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Check prices for these dates

Next weekend
2 Jum. I - 4 Jum. I
In two weeks
9 Jum. I - 11 Jum. I
In one month
23 Jum. I - 25 Jum. I
In two months
20 Jum. II - 22 Jum. II

Compare 261 Villas in Webster with updated reviews, rates, and availability.

Fully Furnished Brand New Villa in Village of St. Catherine's with Cart
Exterior

Fully Furnished Brand New Villa in Village of St. Catherine's with Cart

10.0 out of 10, Exceptional, (91)
"We have visited The Villages every March for the past 4 years. We’ve stayed in various homes in various “Villages” and this location and home has been our favorite. Wonderful location, lovely home and extremely efficient host. We booked this home again for March 2026, as soon as we unpacked for this year’s stay. "
Fully Furnished Brand New Villa in Village of St. Catherine's with Cart
Orlando Area 4 BR/3 BA Villa - Pool, Spa, Game Room, Wi-Fi, Gated Community
Exterior

Orlando Area 4 BR/3 BA Villa - Pool, Spa, Game Room, Wi-Fi, Gated Community

10.0 out of 10, Exceptional, (121)
"This house is in a great location just on the edge of Orlando in a quiet, secure neighborhood. It was easy to get in and out of and just a short trip to stores and restaurants. The house had everything we needed. The pool and hot tub were perfect for our family. It was very clean and comfortable and truly felt like a home away from home. We needed to reach out to the owner for a minor thing and she responded almost immediately to help us figure things out. We loved our stay here and would...
Orlando Area 4 BR/3 BA Villa - Pool, Spa, Game Room, Wi-Fi, Gated Community
Private 5 Bedroom Villa Near Disney, free WI-FI 10% OFF LONG TERM RENTALS
A heated pool

Private 5 Bedroom Villa Near Disney, free WI-FI 10% OFF LONG TERM RENTALS

9.4 out of 10, Exceptional, (126)
"Fantastic large property with everything needed for a week stay. We traveled to Orlando to go to Disney and this place was everything we needed and more. Was so nice to spread out and the kids all had their own room and bathroom which was amazing after spending a few weeks in hotel rooms. The pool was an added bonus. Property was clean and comfortable. Would recommend to anyone "
Private 5 Bedroom Villa Near Disney, free WI-FI 10% OFF LONG TERM RENTALS
NEW - Luxury decorated villa with amazing view, private pool and spa
Exterior

NEW - Luxury decorated villa with amazing view, private pool and spa

10.0 out of 10, Exceptional, (244)
"We weren't at the house much but enjoyed the quiet neighborhood"
NEW - Luxury decorated villa with amazing view, private pool and spa
Charming 3 Bedroom, 2 Bath Courtyard Villa in The Villages, FL
Exterior

Charming 3 Bedroom, 2 Bath Courtyard Villa in The Villages, FL

2.0 star property
10.0 out of 10, Exceptional, (14)
"We love the Villages and all they offer. The home was immaculate and nicely appointed we had everything we need and then some. Would definitely recommend!!"
The price is SAR 503
SAR 1,521 total
includes taxes & fees
19 May - 20 May
Charming 3 Bedroom, 2 Bath Courtyard Villa in The Villages, FL
Hidden Waterfront Oasis - 18 minutes to the Disney Entrance!
Outdoor pool, a heated pool

Hidden Waterfront Oasis - 18 minutes to the Disney Entrance!

10.0 out of 10, Exceptional, (86)
"House is beautiful from top to bottom. Neighborhood was quiet and friendly. You can watch the Florida wildlife from the backyard. Not to far from Disney but also not that close. Perfect house if not really interested in parks!"
Hidden Waterfront Oasis - 18 minutes to the Disney Entrance!
WOW.. ELEGANT Courtyard Villa, GOLF CART, Walk to Sumter Square & pool, sleep 6+
Fridge, microwave, oven, stovetop

WOW.. ELEGANT Courtyard Villa, GOLF CART, Walk to Sumter Square & pool, sleep 6+

9.8 out of 10, Exceptional, (99)
"Nice place. Nicely decorated.Couple of problems that were taken care of right away.Some screens in need of repairs to keep bugs out.Carpet needs a good cleaning"
WOW.. ELEGANT Courtyard Villa, GOLF CART, Walk to Sumter Square & pool, sleep 6+
Water View 2 Bedroom Villa centrally located in The Village of Marsh Bend
Interior

Water View 2 Bedroom Villa centrally located in The Village of Marsh Bend

10.0 out of 10, Exceptional, (9)
"Our first time renting a VRBO and everything was awesome. The owners were very communicative and a pleasure to rent from. We can't wait to come back to this amazing property!!"
Water View 2 Bedroom Villa centrally located in The Village of Marsh Bend
SUNSET COVE - Enjoy warm Florida sunsets in the Village of St Johns!
Smart TV

SUNSET COVE - Enjoy warm Florida sunsets in the Village of St Johns!

10.0 out of 10, Exceptional, (33)
"Very nice house and very clean. A few suggestions of the owner would be (i) you need a TV in master bedroom and (ii) upgrade the towels. "
The price is SAR 398
SAR 1,393 total
includes taxes & fees
18 May - 19 May
SUNSET COVE - Enjoy warm Florida sunsets in the Village of St Johns!
Stunning 2/2 Villa in Creekside Landing adjacent to Lake Sumter Landing w/Cart
Fridge, microwave, oven, stovetop

Stunning 2/2 Villa in Creekside Landing adjacent to Lake Sumter Landing w/Cart

10.0 out of 10, Exceptional, (65)
"We really enjoyed our short stay here in The Villages. You cannot beat the access to Sumtner Landing, which you can easily walk, bike (two bikes available), drive, or our favorite, the very awesome golf cart that comes with the rental. Golf cart seats four and held a long charge for us. Plenty of kitchenware, linens, towels and very clean and tidy. Would definitely stay again!"
Stunning 2/2 Villa in Creekside Landing adjacent to Lake Sumter Landing w/Cart
Bob's place
Fridge, microwave, oven, stovetop

Bob's place

10.0 out of 10, Exceptional, (1)
"Bob is a very friendly, approachable and accommodating host. He's flexible and easy to reach. The home was comfortable and equipped with everything I needed. I woukd definitely stay here again!"
Bob's place
Charming 2-Bedroom Courtyard Villa in The Villages
Fridge, microwave, oven, stovetop

Charming 2-Bedroom Courtyard Villa in The Villages

10.0 out of 10, Exceptional, (3)
"Everything was as expected. A very nice rental!"
Charming 2-Bedroom Courtyard Villa in The Villages
12 Miles to Disney: Clermont Villa w/ Heated Pool
Fridge, microwave, stovetop, dishwasher

12 Miles to Disney: Clermont Villa w/ Heated Pool

9.8 out of 10, Exceptional, (29)
"Came down for a family vacation the house was in the perfect spot away from any choas was peaceful neighborhood "
12 Miles to Disney: Clermont Villa w/ Heated Pool
King-Sized Comfort – 2 King Beds in a Serene "Hideaway" in The Villages
Living area

King-Sized Comfort – 2 King Beds in a Serene "Hideaway" in The Villages

9.6 out of 10, Exceptional, (10)
"Very professional house, clean and open. We enjoyed this property we will return"
The price is SAR 454
SAR 1,454 total
includes taxes & fees
13 May - 14 May
King-Sized Comfort – 2 King Beds in a Serene "Hideaway" in The Villages
Pick me! Pick me! 3/2, FREE golf & 4-seat cart, Resident passes, pets.
Smart TV, books, computer monitors, printers

Pick me! Pick me! 3/2, FREE golf & 4-seat cart, Resident passes, pets.

10.0 out of 10, Exceptional, (19)
"The Property was very clean, convenient and comfortable. Host was very kind and helpful."
Pick me! Pick me! 3/2, FREE golf & 4-seat cart, Resident passes, pets.
Most desirable location in The Villages With 4-Person Golf Cart, Caroline!
Fridge, microwave, oven, stovetop

Most desirable location in The Villages With 4-Person Golf Cart, Caroline!

10.0 out of 10, Exceptional, (25)
"This place was comfortable and clean. My family of 4 adults and 1 three year old enjoyed our stay! The directions for check in and check out were easy to follow,"
Most desirable location in The Villages With 4-Person Golf Cart, Caroline!
Perfect Location Between Brownwood & Lake Sumter
Fridge, microwave, oven, stovetop

Perfect Location Between Brownwood & Lake Sumter

10.0 out of 10, Exceptional, (101)
"Located close to all of our shopping needs."
Perfect Location Between Brownwood & Lake Sumter
Villages Winter Sunset View Private Patio Villa, Golf Cart, Brownwood
Exterior

Villages Winter Sunset View Private Patio Villa, Golf Cart, Brownwood

10.0 out of 10, Exceptional, (2)
"Our month stay was phenomenal because of the view complete with sand hill cranes, bluebirds and melodious mocking birds, lush tropical plantings on the private back patio with a sunsetter awning beautifully decorated home with IKEA , well appointed kitchen with a convection stove . Our owner insured our arrival and departure was seamless . The walking trail is a short skip away winding around the golf course, meeting up at marsh bend then water lily and back to our street entrance . The gas...
Villages Winter Sunset View Private Patio Villa, Golf Cart, Brownwood
Sparkling! Walking distance to Sumter Landing,pools & more,or take our golf cart
Fridge, microwave, oven, stovetop

Sparkling! Walking distance to Sumter Landing,pools & more,or take our golf cart

10.0 out of 10, Exceptional, (14)
"We had a great stay at this home. The owners were so wonderful to work with. Home is in a perfect location. It was well equipped, we had everything we needed. Every detail, large or small, was thought of by the owners. A wonderful experience."
Sparkling! Walking distance to Sumter Landing,pools & more,or take our golf cart
WOW...ELEGANT... Courtyard VILLA + Golf CART, Steps to POOL, 3 Min to Sumter SQ
A heated pool

WOW...ELEGANT... Courtyard VILLA + Golf CART, Steps to POOL, 3 Min to Sumter SQ

9.4 out of 10, Exceptional, (78)
"Nice community. Enjoyed nice restaurants, golf and weather. Thanks for the use of golf car. Property was clean and convenient to everything."
WOW...ELEGANT... Courtyard VILLA + Golf CART, Steps to POOL, 3 Min to Sumter SQ
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Other property types in Webster

Siena at Bella Collina
Front of property - evening/night

Siena at Bella Collina

3.5 star property
9.8 out of 10, Exceptional, (64)
"It’s nice and beautiful place."
The price is SAR 1,271
SAR 1,411 total
includes taxes & fees
18 May - 19 May
Siena at Bella Collina
Village of Mallory, Close to Sumter Landing Sq. 3BD, 2Bath with Gas Golf Cart.
Terrace/patio

Village of Mallory, Close to Sumter Landing Sq. 3BD, 2Bath with Gas Golf Cart.

9.2 out of 10, Wonderful, (46)
"We had a great time again. Looking forward to next year"
Village of Mallory, Close to Sumter Landing Sq. 3BD, 2Bath with Gas Golf Cart.
Paradise! 3br/3ba large Townhouse near the Epperson Lagoon Community
Pool

Paradise! 3br/3ba large Townhouse near the Epperson Lagoon Community

10.0 out of 10, Exceptional, (42)
"Beautiful home, beautiful neighborhood. Yvonne was a great host. "
The price is SAR 638
SAR 1,705 total
includes taxes & fees
7 May - 8 May
Paradise! 3br/3ba large Townhouse near the Epperson Lagoon Community
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

Frequently asked questions

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