida / The Villages

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Swimming pool
  • Ask about children
  • 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

24

Vacation home accommodation

Florida / The Villages

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
FREE golf, cart, wifi, cable, printer/fax, swim, grill, live music, FIDO and much more with resident ID cards! In The Villages, Florida ALL locations are great, as everything is never more than a 30 minute drive away, with most of it accessible by golf cart.  Nestled in …see more

from $70 / night

$490 - $665 / week

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from $70 / night

(1) 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 - $599 / week

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from $59 / night

19

Vacation home in The Villages

Florida / The Villages

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Child friendly
Location, Location, Location! This beautiful home is located in the neighborhood of Liberty Park where you're surrounded by golf courses and recreation centers. Cane Garden Country Club is about a mile away and offers Championship golf and has one of the most popular co …see more

from $75 / night

$525 - $665 / week

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from $75 / night

19

Vacation villa in The Villages

Florida / The Villages

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Nearest beach 97 mi
  • Swimming pool
  • Ask about children
Looking for a villa very close to shopping, a town square and recreation? This beauty is located just a few short blocks from golf car accessible shopping plazas, the Chula Vista Recreation Center with swimming, indoor and outdoor sports/clubs, executive golf and the po …see more

from $100 / night

$600 - $700 / week

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from $100 / night

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! With room for 6 guests, a tranquil atmosphere with screened patio, and access to a community pool, this house has it all! From the moment …see more

from $99 / night

$594 - $1200 / week

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from $99 / night

(2) Excellent 

8

Vacation home in The Villages

Florida / The Villages

2 4 14 nights min

  • 2 bedrooms
  • Sleeps 4
  • 14 nights min
  • Child friendly
  • Car not necessary
  • Air conditioning
Fantastic 2 bedroom/2 bath fully furnished site-built home situated on an oversized homesite with open acreage at the rear. The kitchen has an island with a granite countertop, a pantry, and oak cabinets. Tile floors enhance the kitchen, florida room, hallway and baths. …see more

from $100 / night

$600 - $776 / week

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from $100 / night

23

Vacation home in The Villages

Florida / The Villages

3 6 7 nights min

  • 3 bedrooms
  • Sleeps 6
  • 7 nights min
  • Child friendly
Location, Location, Location! This beautiful 2 bedroom home is located in the desirable community of Virginia Trace. You can walk to Lake Sumter Landing Market Square where you will find shopping, restaurants, movie theaters and FREE live entertainment nightly. Arnold P …see more

from $110 / night

$770 - $805 / week

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from $110 / night

9

The Villages Vacation villa rental

Florida / The Villages

2 4 3 nights min

  • 2 bedrooms
  • Sleeps 4
  • 3 nights min
  • Child friendly
  • Air conditioning
WEEKLY AND MONTHLY PRICE SAVINGS!!! This Patio Villa is PERFECTLY located between Town Squares: Spanish Springs and Sumter Landing!! This 2 Bedroom/2 Full Bath Villa has: Full linens, washer/dryer and fully functional kitchen. It has central air and an enclosed lanai. …see more

from $125 / night

$700 / week

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from $125 / night

17

Vacation home rental

Florida / The Villages

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • 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 $200 / night

$925 / week

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from $200 / night

26

Vacation home in The Villages

Florida / The Villages

3 6 7 nights min

  • 3 bedrooms
  • Sleeps 6
  • 7 nights min
  • Child friendly
SUMMER DATES AVAILABLE - Call today to book your stay in this beautiful Pool Home! This beautifully decorated 3 bedroom home is located in one of the newer neighborhoods. Dunedin is conveniently located between Lake Sumter Landing Market Square and Brownwood Paddock Squ …see more

from $125 / night

$875 / week

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from $125 / night

17

Vacation home 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
Location, Location, Location....This beautiful home is located in the desirable neighborhood of Sable Chase. You're minutes by golf cart to Lake Sumter Landing Market Square where you can find shopping, restaurants, movie theaters and FREE live entertainment nightly. Ma …see more

from $110 / night

$770 - $840 / week

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from $110 / night

23

Vacation home rental

Florida / The Villages

2 6 Min stay varies

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies
  • Child friendly
This beautiful home is located in the desirable neighborhood of Lynnhaven. You're minutes to Lake Sumter Landing Market Square where you can find shopping, restaurants, movie theaters and FREE live entertainment nightly. Arnold Palmer Legends Country Club is about two a …see more

from $70 / night

$490 - $665 / week

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from $70 / night

(2) Very Good 

19

Vacation home with shared pool in The Villages

Florida / The Villages

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
LOCATION! LOCATION! LOCATION! This beautifully decorated 2 bedroom villa is located on the first tee box of De La Vista golf course in one of the most desirable neighborhoods. The Village of Tierra Del Sol is conveniently located approximately 1.5 miles to Lake Sumter L …see more

from $75 / night

$525 - $665 / week

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from $75 / night

16

Vacation home with shared pool in The Villages

Florida / The Villages

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
**Golf Cart Rental Discount Available** Please let us know at time of reservation to receive the discount This beautifully decorated 2 bedroom 2 Bathroom home is located in one of the most desirable neighborhoods. Duval is conveniently located between Lake Sumter Landin …see more

from $75 / night

$525 - $665 / week

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from $75 / 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

(1) Excellent 

18

Vacation home in The Villages

Florida / The Villages

2 4 7 nights min

  • 2 bedrooms
  • Sleeps 4
  • 7 nights min
  • Child friendly
  • Pet friendly
LOCATION, LOCATION, LOCATION!...This beautiful village home is located in the desirable neighborhood of Chatham where you're minutes away by golf cart to shopping, restaurants, recreation and golfing.  You're a short walk to the Chatham Square Recreation Center where yo …see more

from $85 / night

$595 / week

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from $85 / night

17

Vacation home with shared pool in The Villages

Florida / The Villages

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
This beautiful home is located in the desirable neighborhood of Bonnybrook. You're minutes by golf cart to Lake Sumter Landing Market Square where you will find shopping, restaurants, movie theaters and FREE live entertainment nightly. When you are ready to hit the link …see more

from $80 / night

$560 - $700 / week

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from $80 / night

28

Home rental in The Villages

Florida / The Villages

3 6 30 nights min

  • 3 bedrooms
  • Sleeps 6
  • 30 nights min
  • Child friendly
This beautifully decorated 3 bedroom 2 1/2 Bathroom home is located in one of the most desirable neighborhoods. Duval is conveniently located between Lake Sumter Landing and Brownwood Paddock Square. The Town Squares are one of the most popular attractions in the commun …see more

from $52 / night

$362 / week

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from $52 / night

23

The Villages Vacation home rental

Florida / The Villages

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Child friendly
LOCATION, LOCATION, LOCATION!....This beautiful home is located in the desirable neighborhood of Piedmont where you're minutes by golf cart to shopping, restaurants, recreation & golfing.  You're a short distance to the Chatham Square Recreation Center where you'll find …see more

from $110 / night

$770 - $840 / week

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from $110 / night

(1) Very Good 

23

The Villages Vacation home rental

Florida / The Villages

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
Location, Location,  beautiful 3 bedroom home is located in the desirable neighborhood of Virginia Trace. You can walk to Lake Sumter Landing Market Square where you will find shopping, restaurants, movie theaters and FREE live entertainment nightly. Arnold Palmer Count …see more

from $125 / night

$875 - $1050 / week

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from $125 / night

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

21

Home rental in The Villages with shared pool

Florida / The Villages

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
This beautifully decorated 3 bedroom home is located in one of the newer neighborhoods.  Charlotte is conveniently located between Lake Sumter Landing Market Square and Brownwood Paddock Square.  The Town Squares are one of the most popular attractions of the community …see more

from $110 / night

$770 - $840 / week

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from $110 / night

18

The Villages Vacation home rental

Florida / The Villages

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
This beautifully decorated Courtyard Villa with 2 king bedrooms and a den is located in the neighborhood of Sanibel just south of Rt 466A off Morse Blvd.. This PET FRIENDLY (cat & dog friendly) home comes complete with WIFI internet.  Across the street is the Sanibel ne …see more

from $110 / night

$770 - $868 / week

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from $110 / night

(1) Very Good 

21

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
This brand new courtyard villa home is situated in the southern end of the community, your location is ideal for enjoying all the activities in Brownwood Paddock Square, the newest of the three town centers. A short golf cart ride puts you in the heart of FREE nightly e …see more

from $110 / night

$770 - $840 / week

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from $110 / night

19

Vacation home in The Villages

Florida / The Villages

2 4 7 nights min

  • 2 bedrooms
  • Sleeps 4
  • 7 nights min
  • Child friendly
  • Pet friendly
This beautifully decorated 2 bedroom 2 Bathroom villa is located in one of the most sought out neighborhoods. St. James is conveniently located between Lake Sumter Landing Market Square and Brownwood Paddock Square. The Town Squares are one of the most popular attractio …see more

from $70 / night

$490 / week

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from $70 / night

15

Vacation home with shared pool in The Villages

Florida / The Villages

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
This beautifully decorated 2 bedroom home is located in one of the newer neighborhoods. Fernandina is conveniently located between Lake Sumter Landing Market Square and Brownwood Paddock Square. The Town Squares are one of the most popular attractions of the community w …see more

from $70 / night

$490 - $665 / week

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from $70 / night

(2) Very Good 

8

Vacation home with shared pool in The Villages

Florida / The Villages

2 6 7 nights min

  • 2 bedrooms
  • Sleeps 6
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Car not necessary
This nicely decorated home is located in the desirable Village of Hadley where you're surrounded by golf courses and recreation centers. Havana Country Club is minutes by golf cart and offers Championship golf, a pro shop and a very popular country club restaur …see more

from $123 / night

$861 / week

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from $123 / night

21

The Villages Vacation home rental

Florida / The Villages

2 4 7 nights min

  • 2 bedrooms
  • Sleeps 4
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
Location, Location, Location....This beautiful home is located in the neighborhood of Virginia Trace where you're surrounded by golf courses and recreation centers. Mallory Country Club is less than a mile away and offers Championship golf and has one of the most popula …see more

from $75 / night

$525 - $665 / week

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from $75 / night

22

Home rental in The Villages with shared pool

Florida / The Villages

3 8 7 nights min

  • 3 bedrooms
  • Sleeps 8
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
Location, Location, Location! This beautiful 3 bedroom home is located in the desirable community of Virginia Trace. You can walk to Lake Sumter Landing Market Square where you will find shopping, restaurants, movie theaters and FREE live entertainment nightly. Arnold P …see more

from $125 / night

$875 / week

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from $125 / night

17

Vacation home in The Villages

Florida / The Villages

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
This beautifully decorated home is located in the desirable neighborhood of Hemingway where you're surrounded by golf courses and recreation centers. Havana Country Club is minutes by golf cart and offers Championship golf, a pro shop and a very popular country club res …see more

from $85 / night

$595 - $700 / week

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from $85 / night

27

Vacation home in The Villages

Florida / The Villages

3 6 7 nights min

  • 3 bedrooms
  • Sleeps 6
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
SUMMER DATES AVAILABLE - Call today to book your stay in this beautiful Pool Home! This beautifully decorated 3 bedroom home is located in one of the newer neighborhoods. Sanibel is conveniently located between Lake Sumter Landing Market Square and Brownwood Paddock Squ …see more

from $115 / night

$805 - $1050 / week

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from $115 / night

17

The Villages Vacation home rental

Florida / The Villages

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
Location, Location, Location....This beautiful home is located in the beautiful neighborhood of MALLORY SQUARE where you're surrounded by golf courses and recreation centers. Mallory Country Club is about a half mile away and offers Championship golf and has one of the …see more

from $110 / night

$770 - $840 / week

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from $110 / night

25

Home rental in The Villages

Florida / The Villages

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Child friendly
This beautifully decorated 3 bedroom villa is located in the neighborhood of St James and is conveniently located between Lake Sumter Landing Market Square and Brownwood at Paddock Park where you'll find restaurants, movie theaters, shopping, FREE live music and dancing …see more

from $110 / night

$770 - $840 / week

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from $110 / night

8

Vacation home with shared pool in The Villages

Florida / The Villages

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
This cute and cozy home is located in the neighborhood of Summerhill.  Location! Location! Location!  You're within walking distance to Dunkin Donuts, I-Hop, Publix, CVS, Bealls Dept Store & more.  By golf cart you're minutes to Wal-Mart and restaurants like Bone Fish G …see more

from $70 / night

$490 - $665 / week

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from $70 / night

1