Vacation Rentals with Pool in The Villages Market Square, FL: Compare 10+ Sites & Save

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  2. Vacation Rentals with Pool
  3.  USA

  4.  Florida
  5.  Leesburg

  6.  The Villages Market Square

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255 Best Vacation Rentals with Pool in The Villages Market Square (Starting from $110)

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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Sunshine Stay a Creekside Villa at Lake Sumter Landing with Nature & Water Views
Sunshine Stay a Creekside Villa at Lake Sumter Landing with Nature & Water Views
Villa
The Villages, FL, 32162, United States
0.4k from The Villages Market Square center

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

3 Bedrooms7 Guests
10.0

Exceptional

11 reviews

$208
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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Our Village Gem-Dog Friendly-Cozy & Peaceful-Walk to Sumter Square
Our Village Gem-Dog Friendly-Cozy & Peaceful-Walk to Sumter Square
House
The Villages, FL, 32162, United States
0.5k from The Villages Market Square center

AC, Barbecue, Business Services, Dryer, Extra Bed, Free Parking, Heater, Internet, Kitchen

2 Bedrooms6 Guests
10.0

Exceptional

123 reviews

$154
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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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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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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Charming 3-bedroom villa walking distance to Lake Sumter Sq  Golf Cart included
Charming 3-bedroom villa walking distance to Lake Sumter Sq Golf Cart included
Villa
The Villages, FL, 32162, United States
0.6k from The Villages Market Square center

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

3 Bedrooms6 Guests
New to Booking
$187
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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Walk to Sumter Landing-New Listing-Golf Cart-Pet Friendly
Walk to Sumter Landing-New Listing-Golf Cart-Pet Friendly
Villa
The Villages, FL, 32162, United States
0.6k from The Villages Market Square center

AC, Dryer, Fitness Equipment, Free Parking, Heater, Internet, Kitchen, Laundry, No Smoking

2 Bedrooms4 Guests
10.0

Exceptional

7 reviews

$154
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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Walk to Lake Sumter Landing! Our Village Gem - 10 Star - w/ Golf Cart
Walk to Lake Sumter Landing! Our Village Gem - 10 Star - w/ Golf Cart
House
The Villages, FL, 32162, United States
0.8k from The Villages Market Square center

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

2 Bedrooms6 Guests
10.0

Exceptional

120 reviews

$152
Average price / night
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TikiTiki walk/ride 2 Lake Sumter *Pool & Hot Tub*
TikiTiki walk/ride 2 Lake Sumter *Pool & Hot Tub*
House
Cherry Lake, FL, USA
2.1k from The Villages Market Square center

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

3 Bedrooms8 Guests
New to Booking
$361
Average price / night
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Designer 3 bedroom high-end home with walking distance to Lake Sumter Landing
Designer 3 bedroom high-end home with walking distance to Lake Sumter Landing
House
The Villages, FL, 32162, United States
1.2k from The Villages Market Square center

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

3 Bedrooms6 Guests
9.8

Exceptional

7 reviews

$363
Average price / night
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TranquilBlue Retreat
TranquilBlue Retreat
Villa
The Villages, FL, USA
2.5k from The Villages Market Square center

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

2 Bedrooms4 Guests
8.5

Very Good

2 reviews

$232
Average price / night
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WELCOME TO ART & SUE'S 3/2 PLACE. HEATED POOL COURT YD VILLA NEAR SUMTER LANDING
WELCOME TO ART & SUE'S 3/2 PLACE. HEATED POOL COURT YD VILLA NEAR SUMTER LANDING
House
The Villages, FL, 32162, United States
1.3k from The Villages Market Square center

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

3 Bedrooms6 Guests
10.0

Exceptional

1 reviews

$144
Average price / night
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Single-Story Home with Golf Cart in The Villages
Single-Story Home with Golf Cart in The Villages
House
The Villages, FL, USA
2.5k from The Villages Market Square center

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

3 Bedrooms6 Guests
New to Booking
$173
Average price / night
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COMFORT & CHARM AWAIT IN THIS MALLORY VILLAGE HOME JUST MINS TO SUMTER LANDING!
COMFORT & CHARM AWAIT IN THIS MALLORY VILLAGE HOME JUST MINS TO SUMTER LANDING!
House
The Villages, FL, 32162, United States
1.8k from The Villages Market Square center

AC, Barbecue, Dryer, Free Parking, Heater, Laundry, Microwave, No Smoking, Pool

3 Bedrooms6 Guests
New to Booking
$168
Average price / night
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Sunny Home with Golf Cart in The Villages!
Sunny Home with Golf Cart in The Villages!
House
The Villages, FL, USA
2.5k from The Villages Market Square center

Cheap, Accommodations, Pools, Parking, Villas, Vacation homes, Spa, Cottages, Lodgings

3 Bedrooms6 Guests
10.0

Exceptional

3 reviews

$274
Average price / night
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Salted Rim - 3/2 in The Village of Sunset Pointe
Salted Rim - 3/2 in The Village of Sunset Pointe
House
Sunset Pointe, The Villages, FL, 32162, United States
1.9k from The Villages Market Square center

AC, Dryer, Free Parking, Heater, Internet, Kitchen, Microwave, No Smoking, Patio

3 Bedrooms6 Guests
10.0

Exceptional

1 reviews

$217
Average price / night
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🧡Gorgeous Waterfront Oasis In Heart of The Villages 2 BR, 2 BA
🧡Gorgeous Waterfront Oasis In Heart of The Villages 2 BR, 2 BA
House
Lady Lake, FL, 32159, United States
1.9k from The Villages Market Square center

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

2 Bedrooms8 Guests
9.8

Exceptional

18 reviews

$320
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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3 bed Courtyard Villa, Private Putting Green, Sumter Landing, 2 gas golf carts.
3 bed Courtyard Villa, Private Putting Green, Sumter Landing, 2 gas golf carts.
Villa
The Villages, FL, 32162, United States
2.0k from The Villages Market Square center

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

3 Bedrooms4 Guests
10.0

Exceptional

31 reviews

$179
Average price / night
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Superb location, 2 bedroom, 2 bath home with a office. Near Sumter Landing
Superb location, 2 bedroom, 2 bath home with a office. Near Sumter Landing
House
The Villages, FL, 32162, United States
2.1k from The Villages Market Square center

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

2 Bedrooms4 Guests
New to Booking
$156
Average price / night
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TikiTiki Lake Sumter, private pool, hot tub, game room, outdoor kitchen&tiki bar
TikiTiki Lake Sumter, private pool, hot tub, game room, outdoor kitchen&tiki bar
House
The Villages, FL, 32162, United States
2.1k from The Villages Market Square center

AC, Arcade, Barbecue, Crib, Dryer, Fireplace, Free Parking, Heater, Hot Tub

3 Bedrooms8 Guests
10.0

Exceptional

4 reviews

$297
Average price / night
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WOW...ELEGANT... Courtyard VILLA + Golf CART, Steps to POOL, 3 Min to Sumter SQ
WOW...ELEGANT... Courtyard VILLA + Golf CART, Steps to POOL, 3 Min to Sumter SQ
Villa
The Villages, FL, 32162, United States
2.1k from The Villages Market Square center

AC, Business Services, Dryer, Extra Bed, Free Parking, Heater, Internet, Kitchen, Laundry

2 Bedrooms6 Guests
9.4

Superb

92 reviews

$141
Average price / night
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Cozy Villages villa, 2 bed, 2 bath. Great Location
Cozy Villages villa, 2 bed, 2 bath. Great Location
House
The Villages, FL, 32159, United States
2.2k from The Villages Market Square center

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

2 Bedrooms4 Guests
10.0

Exceptional

49 reviews

$110
Average price / night
Check Availability

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 Vacation Rentals with Pool in The Villages Market Square.

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

The Villages Market Square Vacation Rentals with Pool on the Map

Frequently Asked Questions

You can explore 255 verified vacation rentals with a pool in The Villages Market Square. These include a wide range of private homes, villas, and condos that offer on-site swimming facilities for a more relaxing stay.

Prices for vacation rentals with a pool in The Villages Market Square vary depending on the season, property size, and whether the pool is private or shared. Rates typically start from around $110 per night, with private pool homes and peak travel periods often costing more.

Many rentals in The Villages Market Square offer private pools for exclusive use, while others provide access to shared or community pools. You can use filters to specifically find properties with private pools if that is your preference.

Yes, some vacation rentals with pools in The Villages Market Square welcome pets. Currently, 45 listings allow pets, although policies may vary by property. It’s a good idea to review any rules related to pets around pool areas before booking.

Properties with pools are often in high demand, especially during warmer months and holidays, so booking 90 to 120 days in advance is recommended for the best selection. During off-peak seasons, you may still find availability closer to your travel dates.

Vacation rentals with pools in The Villages Market Square often include additional outdoor features such as Pool, Fireplace/Heating, and Wellness Facilities. These amenities enhance comfort and make it easier to enjoy outdoor living during your stay.

Some vacation rentals in The Villages Market Square offer heated pools, which can be especially useful during cooler months. In certain cases, pool heating may be available for an additional fee, so it’s best to check the property details before booking.