Rutland Vacation Rentals

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Check prices for these dates

Tonight
Dec 12 - Dec 13
Tomorrow
Dec 13 - Dec 14
This weekend
Dec 12 - Dec 14
Next weekend
Dec 19 - Dec 21

Our top choices for Rutland vacation rentals

Interior
Landing At Wildwood Near Lake Sumter Landing

Landing At Wildwood Near Lake Sumter Landing

Landing At Wildwood Near Lake Sumter Landing
4.0 star property
Oxford
9.6 out of 10, Exceptional, (4)
"Very clean and convenient check-in and check-out. "
United States
Laurie
Landing At Wildwood Near Lake Sumter Landing
Dining
Sunshine Stay a Creekside Villa at Lake Sumter Landing with Nature & Water Views

Sunshine Stay a Creekside Villa at Lake Sumter Landing with Nature & Water Views

Sunshine Stay a Creekside Villa at Lake Sumter Landing with Nature & Water Views
Lake Sumter Landing
10.0 out of 10, Exceptional, (1)
"Quick response from our host, great location, and the home was warm and welcoming. Very easy for my parents to get around in their wheelchair and walker "
United States
David T.
Sunshine Stay a Creekside Villa at Lake Sumter Landing with Nature & Water Views
Smart TV, stereo
Comfortable Cottage With A Golf Cart - NOT LISTED ON FACEBOOK

Comfortable Cottage With A Golf Cart - NOT LISTED ON FACEBOOK

Comfortable Cottage With A Golf Cart - NOT LISTED ON FACEBOOK
Lynnhaven
10.0 out of 10, Exceptional, (29)
"Clean and comfortable. Everything we needed was there and communication was easy! Highly recommend if you need a place to stay b"
United States
Brianna J.
Comfortable Cottage With A Golf Cart - NOT LISTED ON FACEBOOK
Interior
Private heated in-ground pool oasis with golf cart in Rio Grande!

Private heated in-ground pool oasis with golf cart in Rio Grande!

Private heated in-ground pool oasis with golf cart in Rio Grande!
The Villages
10.0 out of 10, Exceptional, (3)
"Nice house. Pool is nice and warm and deep! Host was very quick to respond to any questions we had."
United States
Lisa H.
Private heated in-ground pool oasis with golf cart in Rio Grande!
Fridge, microwave, oven, stovetop
BETTER THAN A 5 STAR HOTEL WITH GOLF CART WHOLE HOUSE TOTALLY REMODELED

BETTER THAN A 5 STAR HOTEL WITH GOLF CART WHOLE HOUSE TOTALLY REMODELED

BETTER THAN A 5 STAR HOTEL WITH GOLF CART WHOLE HOUSE TOTALLY REMODELED
Alhambra
10.0 out of 10, Exceptional, (9)
The price is ￥12,284
￥38,450 total
includes taxes & fees
Dec 15 - Dec 16
BETTER THAN A 5 STAR HOTEL WITH GOLF CART WHOLE HOUSE TOTALLY REMODELED
Terrace/patio
Newly Renovated 2BR/2BA + Golf Cart, WiFi & Streaming!

Newly Renovated 2BR/2BA + Golf Cart, WiFi & Streaming!

Newly Renovated 2BR/2BA + Golf Cart, WiFi & Streaming!
2.5 star property
Sanibel
10.0 out of 10, Exceptional, (3)
"A beautiful home and very responsive hosts. The inside was so clean and well decorated, with welcome touches like soft lap blankets on the couch, a first aid kit, storage containers for our leftovers, and even a freezer compress for my sore knee after tennis and golf! We hope to be back again!"
United States
B H.
Newly Renovated 2BR/2BA + Golf Cart, WiFi & Streaming!
Interior
Modern Comfort & Prime Location in The Villages – Golf Cart Included!

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

Modern Comfort & Prime Location in The Villages – Golf Cart Included!
Santo Domingo
10.0 out of 10, Exceptional, (81)
"Beautifully decorated, clean, and comfortable!"
United States
Robin W.
Modern Comfort & Prime Location in The Villages – Golf Cart Included!
Exterior
The Villages FL Community w/ Elec. Golf Cart. Restaurants, Shopping & Hospitals.

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

The Villages FL Community w/ Elec. Golf Cart. Restaurants, Shopping & Hospitals.
Sanibel
10.0 out of 10, Exceptional, (26)
"Great location and beautiful property! Had everything we needed. "
United States
Amber L.
The Villages FL Community w/ Elec. Golf Cart. Restaurants, Shopping & Hospitals.
A heated pool
Golf Front Home, Solar Heat Pool! FREE golf cart, wifi, awesome view

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

Golf Front Home, Solar Heat Pool! FREE golf cart, wifi, awesome view
Collier
10.0 out of 10, Exceptional, (219)
"We had a great time enjoying our stay in the Villages."
United States
Bill K.
Golf Front Home, Solar Heat Pool! FREE golf cart, wifi, awesome view
Dining
Beautiful view, The Villages- Golf Front Home, Heated Pool, Free Golf Cart, WIFI

Beautiful view, The Villages- Golf Front Home, Heated Pool, Free Golf Cart, WIFI

Beautiful view, The Villages- Golf Front Home, Heated Pool, Free Golf Cart, WIFI
The Villages
10.0 out of 10, Exceptional, (99)
"Jenn the host of this property was excellent. We asked for early check-in and she was great. Pool was excellent. Overall the property was top shelf. Would highly recommend. "
United States
Wayne C.
Beautiful view, The Villages- Golf Front Home, Heated Pool, Free Golf Cart, WIFI
Dining
Welcome Small DOGS.. ELEGANT Villa, GOLF CART, Walk to Sumter Square, sleep 6

Welcome Small DOGS.. ELEGANT Villa, GOLF CART, Walk to Sumter Square, sleep 6

Welcome Small DOGS.. ELEGANT Villa, GOLF CART, Walk to Sumter Square, sleep 6
Virginia Trace
9.6 out of 10, Exceptional, (119)
"Was wonderful, great location, great owners, great house and great time. "
United States
Susie C.
Welcome Small DOGS.. ELEGANT Villa, GOLF CART, Walk to Sumter Square, sleep 6
TV
Courtyard Villa with gas golf cart located between two Town Squares!

Courtyard Villa with gas golf cart located between two Town Squares!

Courtyard Villa with gas golf cart located between two Town Squares!
The Villages
9.8 out of 10, Exceptional, (30)
" Very nice. Hosts were wonderful. Would love to return some day."
United States
Barbara K.
Courtyard Villa with gas golf cart located between two Town Squares!
Pool
Hot Tub House - Entire 3 Bedroom House in The Villages

Hot Tub House - Entire 3 Bedroom House in The Villages

Hot Tub House - Entire 3 Bedroom House in The Villages
Santo Domingo
10.0 out of 10, Exceptional, (106)
"Very nice stay, great home and location!"
United States
Tracy W.
Hot Tub House - Entire 3 Bedroom House in The Villages
Interior
3 bed/ 2 bath house in The Villages! Pet friendly, pool, hot tub and internet!

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

3 bed/ 2 bath house in The Villages! Pet friendly, pool, hot tub and internet!
Wildwood
7.6 out of 10, Good, (4)
"Our stay was very accommodating! Very clean property and kind host! "
United States
Kellie G.
3 bed/ 2 bath house in The Villages! Pet friendly, pool, hot tub and internet!
Exterior
Beautiful 3/2 Designer Home, WiFi, golf cart and 40 executive golf courses

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

Beautiful 3/2 Designer Home, WiFi, golf cart and 40 executive golf courses
Glenbrook
9.6 out of 10, Exceptional, (74)
"Great property and location was great for us"
United States
Greg B.
Beautiful 3/2 Designer Home, WiFi, golf cart and 40 executive golf courses
Exterior
Village of Fernandina - free use of golf cart with liability waiver

Village of Fernandina - free use of golf cart with liability waiver

Village of Fernandina - free use of golf cart with liability waiver
Fernandina
10.0 out of 10, Exceptional, (23)
"Check in & out was very convenient. The villa was very clean & met all my expectations. I will definitely consider renting again for next year."
United States
Corina S.
Village of Fernandina - free use of golf cart with liability waiver
Dining
Nicest Location & Fully Equipped Charming Home in the “Heart” of The Villages.

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

Nicest Location & Fully Equipped Charming Home in the “Heart” of The Villages.
Mallory Square
10.0 out of 10, Exceptional, (120)
"Outstanding location and a beautiful home that is spotless. Highly recommend this home"
United States
Rigo T.
Nicest Location & Fully Equipped Charming Home in the “Heart” of The Villages.
Interior
3 bedroom villa in The Villages. Minutes from Brownwood and Sawgrass.

3 bedroom villa in The Villages. Minutes from Brownwood and Sawgrass.

3 bedroom villa in The Villages. Minutes from Brownwood and Sawgrass.
The Villages
10.0 out of 10, Exceptional, (1)
"Great location. Enjoyed the stay and house was very clean with all needed amenities. "
United States
Kathleen W.
3 bedroom villa in The Villages. Minutes from Brownwood and Sawgrass.
Fridge, microwave, oven, stovetop
Christmas! Walk to Lake Sumter Landing! Our Village Gem - 5 Star - w/ Golf Cart

Christmas! Walk to Lake Sumter Landing! Our Village Gem - 5 Star - w/ Golf Cart

Christmas! Walk to Lake Sumter Landing! Our Village Gem - 5 Star - w/ Golf Cart
Caroline
10.0 out of 10, Exceptional, (117)
"Very nice property…Enjoyed my stay, thank you "
United States
Dennis P.
Christmas! Walk to Lake Sumter Landing! Our Village Gem - 5 Star - w/ Golf Cart
Dining
VILLA 2 MASTER SUITES & 2 GOLF CARTS

VILLA 2 MASTER SUITES & 2 GOLF CARTS

VILLA 2 MASTER SUITES & 2 GOLF CARTS
The Villages
10.0 out of 10, Exceptional, (77)
"Beautiful villa, the owners were amazing to deal with. I would love to stay there again."
United States
DEBBIE K.
VILLA 2 MASTER SUITES & 2 GOLF CARTS
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

Holiday Inn Express & Suites Wildwood The Villages by IHG

Holiday Inn Express & Suites Wildwood The Villages by IHG

10/10 Excellent
"Beds were fantastic, breakfast bountiful, everything perfect. We were very impressed with how well everything was done for us to have a great stay."
Mark 3-night trip
Posted 1 day ago
Holiday Inn Express & Suites Wildwood The Villages by IHG

Find out more about Rutland

Search for holiday rentals in Rutland on Expedia! You can easily find your home rentals, villas, holiday apartments in Rutland using one of the methods below:

  • View our selection of featured holiday rentals in Rutland
  • Use the map to find apartments and other holiday homes in the Rutland neighbourhood you prefer
  • Enter your travel dates to view the best deals on holiday rentals in Rutland while they last

Look no further and take a look at our great range of rental properties in Rutland!

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?

BETTER THAN A 5 STAR HOTEL WITH GOLF CART WHOLE HOUSE TOTALLY REMODELED: Visitors like this Rutland vacation home rental. It offers an outdoor pool, a patio, and a barbecue grill 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 Lake Okahumpka Park. In the larger area, you’ll find Half Moon Wildlife Management Area and Citrus County Speedway.

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.