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.

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Guest favorite

Home in Astor

5 out of 5 average rating, 12 reviews

Blackwater Bunkhouse

Newly Renovated multiple living spaces with own entrance great for large groups of multiple families. St John’s waterfront and close to several springs and restaurants by boat or car. Plenty of parking and also has full 30 rv spot available. 2 screen porches overlooking water. Fire pit with plenty of seating. Gas grill, Smart TV’s in all rooms. Quality mattress. Full kitchen upstairs with 2 bedrooms 2 full baths. Downstairs has 2 bedrooms 1 full bath. Efficiency kitchen and laundry. 2 pull outs.

Superhost

Vacation home in Orlando

4.87 out of 5 average rating, 47 reviews

Grand 3BR/3.5BA Resort between Disney & Universal.

The absolute best location in Orlando. Beautiful resort townhome located: 10 min to Universal. 15 min to Disney. 10 min to SeaWorld. 15 min to Orlando airport. WALKING distance to Convention Center, Top Golf, and Indoor Cart Racing. Hungry: 5 min to Restaurant Row and 5 min to Publix for groceries to prepare home-cooked meals in a full kitchen. Home: King; Queen, 2 Twins and Sofa-bed. Free Wifi. Cable. 3 ensuites. Free parking. Resort: large heated pool, gym, basketball, 2 mi lake trail.

Guest favorite

Home in The Villages

4.94 out of 5 average rating, 86 reviews

1199 Merryweather - Walk to Lake Sumter Landing Sq

Wow! Gorgeous 2br/2ba courtyard villa; 5-star reviews. Walk to Creekside Landing pool & town square in THE most sought after location in the entire community. Private yard. Granite counters, vaulted ceilings, big birdcage, French doors & vinyl plank floor. Zero carpet. Newer recliners & patio chairs & new sofa in 2024. King in master. Queen in guest br. Cable. WIFI. Rent a golf cart if you like. No pets here any longer. I manage a pet friendly 3br across street (sleeps 6). May-Dec 2025=5nt min.

Guest favorite

Home in Kissimmee

5 out of 5 average rating, 16 reviews

Disney Vacations Oasis

Experience the best of Disney's area with the comfort and luxury of our home. Whether you're here for adventure or relaxation, we provide everything you need for an unforgettable stay. We prioritize your health and safety. Our home undergoes a thorough professional cleaning and sanitization process prior to your arrival, ensuring every surface is spotless and ready for you to enjoy. Great amenities, including lazy river, restaurant, bar, gym and everything you may need during your stay.

Guest favorite

Apartment in Mount Dora

4.96 out of 5 average rating, 27 reviews

Lovely Historic Cottages Mount Dora, Rendezvous.

1 Bedroom (sleeps 3) This second-floor (500 square feet) studio style unit overlooks the courtyard. Beautiful French toile décor, queen size bed with built-in drawers, gorgeous heart of pine floors, chaise lounge, private reading area with chair and ottoman, romantic clawfoot tub with full European Style hardware and shower all add to the charm and elegance of this cozy unit. The Rendezvous has a TV, fully equipped kitchenette, central heat & air and tons of charm. Directly downtown.

Superhost

Townhouse in Davenport

4.83 out of 5 average rating, 36 reviews

Vacation Townhome Davenport ChampionsGate

This rental is gorgeous Townhome located in Davenport Champion Gate, and it sits in the perfect spot for family vacation, meeting friends, or a couple’s getaway. You will be close to everything when you stay at this centrally-located place. You have plenty of choices from Disney parks, Water parks, Universal Studios, Canoeing, Obstacles Park, Paddleboard to Shopping, and Nights on the Oldtown. There’s something for everyone in your group. Recreation area with FREE mini golf, and pool

Guest favorite

Townhouse in Kissimmee

5 out of 5 average rating, 42 reviews

Unbeatable Experience Themed House w/Pool n Resort

Experience the ultimate vacation in our exquisite 4-bedroom, 3-bathroom haven, just a stone's throw away from the enchantment of Disney World and the thrills of SeaWorld. Nestled in the prestigious Story Lake Resort, this home sleeps 12 with the option of a plush queen-size air mattress. Every moment here is a memory in the making, with themed bedrooms that transport you to new realms. This is more than a vacation home; it's a key to unlocking a world of wonder and relaxation!

Guest favorite

Home in The Villages

4.92 out of 5 average rating, 13 reviews

The Sandpiper Villa

Located in the Village of Monarch Grove, this beautiful patio villa has everything you need to get away and have a relaxing vacation. Located minutes from shopping centers, golf courses, recreational centers with resort style pools, and so much more! Close by are Sawgrass Grove and Brownwood square, which host live music and entertainment every night! With a spacious layout, that is meticulously cleaned and well kept, and ample amenities, this villa has so much to offer!

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

4.93 out of 5 average rating, 183 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.

Superhost

Apartment in Davenport

5 out of 5 average rating, 3 reviews

Bahama Bay Resort * Disney Area

Bahama Bay is a Gated Resort just 10 miles from Disney! With 4 Pools * 6 Hot Tubs * A Splash Pad * Shuffleboard * Sandy Beach Area * Tiki Bar Restaurant * Walking Trails & More is a great place for a Vacation! * NO Resort FEE * Parking is FREE! Resort Villa * 2nd floor Villa * 4 Swimming Pools * 6 Hot tubs * White sandy Beach * On-site Restaurant Tiki & Bar * Beach Volleyball * Tennis * Pickle Ball * Basketball * Fishing * Nature Trails *

Guest favorite

Home in Crescent City

5 out of 5 average rating, 11 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