Leesburg, FL Vacation Rentals

Our Favorite Vacation Rentals in Leesburg

  • Fly-in place to stay close to The Villages
     Country House
    Booking.com
    From
    $150
  • Chic Tavares Home w/ Lake Dora Private Dock, Patio
     3br Home/Apartment
    HolidayLettings
    From
    $290
  • Reunion Raven, 8 Bedrooms, Encore Club, Private Pool and Spa, Sleeps 18
     Country House
    Booking.com
    From
    $854
  • Relaxing Country Cottage near The Villages, FL
     3br Home/Apartment
    HolidayLettings
    From
    $298
  • Sleeps 7--1913 Historic Home 40 mins to Disney
    Good2br Home/Apartment
    Airbnb
    From
    $121
  • Deckhouse
    Excellent3br Home/Apartment
    Airbnb
    From
    $310
  • Florida style ranch house, Leesburg
    ExcellentHome/Apartment
    Airbnb
    From
    $45
  • Relax in Style - the Village of Pine Hills
     3br Home/Apartment
    Airbnb
    From
    $155

Check prices for these upcoming dates

Leesburg Vacation Rentals with a Pool

  • Silver Lake Guest Pool House
    Excellent2br Home/Apartment
    Airbnb
    From
    $113
  • Lady Lake Guest House
    ExcellentHome/Apartment
    Airbnb
    From
    $71
  • Spacious Villa near Brownwood
    Excellent2br Home/Apartment
    Airbnb
    From
    $107
  • Comfortable room with attached bathroom
    ExcellentHome/Apartment
    Airbnb
    From
    $73

Leesburg Vacation Rentals with Wi-Fi

  • Alexeliz’s place! Come & enjoy it!
    ExcellentHome/Apartment
    Airbnb
    From
    $34
  • Waterfront Paradise on Harris Chain of Lakes
    Excellent2br Home/Apartment
    Airbnb
    From
    $205
  • 3-bedroom house with an amazing lake view
    Good3br Home/Apartment
    Airbnb
    From
    $140
  • "Quality Plus" Vacation Home
     3br Home/Apartment
    Airbnb
    From
    $102

Leesburg Pet-Friendly Vacation Rentals

  • Cypress Point Cottage
    ExcellentHome/Apartment
    Airbnb
    From
    $102
  • RV Retreat Studio HOP2GLAMPING@Joyce's loyal place
    ExcellentHome/Apartment
    Airbnb
    From
    $68
  • "The Field House" at Far Reach Ranch
    Good3br Home/Apartment
    Airbnb
    From
    $129
  • 3/2 Luxury Villa, Walking Distance To Lake Sumter
    Excellent3br Home/Apartment
    Airbnb
    From
    $191

Leesburg Travel Guide

Leesburg is a great place to go on holiday as it's located just northwest of Orlando. The city is an awesome spot for family fun, a couples’ getaway or a long weekend away with friends. Leesburg Florida is mainly known for being centrally located to all that Florida has to offer.

Things to Do in Leesburg

Whether you are looking for excitement, recreation, shopping or you just want to relax, there's something for all types of travelers in Leesburg. Walt Disney World Resort is just a short drive south and is a must-visit for anyone in Florida. Devote a full day to the rides, characters, and variety of attractions at the park -- it's sure to be a day none of your group will forget. Equally exciting is the Epcot Center and Harry Potter World at Universal Studios -- just remember to bring a fully charged camera!

Alternatively, for the outdoor enthusiasts, the Ventian Gardens Park and Lake Okahumpka Park are perfect spots to spend warm summer's days.

Best Places to Stay in Leesburg

The downtown area is best to stay in to be close to all the attractions, restaurants, and stores; it's also where the largest selection of vacation rentals are. Some of which are pet friendly, and most of which have fully equipped kitchens, large living areas, and multiple bedrooms and bathrooms.

Best Time to Visit Leesburg

The best time of year to visit Leesburg is during the spring months when the weather is warm but not too hot, perfect for exploring and having fun at the various theme parks.

Food in Leesburg

The two places that stand out are Turner's Kitchen and Bar which is known for having some of the best New American food in the area. If you prefer breakfast, then you’re going to want also to check out Breakfast Station, a local favorite in Leesburg.

Price and Availability in Leesburg

Most expensive
Most availability
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The cheapest day to stay at a vacation rental in Leesburg tends to be Tuesday, while the most expensive day tends to be Saturday. Vacation homes in Leesburg tend to be busiest on Saturdays, while it tends to be much quieter on Tuesdays.
The most expensive month to stay in a vacation rental in Leesburg is in April, while the cheapest month is in June. The most popular time to book a vacation rental in Leesburg is in the high season in March. Leesburg has its low season in August, when less people are visiting and the vacation home occupancy rate drops.

The Weather in Leesburg

Rainy days
87° 38°
2
85° 37°
5
80° 28°
4
87° 49°
0
85° 42°
2
88° 53°
4
93° 60°
8
96° 71°
6
94° 71°
7
94° 71°
5
95° 72°
2
92° 53°
2
Nov
Dec
Jan
Feb
Mar
Apr
May
Jun
Jul
Aug
Sep
Oct
Rainy days

This climate histogram shows you the weather patterns in Leesburg. The warmest months in Leesburg are July and April, when temperatures reach 96 ˚F. The coolest month is December, when temperatures drop to 28 ˚F. The wettest month in Leesburg is August with 8.28 inches of rain, while the driest month is November with 0.49 inches of rain.

What Expert Travelers Think

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  • — I love that AllTheRooms has everything in one place when I need to find accommodations that fit my family. Plus it provides all the details I need to help me make the best choice. I often recommend AllTheRooms to friends and family visiting NYC and they agree that it’s a great. Such a time saver!

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  • — I love AllTheRooms because it enables me to compare a range of providers in just one search. I'd normally spend time checking prices across a range of platforms by visiting different websites one-by-one, so this helps me to save time on my accommodation searches while planning my upcoming trips

    Kacie Morgan
    Kacie MorganThe Rare Welsh Bit

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