Holiday rentals in Leesburg

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Top-rated holiday rentals in Leesburg

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

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Guest favourite

Home

4.92 out of 5 average rating, 133 reviews

(Discounted Rates) Vacation Home (4 Miles Disney)

We have the perfect vacation home for You! Fully equipped 3 bedroom home with patio and pool overlooking a pond and conservation area. Just a 10 minute drive from Disney yet in a quiet gated community with playground. Sleeps 6 guests in 3 bedrooms. All beds are new, including king size bed in master bedroom. Folding cots and full size folding crib are available. Master bedroom has a private master bath. Close to local shopping ,dining and attractions. Request heated pool for additional fee.

Guest favourite

Cottage

4.9 out of 5 average rating, 232 reviews

Be Our Guest Sandcastle Cottage 81

Located-Encore Tropical Palms RV Resort 5 min to Disney property and minutes away from various restaurants. Old Town and Fun Spot are right next to the property. New renovated floors just installed! (May 2023) Has private bedroom with queen bed and upstairs loft with 2 twin beds for the kids. Newer sofa and recliner and washer/dryer. Stainless Steel Appliances and granite tile counter tops in kitchen. Smart TV in living room. Resort style pool with kiddie area. Miniature Golf area. Free WiFi

Guest favourite

Townhouse

4.97 out of 5 average rating, 110 reviews

Regal Oaks Resort Lake View 2BR near Disney Parks

Our gorgeous 2 bed 2.5 bath DELUXE townhome is located in the pristine Regal Oaks Resort located just behind Old Town theme park and minutes from Disney, shopping, restaurants & more. Inside our home you will find a living/dining room combo and a kitchen boasting stainless steel appliances and granite countertops. Upstairs an in suite beautiful Mickey decor guest room and one master suite with private balcony overlooking a beautiful pound view and huge conservation area (all rooms no carpet).

Superhost

Townhouse

4.66 out of 5 average rating, 165 reviews

@Look@ ~ Regal Oaks-4BD/3Bath/Hot Tub! ~ Sleeps 9!

* Comfortably accommodates 9 guests! * Private laundry and fully furnished kitchen! * Enjoy free Keurig coffee k-cups! * Screened porch with relaxing hot tub! * Just minutes drive to Disney World, Universal Studios, SeaWorld, and walking distance to Old Town! * Multiple activities and restaurants within walking distance! * Access to Regal Oaks Resort amenities - pool, waterslides, fitness center, clubhouse, mini market, business center, bar and grill, tennis court, and the list goes on!!

Superhost

Townhouse

4.85 out of 5 average rating, 104 reviews

4 BR - Sunny pool, forest serenity + near Disney !

-Spacious 4 bedroom / 3 bath townhouse in a beautiful quiet resort -Screened south-facing private pool, with the peace and quiet of the forest nearby -Barely 2 minute walk to clubhouse, with free use of 2 heated pools, hot tubs, cafe, bar and gym -Just 5 miles to DisneyWorld and even closer to many shops and restaurants & more -Flat screen TVs in living room and every bedroom -Newly updated well equipped kitchen -Washer & dryer -Free calls to Canada & US, WiFi, cable & high speed internet

Guest favourite

Townhouse

4.91 out of 5 average rating, 129 reviews

ENCANTADA, resort near DISNEY, upd 4 Rms 3 Baths

Modern 4 bedr 3 bathr lux townhouse, private heated pool(extra cost for heating) w/free resort facilities. Nicely furnished with all what you need. Close to great Clubhouse with lobby/reception, snack bar, all-year heated pools, training facilites and gameroom. Close to dining and shopping. Close to all parks, 10 min drive to Orlando attractions and 15 minute drive to famous Orlando shopping. Beautifully located with access to open space right outside pool and walkway around Secret Lake.

Guest favourite

Rental unit

4.87 out of 5 average rating, 214 reviews

Modern Great Villa near Disney & Parks

This place is 5 up to 20 minutes to all of orlando's amusement and water parks!. One of the best units in this resort, just book and see for yourself. An excellent unit with great reviews. There is an awsome pool and jacuzzi onsite (Please note, sometimes the jacuzzi breaks down and may not work during your stay). high speed wifi. easy smooth self checkin with a private keypad code that is being replaced between each new guest, walking distance to many shops and plazas, free parking.

Superhost

Townhouse

4.88 out of 5 average rating, 134 reviews

Lovely Townhome with Crib and Lovely King Room

Peaceful, bright, and inviting space - Gated Townhouse Community. Enjoy Convenient - less than 30 minutes to Orlando Theme Parks . Tall ceilings & great light. Brand-new Kitchen and Ac Unit ! Modern style, comfortable mattresses, outfitted kitchenette. Easy parking. TV with Cable. As much privacy as you want, responsive hosts. Addtionally, it includes amenities for babies , Playard , Toddlers with a high chair for eating with child utensils and plates.

Guest favourite

Cottage

4.98 out of 5 average rating, 107 reviews

1BD Cottage "Limoncello" in Margaritaville

Welcome to your own island-inspired oasis. Our charming cottage is the perfect home base for your next dream Orlando vacation. The unit comes with all the comforts from home but worlds away. Conveniently located minutes from the Disney parks, a state-of-the art water park and newly opened 196,000 square foot shopping and dining district with multiple dining food and beverage options & brand-new movie theater. All Pets Must Be Preapproved :)

Superhost

Apartment

4.85 out of 5 average rating, 112 reviews

Beautiful Windsor Palms Condo near Disney!

The Windsor Palm Condo is located in a very suitable area. This beautiful gated resort is just minutes away from Disney (4 mi), Walmart ( 2 mi ), gas stations (2 mi), shopping centers (2 mi) and restaurants (2 mi). The gated community is great for family and children. The resort has heated hot tubs, pools, and a kiddie splash park. Guests are also able to enjoy the poolside bar with food, gym, movie theater, Wifi, and a convenience shop!

Superhost

Rental unit

4.77 out of 5 average rating, 149 reviews

*Magic and Lovely* best Resort location in Orlando

Welcome to the magic and lovely apartment located at the best resort community of Vista Cay, in Orlando. You can enjoy the resort style with no extra fee. The apartment is located at the first floor, the best access to everything, centrally-located place. Close to the major parks, outlets, restaurants, entertainment, International Drive and much more. The best location to stay in Orlando.

Guest favourite

Rental unit

4.99 out of 5 average rating, 106 reviews

Relaxing 2BR Lakeview Retreat Close to Attractions

Relaxing getaway with gorgeous lake views in historic Windermere just minutes from Disney, Universal, and all Orlando-area attractions. Skip the tourist traps and retreat to this charming, newly renovated apartment in quiet, old Florida. Perfect for families visiting the parks or anyone seeking a quiet getaway.