Rutland Vacation Rentals

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Vacation Rentals in Rutland

Our top choices for Rutland vacation rentals

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, (114)
"Nice and cleanGood location "
WOW.. ELEGANT Courtyard Villa, GOLF CART, Walk to Sumter Square & pool, sleep 6+

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

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

10.0 out of 10, Exceptional, (110)
"Great landlords, beautiful villa and great location "
Location! Our Village Gem-5 Star-3 min to Sumter Landing-Restaurants-Town Square

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

10.0 out of 10, Exceptional, (21)
"Great location and beautiful property! Had everything we needed. "
$396 nightly
The price is $420
Sep 26 - Sep 27
Total with taxes and fees
The Villages FL Community w/ Elec. Golf Cart. Restaurants, Shopping & Hospitals.

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

9.6 out of 10, Exceptional, (70)
"I enjoyed the stay!"
Perfect location! 3b2bFree golf cart! Minutes to Lake Sumter&Spanish Springs

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

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

9.4 out of 10, Exceptional, (86)
"Excellent experience. Property, location, and hosts were awesome. Highly recommended!"
WOW...ELEGANT... Courtyard VILLA + Golf CART, Steps to POOL, 3 Min to Sumter SQ

Lake View Retreat Loaded For Fun, with STUNNING Views!

10.0 out of 10, Exceptional, (36)
"Worked out well for golfing trip just a great place to stay and the host or excellent"
$686 nightly
The price is $752
Sep 15 - Sep 16
Total with taxes and fees
Lake View Retreat Loaded For Fun, with STUNNING Views!

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

10.0 out of 10, Exceptional, (216)
"Super location!"
Golf Front Home, Solar Heat Pool! FREE golf cart, wifi, awesome view

Hot Tub House - Entire 3 Bedroom House in The Villages

10.0 out of 10, Exceptional, (104)
"Great house, very clean. Easy check in and great communication!"
Hot Tub House - Entire 3 Bedroom House in The Villages

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

9.6 out of 10, Exceptional, (71)
"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

Vacation Home with luxurious pool in The Villages, Florida!

10.0 out of 10, Exceptional, (46)
"Fantastic property!This was one of the nicest VRBO's we have ever stayed it. The furnishings, linens, layout, furniture were top notch. It was stocked with everything we could possibly need or want in the kitchen, bedrooms, bathrooms, pool area, grill area. It was just as advertised, and Jeff was extremely easy to work with when we had questions. This is an awesome place."
$662 nightly
The price is $703
Sep 14 - Sep 15
Total with taxes and fees
Vacation Home with luxurious pool in The Villages, Florida!

5 Minute Golf Cart Ride To Brownwood, Restaurants, Entertainment

10.0 out of 10, Exceptional, (59)
"Great property; great location "
5 Minute Golf Cart Ride To Brownwood, Restaurants, Entertainment

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

9.0 out of 10, Wonderful, (68)
"Great location. Clean. Helpful host. Quiet area. "
Beautiful 3/2 designer home, pet friendly, free WiFi, golf cart, hot tub

Heated pool house with a canal access in Lake Panasoffkee

9.6 out of 10, Exceptional, (37)
"Great clean house, thanks for having us!"
$321 nightly
The price is $341
Sep 14 - Sep 15
Total with taxes and fees
Heated pool house with a canal access in Lake Panasoffkee

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!

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

Lake Front House with Covered Boat Dock, Great Fishing, Pets, internet, canoe

9.6 out of 10, Exceptional, (145)
"Old Florida"
Lake Front House with Covered Boat Dock, Great Fishing, Pets, internet, canoe

Pool, Golf Course View Home, 4 place golf cart

10.0 out of 10, Exceptional, (39)
"Such a wonderful place to stay and relax. The villa is beautiful. So clean and comfortable. Having breakfast outside every morning with the fantastic view. The hosts are amazing and we didnt want for anything. Very much look forward to going back next year."
Pool, Golf Course View Home, 4 place golf cart
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 vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Rutland vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. 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 vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Rutland vacation 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 low season months. For more hustle and bustle, you may prefer to visit Rutland in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $341 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

How to find incredible deals on Rutland rentals

At Expedia, we put the best Rutland vacation 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 vacation.

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 vacation rentals in Rutland?

Yes, there are vacation rentals close to the most popular attractions in Rutland, or you can select a secluded option if you'd like a relaxing place to stay.

What are some of the best vacation rentals in Rutland?

Modern Comfort & Prime Location in The Villages – Golf Cart Included!: Visitors like this Rutland vacation home rental. It offers a patio, a garden, and a barbecue grill to help you feel perfectly comfortable in your new surroundings. Kitchen amenities include a dishwasher, a fridge, and a stovetop. Make the most of the selection 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 larger area, you’ll find Citrus County Speedway and Lakeside Golf and Country Club.

What’s a vacation rental in Rutland like?

Vacation rentals are privately owned properties you can book for several days or longer in Rutland. Vacation rentals offer amenities such as kitchens and laundry facilities so you'll be comfy for your stay. If you're concerned about a clean environment, a vacation rental can offer a sense of seclusion away from public hotel elevators and busy reception areas while still allowing you the experience of travel. You'll also find more space in a vacation rental than in a traditional hotel, which is another reason why a vacation rental is an attractive choice for a small group gathering.