Holiday Rentals in Rutland

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Holiday Rentals in Rutland

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

10.0 out of 10, Exceptional, (108)
"Great landlords, beautiful villa and great location "
Location! Our Village Gem-5 Star-3 min to Sumter Landing-Restaurants-Town Square

Modern Comfort & Prime Location in The Villages – Golf Cart Included!

10.0 out of 10, Exceptional, (70)
"We had a wonderful stay at this hidden gem in The Villages! The location was perfect — close to everything we needed — and having the golf cart was a huge bonus. The home was clean, cozy, and had everything we needed for a relaxing getaway. We would definitely stay again!"
Modern Comfort & Prime Location in The Villages – Golf Cart Included!

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

9.8 out of 10, Exceptional, (111)
"We had a great stay. Thank you! "
WOW.. ELEGANT Courtyard Villa, GOLF CART, Walk to Sumter Square & pool, sleep 6+

Perfect location! 3b2bFree golf cart! Minutes to Lake Sumter&Spanish Springs

9.6 out of 10, Exceptional, (70)
"The house fit our needs perfectly. It was very clean, in a nice, quiet neighborhood. The TV's were nice with many viewing options. It was close to Spanish Springs and Lake Sumter Landing town squares making it easy to get around. Definitely would recommend. "
Perfect location! 3b2bFree golf cart! Minutes to Lake Sumter&Spanish Springs

Perfect Getaway #2 Near Rainbow Springs and Withlacoochee Trail head

10.0 out of 10, Exceptional, (11)
"The property was very relaxing, comfortable and clean in a very quiet neighborhood close to everything but not on top of your neighbors. Will definitely be staying here again and highly recommend. "
The price is €289
includes taxes & fees
11 Sept - 12 Sept
Perfect Getaway #2 Near Rainbow Springs and Withlacoochee Trail head

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

5 Minute Golf Cart Ride To Brownwood, Restaurants, Entertainment

10.0 out of 10, Exceptional, (58)
"Great property; great location "
5 Minute Golf Cart Ride To Brownwood, Restaurants, Entertainment

Private Pool, Golf Cart, & Pet Friendly. Close to Golf and Town Squares.

8.8 out of 10, Excellent, (3)
"Great place in a very convenient location "
Private Pool, Golf Cart, & Pet Friendly. Close to Golf and Town Squares.

Vacation Home with luxurious pool in The Villages, Florida!

10.0 out of 10, Exceptional, (45)
"We had a great time enjoying the beautiful pool and outdoor barbeque area. The home was very comfortable for six adults. Jeff and Aggie were wonderful hosts and responded quickly to any questions we had. This is a beautiful home for a family get away."
The price is €566
includes taxes & fees
2 Sept - 3 Sept
Vacation Home with luxurious pool in The Villages, Florida!

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

10.0 out of 10, Exceptional, (49)
"The property is very well kept and Brad was very great to deal with"
FREE Golf Cart! Fabulous Location! Classy Decor! Pet-friendly!

Heated Pool house in Lake Panasoffkee

9.6 out of 10, Exceptional, (37)
"Great clean house, thanks for having us!"
The price is €303
includes taxes & fees
8 Sept - 9 Sept
Heated Pool house in Lake Panasoffkee

Golf Front Home, Solar Heat Pool! FREE golf cart, wifi, awesome view

10.0 out of 10, Exceptional, (215)
"We loved our stay! The house is spacious, well stocked, clean and great location. We enjoyed relaxing on the lanai with the beautiful view of the golf course and pool. David is an excellent host! "
Golf Front Home, Solar Heat Pool! FREE golf cart, wifi, awesome view

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.

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

Escape to Luxury: Designer Pool Home in Harmswood of Belle Aire, The Villages

2.5 star property
10.0 out of 10, Exceptional, (7)
"Was the perfect location for a big family gathering (some of our family were in the Villages, so this was so convienient)"
Escape to Luxury: Designer Pool Home in Harmswood of Belle Aire, The Villages

The Villages FL Community w/ Elec. Golf Cart. Restaurants, Shopping & Hospitals.

10.0 out of 10, Exceptional, (21)
"We were in town visiting family. The house met our needs and enjoyed the golf cart to explore the villages on our down time."
The price is €369
includes taxes & fees
29 Sept - 30 Sept
The Villages FL Community w/ Elec. Golf Cart. Restaurants, Shopping & Hospitals.

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

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

3 bed/ 2 bath house in The Villages! Pet friendly, pool, hot tub and internet!

7.6 out of 10, Good, (4)
"Our stay was very accommodating! Very clean property and kind host! "
3 bed/ 2 bath house in The Villages! Pet friendly, pool, hot tub and internet!

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
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 Rutland Hotel Reviews

Find out more about Rutland

Find out more about Rutland

Everything you need to know about Rutland holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Rutland holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, apart-hotels, cabins, villas... The list goes on, and on… and on!

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Rutland holiday rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search. 

Rutland holiday rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Rutland. If you’re looking for a little peace, consider booking during the quieter months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Rutland holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Rutland holiday rentals we have selected for you start as low as €289 per night. Entering your travel dates in the search wizard you might find even better deals!

How to find incredible deals on Rutland rentals

At Expedia, we put the best Rutland holiday rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia. 

To find some top Rutland rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Rutland holiday.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Rutland. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence. 

Frequently asked questions

Can I find holiday rentals in Rutland?

Yes, there are holiday rentals close to the most popular sights in Rutland, or you can select a more secluded option if you're looking for a relaxing stay.

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

Location! Our Village Gem-5 Star-3 min to Sumter Landing-Restaurants-Town Square: This holiday home rental outside of Rutland 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.

What’s there to see and do in Rutland?

Explore the area and family-friendly sights such as Don Garlits Museum of Racing, or get out into nature at a spot like Lake Okahumpka Park. In the wider area, you’ll find Citrus County Speedway and Lakeside Golf and Country Club.

What’s a holiday rental in Rutland like?

Holiday rentals are private properties where you can stay for a few weeks, or just a few days, in Rutland. Holiday rentals feature extras such as WiFi and washers and dryers so you'll have all the comforts of home. If you're concerned about a sanitised environment, holiday rentals can offer a sense of security away from public hotel lifts and busy concierge desks while still allowing you a great travel experience. You'll also find more space in a holiday rental than in a traditional hotel, which is another reason why a holiday rental is a popular choice for a family getaway.