
Holiday rentals in Leesburg
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Quick stats about holiday rentals in Leesburg

Total holiday rentals
Explore 200 holiday rentals in Leesburg

Nightly prices starting at
Leesburg holiday rentals start at €26 per night before taxes and fees

Verified guest reviews
Over 5,060 verified reviews to help you choose

Family-friendly holiday rentals
140 properties offer extra space & child-friendly amenities

Pet-friendly holiday rentals
Find 80 rentals that welcome pets

Holiday rentals with a pool
60 properties feature pools

Rentals with dedicated workspaces
110 properties have a dedicated workspace

Wifi availability
190 of Leesburg holiday rentals include wifi access

Popular amenities for guests
Guests love Self check-in, Gym and BBQ grill across Leesburg rentals

4.9 Average rating
Leesburg stays are highly rated by guests – averaging 4.9 out of 5!
Top-rated holiday rentals in Leesburg
Guests agree: these stays are highly rated for location, cleanliness and more.

Eden Escape Suite, Lake Harris, Florida
Settling into this luxuriously curated boutique suite, you may come to agree with lore that the original Garden of Eden was nearby. Bask in the rejuvenating spring waters flowing through all taps and feeding the pool just a three minute stroll to Lake Harris, a premier bass fishing lake in a chain that leads to the Atlantic. From the comforts of your private efficiency immerse in the outdoor privacy of your patio garden soaking up serenity in your vintage claw-foot tub, ah the perfect choice.

Royal Oak Lakeview Serenity
Spend your nights under a 400-year-old live oak in a freshly renovated 57' era lakeview bungalow with an old Florida feel! This amazing property is a 3/2, 2100 sq ft home on a 1/2 acre featuring amazing Lake Views and boat dock access to Big Lake Harris , and covered RV carport with power hook up. Great location with 3 major restaurants in walking distance, Publix and at least a dozen other dining and entertainment options are minutes away. Attractions and The Villages just 20-30 minutes away.

3/2 Designer Home W/ Golf Cart
Make this home your Villager get away! This is a designer home fully furnished with everything you will need for your vacation. This home is perfectly located minutes away from Sawgrass where you can enjoy live music every night. 🎶 The home is only an 18 minute drive from Brownwood which is a crowd favorite town-center. Home comes with a 4 seater golf cart perfect for adventuring to the pickleball courts, golf courses, pools & so much more! Come enjoy the sunshine in the beautiful Villages😀

Luxury home with a pool and 3 bedroom
Spacious water front home that sits on a beautiful freshwater canal with access to the great Lake Griffin. Offers a perfect blend of luxury & comfort, a perfect space for entertaining & relaxation. Escape the pressures of everyday life, enjoy the outdoors in style with the lanai in the rear of the home, perfect for barbecuing or lounging while enjoying the water view. Has access to onsite community boat ramp, campgrounds, nature trails, kayaking, major roads, stores, restaurants, and more.

Latitude Adjustment
Change your latitude in this beautiful two bedroom, two bathroom Patio Villa in The Villages. Located in the Village of Newell, this spacious and modern home has everything you need to make your stay relaxing and fun, including a golf cart! Enjoy a cup of coffee from the Keureg after your morning stroll on one of the nearby nature trails. Pools, pickleball and golf are all five minutes by golf cart, along with dining and entertainment at Sawgrass Grove and twelve minutes to the new Eastport!

The Golden Anchor
Time to relax and soak in Florida's beauty on Lake Harris-Only 1 minute by boat to the Dead River which leads to Lake County's infamous Chain of Lakes. Fishermen welcome! Plenty of space for boat trailers with a public boat ramp 1 mile away. OR Dock your boat at our private marina and get an early hassle-free start to your day of fishing! Cook your fresh catch in our well equipped kitchen. Gather around the firepit for marshmallows, stories, & star gazing! Less than 2 m to restaurants, etc.

Silver Lake Guest Pool House Very Private !
The Silver Lake Pool Guest house Is your home away from home 1400 sq feet plenty of room! The pool house is a peaceful place to relax or take a swim in a large salt water pool. Mt Dora Tavares, Eustis 10 to 15 minutes away from Pool house Forty five minutes Daytona, Tampa Smyrna beach and parks Minutes from food stores restaurants malls Full kitchen also grilling. We are happy to help you with your needs ! Home is great for couples families, solo adventurers, and business travelers

Waterfront Cottage on The Harris Chain in Leesburg
Cozy waterfront cottage on Haynes Creek. Whether its relaxing, fishing from your own dock, boating the Harris chain, paddle boarding, birdwatching, use our kayaks or pedal boat, or exploring the nearby towns and springs... we have it all. Fully equip kitchen, outdoor grilling area, wifi and cable, parking, laundry, gas fire pit on your private deck, boat parking at your dock or book a tour with Monster Bass fishing. Walkable to nearby stores or Gator Bay for a drink, meal, or music!

Fisherman's Cottage
Two bedroom one bath. Canal front on Harris Chain of Lakes. Less than two(2)minutes to Lake Eustis. Fenced large back yard, pet friendly. Fully equipped kitchen . Laundry room with new washer and dryer. Fire pit in screened porch area. Gas grill with all grill appliances. Boat trailer parking and dock provided. Central A/C. High speed internet. Indoor and outdoor Streaming ready TVs. One hour to each coast and one hour to all major theme parks,close to Leesburg and Mt Dora. Enjoy

3-BR 2-BA house-amazing lake view and boat parking
Enjoy the tranquility of this lakefront getaway at Silver Lake in Leesburg, FL. This property is located in a secluded upscale residential neighborhood, yet still only few minutes away from SR 441, plenty of restaurants and the Lake Square Mall. Enjoy beautiful sunsets overseeing Silver Lake which is across the street from the house. Over 1 acre of land with lushful native trees and large lawn. Butterflies, birds, wildlife such as rabbits, and armadillos can be spotted.

Lakefront home chain of lakes & near Mount Dora
Relax with the whole family at this peaceful place to stay. Florida lifestyle at its best! Enjoy your morning waking up to a spectacular sunrise and panoramic views of gorgeous Lake Eustis. Bring your own boat or get a rental to go fishing to enjoy many of the lakeside accessible restaurants. Or visit the historic town of Mount Dora with its wonderful boutiques. Many restaurants and stores nearby. Just an hour from the theme parks, and Orlando International Airport.

The Lake Harris Bungalow
The newly finished Lake Harris Bungalow offers fun, sun & relaxation! Sitting directly on Lake Harris this in-law suite offers amazing views from its 2 beds (queen & twin XL), full bathroom, kitchen w/ full size appliances, WiFi/TV, covered parking (with power for boat/EV charging) and furnished screened in back porch overlooking the lake (with bbq grill). We promise a relaxing & peaceful stay. You're going to love it here!
Popular amenities for Leesburg holiday rentals
Other great holiday rentals in Leesburg

Casa Bella: 3 Bedroom 2 Bath House Sleeps 6

Treasure Island Getaway Kayak and Mini Golf

Lakeside Landing on Lake Dora w/ Boat Dock

Cozy Lake Cottage w/ Hot Tub + Boat Parking

Guest House Pool Boat Parking

Angler's Landing near Lake Harris/ Boat Parking

Paradise on Lake Harris Apt #202

Waterfront! The Dora Canal Escape!
When is the best time to visit Leesburg?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sept | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | €128 | €131 | €131 | €114 | €107 | €97 | €103 | €101 | €101 | €106 | €110 | €110 |
| Avg. temp | 16°C | 18°C | 20°C | 22°C | 25°C | 27°C | 28°C | 28°C | 27°C | 24°C | 20°C | 17°C |
Frequently Asked Questions
What are the best places to stay in Leesburg?
Travelers frequently choose to stay near the historic downtown for walkable access to parks, shops, and restaurants, or opt for accommodations close to the lakes for a quieter retreat. Both areas have a mix of homes, cottages, and condos available.
What are the best things to do in Leesburg with kids?
Children can enjoy playgrounds, interactive learning spaces at local museums, and family-friendly events in Leesburg. Outdoor activities like fishing, paddle boating, and exploring shaded boardwalk trails are also popular with families.
What are some of the best things to do in Leesburg?
Explore the natural beauty of area lakes, take a stroll through the historic downtown, or discover local arts and food scenes. Boating, golfing, and seasonal festivals are all frequently suggested activities.
How is the weather in Leesburg?
Leesburg has warm weather much of the year, with summer highs near 92°F (33°C) and frequent rainfall, particularly from June to August. Winters are mild, with daytime temperatures around 70°F (21°C), making outdoor activities comfortable.
When is the best time to visit Leesburg?
Late fall through early spring is often recommended in Leesburg for milder temperatures and lower humidity. Visitors also enjoy spring and fall festivals that highlight local music and food traditions.
What are the best places to visit in Leesburg?
Popular spots in Leesburg include the historic downtown district, scenic lakefront parks, and local museums. Many visitors also explore golf courses, community theaters, and nearby natural areas for outdoor recreation.
What are some hiking trails in Leesburg?
Leesburg has walking and hiking trails in local parks, nature preserves, and reserves, many with shaded pathways and boardwalks for observing wildlife. These trails are often flat and accessible for a range of fitness levels.
What are some family activities we can do in Leesburg?
Families can enjoy lakeside parks, picnic areas, and playgrounds in Leesburg, along with opportunities for fishing, boating, and nature walks. Local museums and community events also provide kid-friendly activities.
What are some of the best day trip ideas from Leesburg?
Around Leesburg, travelers often explore regional springs, wildlife preserves, or small historic towns with antique shops. Lake-based recreation and scenic gardens are also frequently suggested for a change of pace.
Are there any pet friendly accommodations available in Leesburg?
Leesburg has pet-friendly vacation rentals, and some hosts welcome pets with fenced yards or nearby walking trails. Public parks and several local eateries with outdoor seating accommodate guests traveling with animals.
What are some local tips for visiting Leesburg?
Locals often recommend visiting farmers markets for fresh produce and handcrafted goods, especially on weekends. It is also a good idea to check for seasonal events at parks and downtown spaces to experience the area’s traditions.
What is Leesburg known for?
Leesburg is recognized for its chain of lakes, boating opportunities, and vibrant historic downtown. The area is also known for hosting classic car events and having a strong sense of local community.
What are the best hidden gems to explore in Leesburg?
Explore the nature preserves around Leesburg for birdwatching, or stroll historic neighborhoods filled with unique architecture. Art galleries and locally owned shops are also frequently suggested for travelers seeking quieter spots.
What are the best foods to try in Leesburg?
Leesburg’s local cuisine often highlights Southern-inspired dishes, fresh fish, and barbecue, alongside citrus-based desserts reflecting the area’s agricultural roots. Diverse restaurants provide comfort food, international flavors, and seasonal produce.
What should I bring for a trip to Leesburg?
Pack lightweight clothing, sun protection, and comfortable shoes for exploring parks and outdoor areas. Bringing a light jacket is helpful in the cooler months, and rain gear can be useful during summer’s frequent afternoon showers.
What is the nightlife in Leesburg like?
Leesburg has laid-back nightlife with local bars, breweries, and live music venues. Enjoy evenings with live bands, open mic nights, and pub-style dining around the historic downtown area.
What are the most popular events or festivals in Leesburg?
Leesburg is known for seasonal festivals centered around music, local food, and classic cars, often drawing visitors in spring and fall. Community fairs and holiday parades are also frequently suggested for those interested in local traditions.
Are there family friendly vacation rentals in Leesburg?
Leesburg has a variety of family-friendly vacation rentals, including spacious homes with outdoor play areas and condos near parks. Many hosts provide features like kitchens and extra bedrooms to help travelers feel at home.
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- Walt Disney World Resort
- Universal Studios Florida
- Orange County Convention Center
- Universal Orlando Resort
- Weeki Wachee Springs
- Disney Springs
- SeaWorld Orlando
- Orlando / Kissimmee KOA
- Magic Kingdom Park
- Camping World Stadium
- Epcot
- Universal's Volcano Bay
- Kia Center
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- Disney's Animal Kingdom Theme Park
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- University of Central Florida
- Old Town
- ESPN Wide World of Sports
- Disney's Hollywood Studios
- Tinker Field
- Aquatica
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