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Holiday Rentals in The Villages

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292 rentals in The Villages.
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Stunning Private Designer Home: Pool, Spa, Golf View, Walk to Square, holiday rental in The Villages
Stunning Private Designer Home: Pool, Spa, Golf View, Walk to Square, holiday rental in The Villages
Stunning Private Designer Home: Pool, Spa, Golf View, Walk to Square, holiday rental in The Villages

Stunning Private Designer Home: Pool, Spa, Golf View, Walk to Square

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
More info
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3/2.5 Golf Front Home and Solar Heat Pool!  Awesome View, FREE  golf cart, wif, holiday rental in The Villages
3/2.5 Golf Front Home and Solar Heat Pool!  Awesome View, FREE  golf cart, wif, holiday rental in The Villages
3/2.5 Golf Front Home and Solar Heat Pool!  Awesome View, FREE  golf cart, wif, holiday rental in The Villages

3/2.5 Golf Front Home and Solar Heat Pool! Awesome View, FREE golf cart, wif

Holiday Rental House
3 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
More info
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Beautiful 3/2 Villa in Virginia Trace - walk to Lake Sumter Landing, holiday rental in The Villages
Beautiful 3/2 Villa in Virginia Trace - walk to Lake Sumter Landing, holiday rental in The Villages
Beautiful 3/2 Villa in Virginia Trace - walk to Lake Sumter Landing, holiday rental in The Villages

Beautiful 3/2 Villa in Virginia Trace - walk to Lake Sumter Landing

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
More info
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Nicest Location & Fully Equipped Charming Home in the “Heart” of The Villages., holiday rental in The Villages
Nicest Location & Fully Equipped Charming Home in the “Heart” of The Villages., holiday rental in The Villages
Nicest Location & Fully Equipped Charming Home in the “Heart” of The Villages., holiday rental in The Villages

Nicest Location & Fully Equipped Charming Home in the “Heart” of The Villages.

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
More info
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Bright, airy, upscale. Golf cart. Minutes to Sumter Landing & Brownwood Squares, holiday rental in The Villages
Bright, airy, upscale. Golf cart. Minutes to Sumter Landing & Brownwood Squares, holiday rental in The Villages
Bright, airy, upscale. Golf cart. Minutes to Sumter Landing & Brownwood Squares, holiday rental in The Villages

Bright, airy, upscale. Golf cart. Minutes to Sumter Landing & Brownwood Squares

Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
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Locatied in the Village of Virginia Trace. Lake Sumter Landing!, holiday rental in The Villages
Locatied in the Village of Virginia Trace. Lake Sumter Landing!, holiday rental in The Villages
Locatied in the Village of Virginia Trace. Lake Sumter Landing!, holiday rental in The Villages

Locatied in the Village of Virginia Trace. Lake Sumter Landing!

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
More info
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Walk To Brownwood Paddock Square, Restaurants & Nightly Entertainment, holiday rental in The Villages
Walk To Brownwood Paddock Square, Restaurants & Nightly Entertainment, holiday rental in The Villages
Walk To Brownwood Paddock Square, Restaurants & Nightly Entertainment, holiday rental in The Villages

Walk To Brownwood Paddock Square, Restaurants & Nightly Entertainment

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
More info
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DOG Friendly-Our Village Gem *Closest Walk To Lake Sumter* Golf Cart (4 Seat), holiday rental in The Villages
DOG Friendly-Our Village Gem *Closest Walk To Lake Sumter* Golf Cart (4 Seat), holiday rental in The Villages
DOG Friendly-Our Village Gem *Closest Walk To Lake Sumter* Golf Cart (4 Seat), holiday rental in The Villages

DOG Friendly-Our Village Gem *Closest Walk To Lake Sumter* Golf Cart (4 Seat)

Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
More info
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Must See!! 2 Bedroom/2 Bath home w/golf cart.  Now Booking summer and fall 2017!, holiday rental in The Villages
Must See!! 2 Bedroom/2 Bath home w/golf cart.  Now Booking summer and fall 2017!, holiday rental in The Villages
Must See!! 2 Bedroom/2 Bath home w/golf cart.  Now Booking summer and fall 2017!, holiday rental in The Villages

Must See!! 2 Bedroom/2 Bath home w/golf cart. Now Booking summer and fall 2017!

Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
More info
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DOG Friendly-Our Village Gem-Very Popular Location, 4 seat golfcart, King Master, holiday rental in The Villages
DOG Friendly-Our Village Gem-Very Popular Location, 4 seat golfcart, King Master, holiday rental in The Villages
DOG Friendly-Our Village Gem-Very Popular Location, 4 seat golfcart, King Master, holiday rental in The Villages

DOG Friendly-Our Village Gem-Very Popular Location, 4 seat golfcart, King Master

Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Magnificent golf course view from the Private heated pool., holiday rental in The Villages
Magnificent golf course view from the Private heated pool., holiday rental in The Villages
Magnificent golf course view from the Private heated pool., holiday rental in The Villages

Magnificent golf course view from the Private heated pool.

Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
More info
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Located in the Village of Virginia Trace. Lake Sumter Landing, holiday rental in The Villages
Located in the Village of Virginia Trace. Lake Sumter Landing, holiday rental in The Villages
Located in the Village of Virginia Trace. Lake Sumter Landing, holiday rental in The Villages

Located in the Village of Virginia Trace. Lake Sumter Landing

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
More info
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Located in The Village of Virginia Trace. Lake Sumter Landing!

Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
More info
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Stunning Golf & Sunset View, REDUCED RATE 5 nights April 22-27, holiday rental in The Villages
Stunning Golf & Sunset View, REDUCED RATE 5 nights April 22-27, holiday rental in The Villages
Stunning Golf & Sunset View, REDUCED RATE 5 nights April 22-27, holiday rental in The Villages

Stunning Golf & Sunset View, REDUCED RATE 5 nights April 22-27

Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
More info
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New Charming 2/2 Villa in Creekside Landing adjacent to Lake Sumter Landing w/GC

Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
More info
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GREAT LOCATION. BETWEEN BROWNWOOD AND LAKE SUMTER. GAS GOLF CART INCLUDED., holiday rental in The Villages
GREAT LOCATION. BETWEEN BROWNWOOD AND LAKE SUMTER. GAS GOLF CART INCLUDED., holiday rental in The Villages
GREAT LOCATION. BETWEEN BROWNWOOD AND LAKE SUMTER. GAS GOLF CART INCLUDED., holiday rental in The Villages

GREAT LOCATION. BETWEEN BROWNWOOD AND LAKE SUMTER. GAS GOLF CART INCLUDED.

Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
More info
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2 BED/2BATH PLUS DEN  COURTYARD VILLA, holiday rental in The Villages
2 BED/2BATH PLUS DEN  COURTYARD VILLA, holiday rental in The Villages
2 BED/2BATH PLUS DEN  COURTYARD VILLA, holiday rental in The Villages

2 BED/2BATH PLUS DEN COURTYARD VILLA

Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
More info
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Dog Friendly,  ELEGANT + CART + *Location - 2 MIN cart ride* to Sumter Sq, POOLS, holiday rental in The Villages
Dog Friendly,  ELEGANT + CART + *Location - 2 MIN cart ride* to Sumter Sq, POOLS, holiday rental in The Villages
Dog Friendly,  ELEGANT + CART + *Location - 2 MIN cart ride* to Sumter Sq, POOLS, holiday rental in The Villages

Dog Friendly, ELEGANT + CART + *Location - 2 MIN cart ride* to Sumter Sq, POOLS

Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
More info
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Beautiful Villa in the Heart of Florida's Friendliest Active Adult Community, holiday rental in The Villages
Beautiful Villa in the Heart of Florida's Friendliest Active Adult Community, holiday rental in The Villages
Beautiful Villa in the Heart of Florida's Friendliest Active Adult Community, holiday rental in The Villages

Beautiful Villa in the Heart of Florida's Friendliest Active Adult Community

Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
More info
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Everything you need - 3/2 home,  4-seat golf car, and Resident Lifestyle passes, holiday rental in The Villages
Everything you need - 3/2 home,  4-seat golf car, and Resident Lifestyle passes, holiday rental in The Villages
Everything you need - 3/2 home,  4-seat golf car, and Resident Lifestyle passes, holiday rental in The Villages

Everything you need - 3/2 home, 4-seat golf car, and Resident Lifestyle passes

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
More info
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EXCELLENT WATERFRONT LOCATION!  Courtyard Villa Convenient to Brownwood Square!, holiday rental in The Villages
EXCELLENT WATERFRONT LOCATION!  Courtyard Villa Convenient to Brownwood Square!, holiday rental in The Villages
EXCELLENT WATERFRONT LOCATION!  Courtyard Villa Convenient to Brownwood Square!, holiday rental in The Villages

EXCELLENT WATERFRONT LOCATION! Courtyard Villa Convenient to Brownwood Square!

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
More info
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LOCATION + CHARM! 2BR/2BA/2 Kings w/Gas Cart in Village of Duval. REMODELED 2019, holiday rental in The Villages
LOCATION + CHARM! 2BR/2BA/2 Kings w/Gas Cart in Village of Duval. REMODELED 2019, holiday rental in The Villages
LOCATION + CHARM! 2BR/2BA/2 Kings w/Gas Cart in Village of Duval. REMODELED 2019, holiday rental in The Villages

LOCATION + CHARM! 2BR/2BA/2 Kings w/Gas Cart in Village of Duval. REMODELED 2019

Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
More info
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Patio Villa in Duval Village -  *** Gas Golf Cart INCLUDED ***, holiday rental in The Villages
Patio Villa in Duval Village -  *** Gas Golf Cart INCLUDED ***, holiday rental in The Villages
Patio Villa in Duval Village -  *** Gas Golf Cart INCLUDED ***, holiday rental in The Villages

Patio Villa in Duval Village - *** Gas Golf Cart INCLUDED ***

Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
More info
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Now available  March 14-21, 2021!! Also, Jan 1 -5  2022!!, holiday rental in The Villages
Now available  March 14-21, 2021!! Also, Jan 1 -5  2022!!, holiday rental in The Villages
Now available  March 14-21, 2021!! Also, Jan 1 -5  2022!!, holiday rental in The Villages

Now available March 14-21, 2021!! Also, Jan 1 -5 2022!!

Holiday Rental House
0 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
More info
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Private Pool & Golf Cart Presented By RE/MAX Premier Property Management, holiday rental in The Villages
Private Pool & Golf Cart Presented By RE/MAX Premier Property Management, holiday rental in The Villages
Private Pool & Golf Cart Presented By RE/MAX Premier Property Management, holiday rental in The Villages

Private Pool & Golf Cart Presented By RE/MAX Premier Property Management

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
More info
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Beautiful Villa Near Sumter Landing, Your Home Away From Home, holiday rental in The Villages
Beautiful Villa Near Sumter Landing, Your Home Away From Home, holiday rental in The Villages
Beautiful Villa Near Sumter Landing, Your Home Away From Home, holiday rental in The Villages

Beautiful Villa Near Sumter Landing, Your Home Away From Home

Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
More info
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Courtyard Villa With Gas Golf Cart at Phillips Villas in Village of Woodbury, holiday rental in The Villages
Courtyard Villa With Gas Golf Cart at Phillips Villas in Village of Woodbury, holiday rental in The Villages
Courtyard Villa With Gas Golf Cart at Phillips Villas in Village of Woodbury, holiday rental in The Villages

Courtyard Villa With Gas Golf Cart at Phillips Villas in Village of Woodbury

Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
More info
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Entire 3 Bedroom House in The Villages, holiday rental in The Villages
Entire 3 Bedroom House in The Villages, holiday rental in The Villages
Entire 3 Bedroom House in The Villages, holiday rental in The Villages

Entire 3 Bedroom House in The Villages

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
More info
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Upgraded Villa Surrounded by Golf Courses. Gas Golf Cart., holiday rental in The Villages
Upgraded Villa Surrounded by Golf Courses. Gas Golf Cart., holiday rental in The Villages
Upgraded Villa Surrounded by Golf Courses. Gas Golf Cart., holiday rental in The Villages

Upgraded Villa Surrounded by Golf Courses. Gas Golf Cart.

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
More info
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Vacation Home, Golf Cart, presented by RE/MAX Premier Property Management, holiday rental in The Villages
Vacation Home, Golf Cart, presented by RE/MAX Premier Property Management, holiday rental in The Villages
Vacation Home, Golf Cart, presented by RE/MAX Premier Property Management, holiday rental in The Villages

Vacation Home, Golf Cart, presented by RE/MAX Premier Property Management

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
More info
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Stunning Location with Water and Golf Views close to Spanish Springs, holiday rental in The Villages
Stunning Location with Water and Golf Views close to Spanish Springs, holiday rental in The Villages
Stunning Location with Water and Golf Views close to Spanish Springs, holiday rental in The Villages

Stunning Location with Water and Golf Views close to Spanish Springs

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
More info
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DOG Friendly, ELEGANT VILLA + CART, 1 min walk to POOL Very Popular LOCATION, holiday rental in The Villages
DOG Friendly, ELEGANT VILLA + CART, 1 min walk to POOL Very Popular LOCATION, holiday rental in The Villages
DOG Friendly, ELEGANT VILLA + CART, 1 min walk to POOL Very Popular LOCATION, holiday rental in The Villages

DOG Friendly, ELEGANT VILLA + CART, 1 min walk to POOL Very Popular LOCATION

Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
More info
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Winter is Coming!  NO Cleaning Fee!  NO Extra Guest Fee!  Free Golf Cart!, holiday rental in The Villages
Winter is Coming!  NO Cleaning Fee!  NO Extra Guest Fee!  Free Golf Cart!, holiday rental in The Villages
Winter is Coming!  NO Cleaning Fee!  NO Extra Guest Fee!  Free Golf Cart!, holiday rental in The Villages

Winter is Coming! NO Cleaning Fee! NO Extra Guest Fee! Free Golf Cart!

Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
More info
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COZY HOME BETWEEN LAKE SUMTER AND BROWNWOOD SQUARE!, holiday rental in The Villages
COZY HOME BETWEEN LAKE SUMTER AND BROWNWOOD SQUARE!, holiday rental in The Villages
COZY HOME BETWEEN LAKE SUMTER AND BROWNWOOD SQUARE!, holiday rental in The Villages

COZY HOME BETWEEN LAKE SUMTER AND BROWNWOOD SQUARE!

Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
More info
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Designer home in The Villages Hillsborough near Brownwood Town Center, holiday rental in The Villages
Designer home in The Villages Hillsborough near Brownwood Town Center, holiday rental in The Villages
Designer home in The Villages Hillsborough near Brownwood Town Center, holiday rental in The Villages

Designer home in The Villages Hillsborough near Brownwood Town Center

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
More info
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Due to cancellation now available April-  Golf Cart included, holiday rental in The Villages
Due to cancellation now available April-  Golf Cart included, holiday rental in The Villages
Due to cancellation now available April-  Golf Cart included, holiday rental in The Villages

Due to cancellation now available April- Golf Cart included

Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
More info
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GOLF CART BEAUTIFUL HOME PET FRIENDLY, holiday rental in The Villages
GOLF CART BEAUTIFUL HOME PET FRIENDLY, holiday rental in The Villages
GOLF CART BEAUTIFUL HOME PET FRIENDLY, holiday rental in The Villages

GOLF CART BEAUTIFUL HOME PET FRIENDLY

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
More info
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DOG FRIENDLY, Modern-Elegant Villa + CART, Best LOCATION next to Sumter Sq, holiday rental in The Villages
DOG FRIENDLY, Modern-Elegant Villa + CART, Best LOCATION next to Sumter Sq, holiday rental in The Villages
DOG FRIENDLY, Modern-Elegant Villa + CART, Best LOCATION next to Sumter Sq, holiday rental in The Villages

DOG FRIENDLY, Modern-Elegant Villa + CART, Best LOCATION next to Sumter Sq

Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
More info
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Private Pool, spa  w/Cart Presented By Re/MAX Premier Property Management, holiday rental in The Villages
Private Pool, spa  w/Cart Presented By Re/MAX Premier Property Management, holiday rental in The Villages
Private Pool, spa  w/Cart Presented By Re/MAX Premier Property Management, holiday rental in The Villages

Private Pool, spa w/Cart Presented By Re/MAX Premier Property Management

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
More info
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CLEAN & SANITIZED! Walk to Lake Sumter Landing from Gorgeous 3/2 Villa!, holiday rental in The Villages
CLEAN & SANITIZED! Walk to Lake Sumter Landing from Gorgeous 3/2 Villa!, holiday rental in The Villages
CLEAN & SANITIZED! Walk to Lake Sumter Landing from Gorgeous 3/2 Villa!, holiday rental in The Villages

CLEAN & SANITIZED! Walk to Lake Sumter Landing from Gorgeous 3/2 Villa!

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
More info
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Beautiful Home! Come enjoy The Villages, holiday rental in The Villages
Beautiful Home! Come enjoy The Villages, holiday rental in The Villages
Beautiful Home! Come enjoy The Villages, holiday rental in The Villages

Beautiful Home! Come enjoy The Villages

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
More info
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Immediate availability Feb 2021!  Call today!!, holiday rental in The Villages
Immediate availability Feb 2021!  Call today!!, holiday rental in The Villages
Immediate availability Feb 2021!  Call today!!, holiday rental in The Villages

Immediate availability Feb 2021! Call today!!

Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
More info
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Bright, Spacious and Beautiful!, holiday rental in The Villages
Bright, Spacious and Beautiful!, holiday rental in The Villages
Bright, Spacious and Beautiful!, holiday rental in The Villages

Bright, Spacious and Beautiful!

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
More info
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Everything you need - 3/2 home, 4-seat golf car, and Resident Lifestyle passes, holiday rental in The Villages
Everything you need - 3/2 home, 4-seat golf car, and Resident Lifestyle passes, holiday rental in The Villages
Everything you need - 3/2 home, 4-seat golf car, and Resident Lifestyle passes, holiday rental in The Villages

Everything you need - 3/2 home, 4-seat golf car, and Resident Lifestyle passes

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
More info
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Beautiful Pet Friendly 3/3 home with use of golf cart, holiday rental in The Villages
Beautiful Pet Friendly 3/3 home with use of golf cart, holiday rental in The Villages
Beautiful Pet Friendly 3/3 home with use of golf cart, holiday rental in The Villages

Beautiful Pet Friendly 3/3 home with use of golf cart

Holiday Rental House
3 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
More info
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Beautiful Home - 4 seat golf cart - WIFI - BBQ grill, holiday rental in The Villages
Beautiful Home - 4 seat golf cart - WIFI - BBQ grill, holiday rental in The Villages
Beautiful Home - 4 seat golf cart - WIFI - BBQ grill, holiday rental in The Villages

Beautiful Home - 4 seat golf cart - WIFI - BBQ grill

Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
More info
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Location, Location,Location, holiday rental in The Villages
Location, Location,Location, holiday rental in The Villages
Location, Location,Location, holiday rental in The Villages

Location, Location,Location

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
More info
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Welcome to Tee Off Villa - Beautiful 2 Bd/2 Ba on Golf Course w/Cart & Hot Tub, holiday rental in The Villages
Welcome to Tee Off Villa - Beautiful 2 Bd/2 Ba on Golf Course w/Cart & Hot Tub, holiday rental in The Villages
Welcome to Tee Off Villa - Beautiful 2 Bd/2 Ba on Golf Course w/Cart & Hot Tub, holiday rental in The Villages

Welcome to Tee Off Villa - Beautiful 2 Bd/2 Ba on Golf Course w/Cart & Hot Tub

Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 5
Match: Sleeps
More info
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Virginia Trace Villa, Walking Distance to Sumter Landing, Just Became Available, holiday rental in The Villages
Virginia Trace Villa, Walking Distance to Sumter Landing, Just Became Available, holiday rental in The Villages
Virginia Trace Villa, Walking Distance to Sumter Landing, Just Became Available, holiday rental in The Villages

Virginia Trace Villa, Walking Distance to Sumter Landing, Just Became Available

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
More info
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Marilyn’s Romantic Getaway, holiday rental in The Villages
Marilyn’s Romantic Getaway, holiday rental in The Villages
Marilyn’s Romantic Getaway, holiday rental in The Villages

Marilyn’s Romantic Getaway

Holiday Rental House
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
More info
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