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Top Holiday Rentals in The Villages

Our top choices for The Villages holiday rentals

Location! Our Village Gem-5 Star-3 min to Sumter Landing-Restaurants-Town Square

10.0 out of 10, Exceptional, (107)
"Great landlords, beautiful villa and great location "
Location! Our Village Gem-5 Star-3 min to Sumter Landing-Restaurants-Town Square

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

9.6 out of 10, Exceptional, (109)
"We had a great stay. Thank you! "
WOW.. ELEGANT Courtyard Villa, GOLF CART, Walk to Sumter Square & pool, sleep 6+

FREE Golf Cart! Fabulous Location! Classy Decor! Pet-friendly!

10.0 out of 10, Exceptional, (48)
"The property is very well kept and Brad was very great to deal with"
FREE Golf Cart! Fabulous Location! Classy Decor! Pet-friendly!

Our Village Gem-5 Star- Elegant & Comfortable- Very Close to Sumter Squ.

10.0 out of 10, Exceptional, (116)
"Everything was very nice, no issues at all."
Our Village Gem-5 Star- Elegant & Comfortable- Very Close to Sumter Squ.

Comfortable Cottage With A Golf Cart - NOT LISTED ON FACEBOOK

10.0 out of 10, Exceptional, (26)
"Great place to stay. Close to Lake Sumter and owner supplied all are needs. Do not hesitate to stay here you will be happy with the property. "
Comfortable Cottage With A Golf Cart - NOT LISTED ON FACEBOOK

Beautiful 3/2 Designer Home, WiFi, golf cart and 40 executive golf courses

9.6 out of 10, Exceptional, (69)
"Perfect accommodations. Thank you! Be back in the area in the fall. We'll definitely look this one up again."
Beautiful 3/2 Designer Home, WiFi, golf cart and 40 executive golf courses

Beautiful 3/2 designer home, pet friendly, free WiFi, golf cart, hot tub

9.0 out of 10, Wonderful, (68)
"Grear stay at a nice property. Unlike most rentals, the host provided basic food staples, condiments and coffee filters. It waa a nice touch!"
Beautiful 3/2 designer home, pet friendly, free WiFi, golf cart, hot tub

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

9.4 out of 10, Exceptional, (85)
"Good"
WOW...ELEGANT... Courtyard VILLA + Golf CART, Steps to POOL, 3 Min to Sumter SQ

Sunny Home in The Villages w/ Lanai & Pool Access!

7.4 out of 10, Good, (13)
"My day was amazing the house was very clean it was very well stocked with everything you could think of that you may need on a trip very comfortable home and a great location five star rating!!!!"
Sunny Home in The Villages w/ Lanai & Pool Access!

Private Heated Pool & Hottub - Pet Friendly- Close to L Sumpter & Spanish Spring

10.0 out of 10, Exceptional, (12)
"The home was accurately described in listing. Pool/Spa were hi light of our trip. Communication was excellent.Thank you Sue and Dave for a great vacation home rental."
Private Heated Pool & Hottub - Pet Friendly- Close to L Sumpter & Spanish Spring

Private Pool & Lake Views: Family Home in Oxford

8.8 out of 10, Excellent, (3)
"Great location. Visiting our parents in the Villages. Plenty of space for our family. Spacious rooms. Would rent again."
Private Pool & Lake Views: Family Home in Oxford

Piper's! On The Golf Course, Across From The Pool!

10.0 out of 10, Exceptional, (1)
"We visited The Villages for the first time with Mark & Bridget and they were nothing but kind and accommodating!! My friend and I drove golf carts for the first time and they were able to provide another one for our third person! We drove all over the place, enjoyed the square, ate so much, and danced the night away. We loved staying at their house and would love to come back!!!!! Thank you for everything!!! If we could give you 100 stars we would!!! "
Piper's! On The Golf Course, Across From The Pool!

Charming Oasis in The Villages - Pet-Friendly Paradise w/Golf Cart!

7.6 out of 10, Good, (12)
"It is a great location and very clean and comfortable house. We look forward to possibly returning to the house next year and possibly staying for a longer time."
Charming Oasis in The Villages - Pet-Friendly Paradise w/Golf Cart!

1 Mi to Pickleball & Golf: Home in The Villages

1 Mi to Pickleball & Golf: Home in The Villages

Single-story Home w/ Golf Cart in The Villages

3.0 star property
Single-story Home w/ Golf Cart in The Villages

Beautiful home on golf course w/ unheated lap pool! Dogs are ok!

9.6 out of 10, Exceptional, (14)
"Comfortable house in a great location."
Beautiful home on golf course w/ unheated lap pool! Dogs are ok!

Perfect Location Between Brownwood & Lake Sumter

9.8 out of 10, Exceptional, (106)
"Located close to all of our shopping needs."
Perfect Location Between Brownwood & Lake Sumter

The Coconut Courtayrd-Private Heated Saltwater Pool-Minutes From Fun-Walk 2 Golf

10.0 out of 10, Exceptional, (34)
"Enjoyed your beautiful home with family."
The price is £369
includes taxes & fees
25 Aug - 26 Aug
The Coconut Courtayrd-Private Heated Saltwater Pool-Minutes From Fun-Walk 2 Golf

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

10.0 out of 10, Exceptional, (116)
"Best VBRO that I have ever stayed at. "
Nicest Location & Fully Equipped Charming Home in the “Heart” of The Villages.

Jan 2026 Available! Beautiful 2 BR wGas Golf Cart in Duval. All 5 star reviews!

10.0 out of 10, Exceptional, (105)
"We had a great visit, as we did last year at the same property. Love the location and the house. It had everything we needed. Don and Lynn are wonderful hosts."
Jan 2026 Available! Beautiful 2 BR wGas Golf Cart in Duval. All 5 star reviews!
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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Top The Villages Hotel Reviews

Frequently asked questions

Can I find a holiday rental in The Villages?

Yes, there are holiday rentals close to the most popular sights in The Villages, or you can select a more secluded option if you're looking for a relaxing stay. Visitors like the top-notch restaurants and live music in The Villages. You can also check out the entertainment venues while you're visiting.

What are some of the best holiday rentals that The Villages has to offer?

Location! Our Village Gem-5 Star-3 min to Sumter Landing-Restaurants-Town Square: This highly rated holiday home rental in The Villages offers a patio, a garden and a BBQ to help you feel perfectly comfortable in your new surroundings. Kitchen amenities include a dishwasher, a fridge and a stovetop. Make the most of games in this rental home to help you unwind. Some other homes for rent in The Villages include The Villages FL Community w/ Elec. Golf Cart. Restaurants, Shopping & Hospitals. and Beautiful 3/2 designer home, pet friendly, free WiFi, golf cart, hot tub.

How many holiday rentals will I find in The Villages?

Expedia has 415 holiday rentals for your stay in The Villages.

What can I see and do in The Villages?

While exploring the area, visit family-friendly sights like Don Garlits Museum of Racing, or get outside and enjoy nature at Lake Weir. While here, The Villages Market Square and Nancy Lopez Legacy Golf & Country Club are other places worth a visit.

What are holiday rentals like in The Villages?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in The Villages. Holiday rentals provide amenities such as WiFi and washers and dryers so you'll have everything you want. If you're concerned about a clean environment, a holiday rental can offer a sense of seclusion away from shared hotel lifts and busy lobbies while still allowing you to travel. You'll also have more space in a holiday rental than in a standard hotel, which makes a holiday rental a popular choice for family trips.