Family-Friendly Vacation Rentals in The Villages Market Square, FL: Compare 10+ Sites & Save

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  6.  The Villages Market Square

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221 Best Family Vacation Rentals in The Villages Market Square (Starting from $113)

The Gardenia House
The Gardenia House
House
The Villages, FL, USA
0.5k from The Villages Market Square center

Cheap, Accommodations, Pools, Villas, Vacation homes, Cottages, Pet-friendly, Lodgings, Places to stay

3 Bedrooms6 Guests
10.0

Exceptional

4 reviews

$257
Average price / night
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Stunning 2/2 Villa in Creekside Landing adjacent to Lake Sumter Landing w/Cart
Stunning 2/2 Villa in Creekside Landing adjacent to Lake Sumter Landing w/Cart
Villa
The Villages, FL, 32162, United States
0.5k from The Villages Market Square center

AC, Barbecue, Dryer, Fitness Equipment, Free Parking, Heater, Internet, Kitchen, Laundry

2 Bedrooms4 Guests
10.0

Exceptional

78 reviews

$178
Average price / night
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Bancroft - Walking Distance To Sumter SquareVillagepeople
Bancroft - Walking Distance To Sumter SquareVillagepeople
House
The Villages, FL, USA
0.6k from The Villages Market Square center

Accommodations, Pools, Villas, Vacation homes, Cottages, Lodgings, Vacation rentals, Places to stay

3 Bedrooms6 Guests
New to Booking
$239
Average price / night
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Welcome Small DOGS.. ELEGANT Villa, GOLF CART, Walk to Sumter Square, sleep 6
Welcome Small DOGS.. ELEGANT Villa, GOLF CART, Walk to Sumter Square, sleep 6
Villa
The Villages, FL, 32162, United States
0.6k from The Villages Market Square center

AC, Dryer, Extra Bed, Free Parking, Heater, Internet, Kitchen, Laundry, Living Area

2 Bedrooms8 Guests
9.6

Exceptional

127 reviews

$166
Average price / night
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Solar Powered in Virginia Trace
Solar Powered in Virginia Trace
House
The Villages, FL, USA
0.6k from The Villages Market Square center

Accommodations, Parking, Villas, Vacation homes, Cottages, Lodgings, Places to stay

3 Bedrooms6 Guests
New to Booking
$165
Average price / night
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Perfect Location 2/2 Villa in Creekside Landing walking distance to Lake Sumter
Perfect Location 2/2 Villa in Creekside Landing walking distance to Lake Sumter
Villa
The Villages, FL, 32162, United States
0.7k from The Villages Market Square center

AC, Barbecue, Dryer, Free Parking, Hot Tub, Internet, Kitchen, Laundry, Microwave

2 Bedrooms4 Guests
10.0

Exceptional

18 reviews

$147
Average price / night
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1106 Z3A VILLAGE OF BRIDGEPORT at CREEKSIDE LANDING by REMAX Premier
1106 Z3A VILLAGE OF BRIDGEPORT at CREEKSIDE LANDING by REMAX Premier
Villa
The Villages, FL, USA
0.6k from The Villages Market Square center

Accommodations, Parking, Villas, Vacation homes, Cottages, Pet-friendly, Lodgings, Places to stay

3 Bedrooms6 Guests
New to Booking
$241
Average price / night
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MONTHLY RATES/SUMTER AREA/SCREEN CAGE/GOLF CART/TANKLESS HOT WATER/GRANITE/KING
MONTHLY RATES/SUMTER AREA/SCREEN CAGE/GOLF CART/TANKLESS HOT WATER/GRANITE/KING
Villa
The Villages, FL, 32162, United States
1.9k from The Villages Market Square center

AC, Barbecue, Crib, Dryer, Free Parking, Heater, Internet, Kitchen, Laundry

2 Bedrooms2 Guests
10.0

Exceptional

32 reviews

$159
Average price / night
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Reidville - Patio Villa Near Sumter Landing- Villagepeople
Reidville - Patio Villa Near Sumter Landing- Villagepeople
House
The Villages, FL, USA
1.2k from The Villages Market Square center

Accommodations, Parking, Villas, Vacation homes, Cottages, Pet-friendly, Lodgings, Places to stay

2 Bedrooms4 Guests
New to Booking
$113
Average price / night
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Caddy Shack 1, The Villages, near Sumter Landing 3 BD / 2 BA with golf cart
Caddy Shack 1, The Villages, near Sumter Landing 3 BD / 2 BA with golf cart
House
The Villages, FL, 32162, United States
1.9k from The Villages Market Square center

AC, Barbecue, Dryer, Free Parking, Heater, Internet, Kitchen, Laundry, Living Area

3 Bedrooms7 Guests
10.0

Exceptional

25 reviews

$225
Average price / night
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Home with Resort Amenities in The Villages
Home with Resort Amenities in The Villages
House
The Villages, FL, USA
1.8k from The Villages Market Square center

Accommodations, Parking, Villas, Vacation homes, Cottages, Lodgings, Places to stay

2 Bedrooms4 Guests
New to Booking
$169
Average price / night
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Exceptional Villa Close to Everything – Live Music, Dining & More!
Exceptional Villa Close to Everything – Live Music, Dining & More!
House
The Villages, FL, 32159, United States
2.0k from The Villages Market Square center

AC, Barbecue, Dryer, Fitness Equipment, Free Parking, Heater, Internet, Kitchen, Laundry

2 Bedrooms4 Guests
9.8

Exceptional

63 reviews

$157
Average price / night
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1433 Z3a VILLAGE OF SUNSET POINTE by REMAX Premier
1433 Z3a VILLAGE OF SUNSET POINTE by REMAX Premier
House
The Villages, FL, USA
1.8k from The Villages Market Square center

Accommodations, Parking, Villas, Vacation homes, Cottages, Pet-friendly, Lodgings, Places to stay

3 Bedrooms6 Guests
New to Booking
$227
Average price / night
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When Quality & Location Matter
When Quality & Location Matter
Villa
The Villages, FL, 32159, United States
2.2k from The Villages Market Square center

AC, Balcony, Dryer, Extra Bed, Free Parking, Heater, Internet, Kitchen, Laundry

2 Bedrooms6 Guests
9.8

Exceptional

11 reviews

$148
Average price / night
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Renovated Villa Btwn Lake Sumter and Spanish Springs
Renovated Villa Btwn Lake Sumter and Spanish Springs
House
The Villages, FL, USA
2.0k from The Villages Market Square center

Accommodations, Pools, Parking, Villas, Vacation homes, Cottages, Lodgings, Hot tubs, Places to stay

1 Bedroom5 Guests
New to Booking
$196
Average price / night
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Casita of the Setting Sun- 1/1 Guest House w/ Pool Access, Golf Cart & Stunning View of Amelia Championship Golf Course
Casita of the Setting Sun- 1/1 Guest House w/ Pool Access, Golf Cart & Stunning View of Amelia Championship Golf Course
Cottage
Amelia, The Villages, FL, 32162, United States
2.3k from The Villages Market Square center

AC, Barbecue, Dryer, Free Parking, Heater, Hot Tub, Internet, Kitchen, Laundry

1 Bedroom2 Guests
9.6

Exceptional

7 reviews

$286
Average price / night
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Olanta - Patio Villa Near Lake SumterVillagepeople
Olanta - Patio Villa Near Lake SumterVillagepeople
Villa
The Villages, FL, USA
2.1k from The Villages Market Square center

Cheap, Accommodations, Villas, Vacation homes, Cottages, Lodgings, Vacation rentals, Places to stay

3 Bedrooms6 Guests
10.0

Exceptional

3 reviews

$165
Average price / night
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Fabulous Courtyard Villa 1 mile to Sumter Landing
Fabulous Courtyard Villa 1 mile to Sumter Landing
Villa
The Villages, FL, 32162, United States
2.4k from The Villages Market Square center

AC, Barbecue, Dryer, Free Parking, Heater, Hot Tub, Internet, Kitchen, Laundry

2 Bedrooms4 Guests
10.0

Exceptional

4 reviews

$304
Average price / night
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Sonora - Patio Villa By Spanish SpringsVillagepeople
Sonora - Patio Villa By Spanish SpringsVillagepeople
Villa
The Villages, FL, USA
2.1k from The Villages Market Square center

Accommodations, Pools, Villas, Vacation homes, Cottages, Pet-friendly, Lodgings, Vacation rentals, Places to stay

2 Bedrooms4 Guests
New to Booking
$194
Average price / night
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Dreamscape - 3/2 w/ Private Pool On the Golf Course in The Village of Poinciana
Dreamscape - 3/2 w/ Private Pool On the Golf Course in The Village of Poinciana
House
The Villages, FL, 32162, United States
2.6k from The Villages Market Square center

AC, Barbecue, Dryer, Free Parking, Heater, Hot Tub, Internet, Kitchen, Laundry

3 Bedrooms5 Guests
9.6

Exceptional

14 reviews

$292
Average price / night
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WOW CLOSED IN COURTYARD VILLA, GOLF CART, 2 BEDROOMS AND WALK TO 5 LOCAL POOLS.
WOW CLOSED IN COURTYARD VILLA, GOLF CART, 2 BEDROOMS AND WALK TO 5 LOCAL POOLS.
Villa
The Villages, FL, 32162, United States
2.6k from The Villages Market Square center

AC, Barbecue, Dryer, Free Parking, Heater, Internet, Kitchen, Laundry, Microwave

2 Bedrooms6 Guests
10.0

Exceptional

33 reviews

$492
Average price / night
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Stop and Smell the Roses - 3/2 w/ Golf Cart in The Village of Poinciana
Stop and Smell the Roses - 3/2 w/ Golf Cart in The Village of Poinciana
House
The Villages, FL, 32162, United States
2.7k from The Villages Market Square center

AC, Barbecue, Dryer, Free Parking, Heater, Internet, Kitchen, Laundry, Microwave

3 Bedrooms6 Guests
9.0

Fabulous

2 reviews

$226
Average price / night
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Unique Villa w/Huge Patio - Includes Golf Cart
Unique Villa w/Huge Patio - Includes Golf Cart
Villa
The Villages, FL, 32159, United States
2.7k from The Villages Market Square center

AC, Barbecue, Dryer, Fitness Equipment, Free Parking, Heater, Internet, Kitchen, Laundry

2 Bedrooms6 Guests
10.0

Exceptional

1 reviews

$202
Average price / night
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Margaritaville - 3/2 w/ Private POOL & GOLF CART in The Village of Amelia
Margaritaville - 3/2 w/ Private POOL & GOLF CART in The Village of Amelia
House
The Villages, FL, 32162, United States
2.7k from The Villages Market Square center

AC, Barbecue, Dryer, Elevator, Free Parking, Heater, Internet, Kitchen, Laundry

3 Bedrooms6 Guests
9.0

Fabulous

13 reviews

$329
Average price / night
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Everything! 3/2, FREE golf & 4-seat cart, RESIDENT passes, pets, Lake Sumter Sq.
Everything! 3/2, FREE golf & 4-seat cart, RESIDENT passes, pets, Lake Sumter Sq.
House
The Villages, FL, 32162, United States
2.7k from The Villages Market Square center

AC, Arcade, Barbecue, Dryer, Extra Bed, Free Parking, Heater, Internet, Kitchen

3 Bedrooms6 Guests
10.0

Exceptional

66 reviews

$202
Average price / night
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Palm Breeze Oasis-3/2 w/ Private Pool & Golf Cart in The Village of Liberty Park
Palm Breeze Oasis-3/2 w/ Private Pool & Golf Cart in The Village of Liberty Park
House
Liberty Park, The Villages, FL, 32162, United States
2.8k from The Villages Market Square center

AC, Barbecue, Dryer, Free Parking, Heater, Internet, Kitchen, Laundry, Microwave

3 Bedrooms6 Guests
9.4

Superb

3 reviews

$360
Average price / night
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Coastline Canvas - 2/2 w/ Golf Cart in The Village of  Bonita
Coastline Canvas - 2/2 w/ Golf Cart in The Village of Bonita
House
Bonita, The Villages, FL, 32162, United States
3.2k from The Villages Market Square center

AC, Barbecue, Dryer, Free Parking, Heater, Internet, Kitchen, Laundry, Microwave

2 Bedrooms4 Guests
9.6

Exceptional

9 reviews

$244
Average price / night
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Pro Tip:
VacationByOwnerRentals aggregates the best inventory from leading travel sites, including Booking.com, Agoda.com, Expedia.com, Vrbo.com, and Airbnb.com. Use our Advanced Filters to compare verified homes, villas, cabins, condos, cottages, vacation rentals, hotels, and eco-friendly stays. Our goal is to help you find the absolute best Family Vacation Rentals in The Villages Market Square.

Where to stay in The Villages Market Square? Best neighborhoods & areas

The Villages Market Square Family Vacation Rentals on the Map

Frequently Asked Questions

You can explore 221 verified family-friendly vacation rentals in The Villages Market Square. These include spacious homes, villas, and condos designed to accommodate families of different sizes.

Prices for family-friendly rentals in The Villages Market Square vary depending on the season, number of bedrooms, and included amenities. Rates typically start from around $113 per night, with larger homes and peak travel periods often costing more.

Many family-friendly rentals in The Villages Market Square offer baby-friendly items such as high chairs, cribs, or pack-and-play options. Availability can vary, so it’s helpful to check the listing details before booking.

Yes, some rentals in The Villages Market Square are well suited for multi-generational stays, offering multiple bedrooms, separate living areas, and enough space for larger groups to stay comfortably together.

For busy travel periods such as school holidays or summer breaks, booking 90 to 120 days in advance is recommended to secure the best options. Availability may be more flexible during quieter times of the year.

Family-friendly rentals in The Villages Market Square often include amenities such as Child Friendly, Fireplace/Heating, and Wellness Facilities. These features help make stays more convenient and enjoyable for both adults and children.

You can use search filters to find rentals that offer features like game rooms, playgrounds, or entertainment areas. Checking property descriptions can also help you identify homes that are well suited for families with children.