Vacation rentals in Rutland

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Top-rated vacation rentals in Rutland

Guests agree: these stays are highly rated for location, cleanliness, and more.

Guest favorite

Townhouse in Kissimmee

4.8 out of 5 average rating, 246 reviews

#5708 LakeFront, Two Master, Jacuzzi, Pool, Disney

Stunning LAKEFRONT view with SOUTH exposure for all day SUNLIGHT. MODERN furniture & HARDWOOD floors! Private JACCUZI! 5 SMART TVs & FREE WIFI. 4 BDS (2 with ensuite, one on each floor) & 3.5 BATH. SS appliances, water filter and quartz counter tops. 10 mins to Disney, 15 mins to Sea World, 20 mins to Universal. Walk to Old Town, Fun Spot, restaurants and stores. Uber/Lyft/Lynx bus to Disney. Resort heated pool, water slides, fitness, tennis, restaurant/bar, mini store and 24/7 gate with guard.

Superhost

Home in Ocklawaha

5 out of 5 average rating, 4 reviews

As good as it gets! Lakefront - with a pool!

This 2/1 house sits directly on a large private beach with a massive enclosed pool area including an outdoor kitchen, smart TV and lots of space to relax. This is our family vacation home, so everything is there to ensure an amazing stay. A new two story dock offers spots to moor a boat or jet skis, and lots of sun and fun space: paddle boards, fire pit, picnic table, etc. A separate cottage is just behind it. Find it listed under my profile. Rent both together for a big family gathering!

Superhost

Home in Kissimmee

4.69 out of 5 average rating, 16 reviews

Cozy VacationHome - Disney Parks

Have fun with the whole family at this comfortable and spacious townhome, take advantage of the full amenities that come with it. This space is great for both short and long stays and excellent for family visits. Close to Disney & more Orlando Areas *18 min or 11 miles to Disney Area *26 min or 17 miles to SeaWorld *30 min or 21 miles to Universal *40 min or 34 miles to MCO International Airport Orlando *50 min or 29 miles to Legoland *1h 15 min to Tampa Beach *1h 30 min to Melbourne Beach

Guest favorite

Villa in Kissimmee

4.81 out of 5 average rating, 63 reviews

Home w/ PVT Pool, Game Room & Resort access 2100

Our luxurious 5-bedroom, 5.5-bathroom home boasts a spacious living room with Smart TV, a fully-equipped kitchen and dining room, a cozy upstairs living area perfect for movie nights as well as an air-conditioned game room featuring a pool table and air hockey. Venture to the backyard to find even more amazing features such as a spacious private pool and SPA, sun loungers, a barbecue and a table with 6 seats where you and your guests will be able to enjoy some sun-filled al fresco dining.

Guest favorite

Condo in Kissimmee

4.95 out of 5 average rating, 155 reviews

*Sunset Perch: Views, Reunion Resort, XBox, 2Pools

This modern 3-bedroom luxury condo (with an ELEVATOR right to the door) has one of the most PICTURESQUE VIEWS in the Reunion Resort of the Arnold Palmer PGA golf course. Combining STYLISH DESIGN and LUXURIOUS COMFORT, there are 2 KING bedrooms and a playful STAR WARS themed bedroom with a classic Arcade machine & Xbox. 4 TVs with DirecTV, free high-speed wifi, your own washer & dryer, access to 6 resort pools, 2 of which are only a 3 minute walk away, and only a short drive to Disney.

Guest favorite

Home in The Villages

4.88 out of 5 average rating, 25 reviews

Entire Home in The Villages Absolutely Beautiful!!

Neighborhood Pool, WIFI, Free Parking, Backyard View Excellent location, 2 bed 2 bath open floor plan home that borders a nature preserve looking out the lanai in the Village of Palo Alto. Walking distance to Spanish Springs and close to Lake Sumter Landing. Enjoy area amenities including pools, golf courses, tennis, pickle ball, shuffleboard and live entertainment every night of the week in three different locations. I do not live there. Prices include golf cart!

Guest favorite

Townhouse in Kissimmee

4.94 out of 5 average rating, 185 reviews

Beautiful family home near all attractions.

Beautiful, spacious and impeccable townhome close to all parks and entertainment with resort amenities. We follow Airbnb's enhanced cleaning protocol, which was developed with expert guidance. Here are a few highlights: *We sanitize high-touch surfaces, down to the doorknob. *We use cleaners and disinfectanst approved by global health agencies, and We wear protective gear to help prevent cross-contamination. *We clean each room using extensive cleaning checklist.

Guest favorite

Home in The Villages

5 out of 5 average rating, 15 reviews

New Village House Paradise! 30% weekly discounts!

☑ New King and Queen bed suites! ☑ Brand new appliances package! ☑ 55" LED Roku TV's in All Bedrooms ☑ 65" LED Roku TV with Sony Sound bar system and Subwoofer ☑ Upgraded Outlets (No charging blocks needed) Perfect location and perfect upgrades makes this home a great vacation destination. Home has fully stocked essentials for entertaining, Day at the Beach, grilling, everyday cooking, and baking. Note: Highly recommend golf cart rental (Not included).

Guest favorite

Home in Crescent City

5 out of 5 average rating, 15 reviews

Lake Cabin! Private Dock, Tennis Court & Pool

Cozy waterfront cabin! This log cabin located in Crescent City, FL has something for everyone! Master downstairs with king bed, 2 oversized bedrooms upstairs with king, queen, full, & 3 twins Game room, private pool, hot tub, private tennis court, basketball, corn hole & fishing! Pet-friendly with approval Cameras on property 1 Camera located in driveway 1 Ring doorbell on front door. FIREPLACE NOT AVAILABLE FOR USE DURING SPRING & SUMMER

Guest favorite

Guest suite in Port Richey

4.85 out of 5 average rating, 34 reviews

Cozy beautiful Rental

Our cozy vacation rental has a private entry fully gated with one queen bed, and if needed & requested i have a small toddler bed and a personal bed. Small separate kitchen with (small gas stove, microwave, coffee maker, Rice maker, frying pan, small dining table ). Private Bathroom and Parking for one car. Maximum 3 guests on property at a time, smoking only allowed outside in the patio area. stores 10min o less

Guest favorite

Townhouse in Kissimmee

4.88 out of 5 average rating, 34 reviews

Amazing Premium 4 Bedr 5* Resort unit Near Disney

Newly renovated upscale 4 bedroom townhouse, Located in a gated 24 hour guarded Resort, only 4 miles from Disney, impressive location, huge heated swimming pool with wrap-around sundeck and dynamic water features, fishing pond, sand volleyball, tennis and basketball courts. There is a special play area for our younger visitors and an area where you can even have your own family BBQ at our picnic area.

Superhost

Home in Spring Hill

4.79 out of 5 average rating, 24 reviews

Bear Spring

Enjoy a memorable visit when you stay in this unique place. Enjoy all Weeki Wachee has to offer. Take a short paddle down the canal to the crystal clear Weeki Wachee river. Bring your boat or rent one for your stay and see everything the Weeki River has to offer, or go exploring to the Gulf of Mexico. Go scalloping or float in the flats. This location is an example of the best of both worlds.