Leesburg, FL Vacation Rentals

Our Favorite Vacation Rentals in Leesburg

  • Reunion Raven, 8 Bedrooms, Encore Club, Private Pool and Spa, Sleeps 18
     Country House
    Booking.com
    From
    $391
  • 1474 Alesio - Guesthouse
    ExcellentHome/Apartment
    HolidayLettings
    From
    $57
  • Fox Haven Cottage
    ExcellentCottage
    HolidayLettings
    From
    $110
  • Chic Tavares Home w/ Lake Dora Private Dock, Patio
     3br Home/Apartment
    HolidayLettings
    From
    $290
  • Courtyard Villa in The Villages, Florida
    Good2br Home/Apartment
    HolidayLettings
    From
    $137
  • Relaxing Country Cottage near The Villages, FL
     3br Home/Apartment
    HolidayLettings
    From
    $298
  • 2 Bed 1 Bath Large Historic Home w/Extra Parking
    Good2br Home/Apartment
    Airbnb
    From
    $129
  • Florida style ranch house, Leesburg
    ExcellentHome/Apartment
    Airbnb
    From
    $45

Check prices for these upcoming dates

Leesburg Vacation Rentals with a Pool

  • Silver Lake Guest Pool House
    Excellent2br Home/Apartment
    Airbnb
    From
    $113
  • Spacious Villa near Brownwood
    Excellent2br Home/Apartment
    Airbnb
    From
    $107
  • Comfortable room with attached bathroom
    ExcellentHome/Apartment
    Airbnb
    From
    $57
  • Kelly's Dream Come True
    ExcellentHome/Apartment
    Airbnb
    From
    $85

Leesburg Vacation Rentals with Wi-Fi

  • Peace and Quiet
    Excellent3br Home/Apartment
    Airbnb
    From
    $113
  • Cozy Corner ~ Close to the Villages and Disney!
     3br Home/Apartment
    Airbnb
    From
    $155
  • 3-bedroom house with an amazing lake view
     3br Home/Apartment
    Airbnb
    From
    $129
  • A Taste of Florida-The Villages!
    ExcellentCountry House
    Airbnb
    From
    $85

Leesburg Pet-Friendly Vacation Rentals

  • Home in The Villages
    Excellent2br Home/Apartment
    Airbnb
    From
    $124
  • RV Retreat Studio NO CLEANING FEE ~HOP 2 GLAMPING
    ExcellentHome/Apartment
    Airbnb
    From
    $62
  • Spillway Cottage
    ExcellentHome/Apartment
    Airbnb
    From
    $110
  • CENTRAL FLORIDA LUXURY ESTATE
    Excellent5br Estate
    Airbnb
    From
    $593

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
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Powered by:
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
95 º72
2
92 º53
2
87 º38
2
85 º37
5
80 º28
4
87 º49
0
85 º42
2
88 º53
4
93 º60
8
96 º71
6
94 º71
7
94 º71
5
Sep
Oct
Nov
Dec
Jan
Feb
Mar
Apr
May
Jun
Jul
Aug
Rainy days

This climate histogram shows you the weather patterns in Leesburg. The hottest month in Leesburg is July, when temperatures peak at 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

  • — Site is easy to use; clean, laid out well, good colors and branding, fun logo and title that connects to the purpose of the brand. The blog, vacation destinations, and rental destinations is a great feature and really make the brand stand apart from other sites!

    Laurelle McVicker
    Laurelle McVickerLaurelle McVicker
  • — I love AllTheRooms because it is not only local homes for renting, and not only hotels, but everything combined. When I am about to book a place to stay, I usually spend a couple of hours looking through both hotel sites and local home sites, comparing the prices and places.

    Alli Sims
    Alli SimsAlli Sims
  • — I love All the Rooms because instead of having to check one place for home rentals, another for hotel, another for bed and breakfasts, and yet another for a room rental in a private residence, I can finally see EVERYTHING at one site; saving me considerable time

    Jeff Campbell
    Jeff CampbellMiddle Class Dad

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