Rutland Holiday Rentals

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Holiday Rentals in Rutland

Fully Furnished Brand New Villa in Village of St. Catherine's with Cart
10.0 out of 10, Exceptional, (65)
"Very nice and clean very close to all of the amenities that the villages offer"
Fully Furnished Brand New Villa in Village of St. Catherine's with Cart
BRAND NEW Dog Friendly 2/2 w. Golf Cart - Close to Activities, Shopping, Dining!
10.0 out of 10, Exceptional, (36)
"This was our first time visiting the villages. We loved our place and had a great time. There was some food left in the pantry, coffee and other little things that made it feel at home. We loved the squares. Brownwood square is close enough with golf cart but, I would take care for Sumter lake."
BRAND NEW Dog Friendly 2/2 w. Golf Cart - Close to Activities, Shopping, Dining!
Marilyn’s Romantic Getaway
10.0 out of 10, Exceptional, (42)
"My wife and l cannot say enough about the great experience we had on our 10 day visit at Marilyn’s. Owner Mark and his wife Tiffany were extremely accommodating and friendly. The house on Montoya street was very, very clean, comfortable and such a great location in Lady Lake between Sumpter Lake and Spanish Springs where shopping and Restaurants are easily accessible. You will ABSOLUTELY NOT BE disappointed in the whole experience. We will definitely return for other future visits. Manny and...
Marilyn’s Romantic Getaway
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Sparkling! Walking distance to Sumter Landing,pools & more,or take our golf cart
10.0 out of 10, Exceptional, (6)
"Very lovely house. Loved the golf cart, only used our SUV 4 times in the 2 wks we were there."
Sparkling! Walking distance to Sumter Landing,pools & more,or take our golf cart
Freshly Renovated Pool Home - Close to Crystal River - Spring Specials BOOK NOW!
10.0 out of 10, Exceptional, (40)
"Winderful property well maintained great accomodations well stocked property owner very responsive if something was needed"
Freshly Renovated Pool Home - Close to Crystal River - Spring Specials BOOK NOW!
1 mile from Nancy Lopez CC and Chatham Rec Centers.
9.6 out of 10, Exceptional, (13)
"The house and location are both excellent and highly recommended. Our only issue was the air conditioning. We did call on the first day but then it seemed to improve so we can canceled the service call. But it got hotter every day after that. Partly my bad, and I'm sure it's been addressed by now. So we recommend the property with no reservations. "
The price is NZ$357
includes taxes & fees
1 Jun - 2 Jun
1 mile from Nancy Lopez CC and Chatham Rec Centers.
New 3/2 Patio Villa, BEST VALUE, Golf Cart Included!
9.8 out of 10, Exceptional, (6)
"Awesome place to stay, would definitely stay again very clean and loved the garage for keeping the motorcycles in"
New 3/2 Patio Villa, BEST VALUE, Golf Cart Included!
Pool, Golf course view home with a golf cart
10.0 out of 10, Exceptional, (20)
"Perfect location convenient to golf, shopping and both sumpter landing square and spanish springs. Very high quality furnishings with attention to details. Linens were so comfortable and high quality ordered identical for home. Golf course view on patio with swim spa was just perfect. We hope to return"
Pool, Golf course view home with a golf cart
Walk To Brownwood Paddock Square, Restaurants & Nightly Entertainment
10.0 out of 10, Exceptional, (71)
"Adorable home, spotless and with all the amenities you need. The management company is also very responsive. Great location, too."
Walk To Brownwood Paddock Square, Restaurants & Nightly Entertainment
Amazing three-bedroom home in The Villages. Great spot for a memorable vacation!
10.0 out of 10, Exceptional, (44)
"A great place to gather. Nice space and well appointed. Reasonably priced. Thank you Robert for making the home welcoming and fun to stay. We had many laughs and took many good memories from The Villages."
The price is NZ$762
includes taxes & fees
1 Jul - 2 Jul
Amazing three-bedroom home in The Villages. Great spot for a memorable vacation!
BEAUTIFULLY Decorated 2/2 Sm Dog Friendly w/NEW GAS GOLF CART, BBQ & BICYCLES
9.6 out of 10, Exceptional, (10)
"This rental property was a great place to stay. Nicely located near activities."
BEAUTIFULLY Decorated 2/2 Sm Dog Friendly w/NEW GAS GOLF CART, BBQ & BICYCLES
Dog-friendly Summerfield home with a fenced-in yard, pool, hot tub, & games
10.0 out of 10, Exceptional, (7)
"Very nice house. Outdoor area and pool were wonderful. Loved the outdoor TV. Could use some more cooking dishware, but very minor issue. Would happily stay again."
Dog-friendly Summerfield home with a fenced-in yard, pool, hot tub, & games
Get Cozy in this newly renovated home by The Villages!
10.0 out of 10, Exceptional, (8)
"This house was VERY clean! Contact with property manager/owner was great! Adorable little neighborhood. Would definitely stay here again."
Get Cozy in this newly renovated home by The Villages!
Cozy Villages villa, 2 bed, 2 bath. Great Location
10.0 out of 10, Exceptional, (37)
"Really enjoyed staying here...."
Cozy Villages villa, 2 bed, 2 bath. Great Location
Casa Linda, Stunning Country Experience, Powered By Nature & Natural Sunlight.
4.8 out of 10, (3)
"Overall nice place and very nice host. Place could use some work and detailed cleaning. We saw evidence of past mice (droppings), but no current activity. We also saw a couple roaches (it is Florida), but the pest control sprayed while we were there. I would stay there again."
The price is NZ$343
includes taxes & fees
3 Jun - 4 Jun
Casa Linda, Stunning Country Experience, Powered By Nature & Natural Sunlight.
Luxurious Pool Home!
9.8 out of 10, Exceptional, (42)
"I felt the pictures on line did not do justice to the property in person!! Great house great pool…. Will stay there again if available for sure!!!!"
Luxurious Pool Home!
Come Enjoy The Golf Course View! This 2 bdrm Home Awaits You
9.0 out of 10, Wonderful, (2)
"Everything we wanted in a clean, comfortable, relaxing setting. Close to everything in the Villages in a quiet and serene neighborhood. Thank you! We will be back again."
Come Enjoy The Golf Course View! This 2 bdrm Home Awaits You
Hot Tub House - Entire 3 Bedroom House in The Villages
10.0 out of 10, Exceptional, (74)
"We enjoyed our stay. Check-in/Check-out was very easy with detailed instructions from the hosts. The house was very clean and comfortable and in a nice, quiet neighborhood close to Spanish Springs Square, golf courses, pools, restaurants and grocery stores. The hosts provided several kitchen staples such as coffee, spices, baggies, etc. as well as a few toiletries and beach towels which was very nice. Our guest passes were available upon arrival so we were all set to go enjoy The Villages on day...
Hot Tub House - Entire 3 Bedroom House in The Villages
Pet-Friendly Home w/ Lanai + Resort Amenities!
10.0 out of 10, Exceptional, (13)
"Great Location!"
Pet-Friendly Home w/ Lanai + Resort Amenities!
Fun of The Villages FL. 5 minutes to Spanish Springs. 10 Min to Sumter Landing.
Fun of The Villages FL. 5 minutes to Spanish Springs. 10 Min to Sumter Landing.
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See all available properties in Rutland
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.

Other types of properties in Rutland you may be interested in

Microtel Inn & Suites by Wyndham Ocala
2.0 star property
7.2 out of 10, Good, (1004)
"Lovely place to stay."
The price is NZ$126
includes taxes & fees
16 Jun - 17 Jun
Microtel Inn & Suites by Wyndham Ocala
The Waterfront Inn
3.0 star property
9.0 out of 10, Wonderful, (1004)
"Room was so clean, we had no allergy issues at all. The bed was one of the most comfortable beds we’ve ever slept on."
The price is NZ$226
includes taxes & fees
2 Jun - 3 Jun
The Waterfront Inn
Brownwood Hotel & Spa
3.0 star property
9.6 out of 10, Exceptional, (1008)
"We had a Fantastic room. The lounge was a great environment as well. "
The price is NZ$278
includes taxes & fees
2 Jun - 3 Jun
Brownwood Hotel & Spa
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.

You always said you would go on a dream holiday someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannonball into the deep end. Go ahead, unplug and unwind in style. When you book one of our Rutland holiday rentals, the ordinary is in the rearview. Instead of sharing your vacation with hundreds of hotel guests, you get to take advantage of all the space at your private apartment. You also get to enjoy all the amenities of a private residence for a truly unique and memorable stay. Why don’t you take off your shoes and settle in for a while? Your holiday just got upgraded.

As much as you love your vacation rental, it’s always good to get out and explore to soak up Rutland. Live like a local: Eat regional food, cheer on the home team, and visit the best cultural attractions in town. No matter the season, there is always something going on in Rutland. Seeing all the best attractions is bound to make you fall in love with Rutland. Who knows, you may even be tempted to extend your stay. There’s a reason home rentals are so popular here—after a long day of exploration, going back to your very own living room to stretch out is a dream come true. 

It’s your escape so why share it? You deserve your own slice of paradise. Booking your holiday rental on Expedia is simple and safe. Just pick your dates to search for the perfect property and book securely. We let you contact the property owner directly to make any special arrangements. All that’s left to do is show up with bells on and have a memorable vacation. With all the amenities available in Rutland short-term rentals, that won’t be hard to do.

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?

Marilyn’s Romantic Getaway: This holiday home rental outside of Rutland offers a fireplace, 1 hot tub and air conditioning to help you feel perfectly comfortable in your new surroundings. Kitchen amenities include a dishwasher, a fridge and a stovetop.

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 Fort Cooper State 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.

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