
Holiday houses 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 $52 NZD 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 and kid-friendly amenities

Pet-friendly accommodation
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

Wi-Fi availability
190 of Leesburg holiday rentals include Wi-Fi 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.

Cozy Lady Lake Guest House
Private guesthouse in a quiet, rural area of Lady Lake. 1 bedroom, 1 bath, furnished with pool privileges. Kitchen, dining bar, living room and sunroom. Sunroom opens to the pool deck and sparkling blue pool, which is completely privacy-fenced in a common area shared with the owners. Suitable for 1 or 2 adults. Central heat and air, 40” Smart Television , WiFi, washer and dryer. Bed linens and bath towels provided. Kitchen with full sized refrigerator/freezer ice maker and electric stove.

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😀

Treasure Island Getaway Kayak and Mini Golf
Your ultimate destination for fun and relaxation! Kayak to serene Lake Griffin Fish from the dock or experience world-class bass fishing in the Harris Chain of Lakes. Play 6-Course Mini Golf for some friendly competition. Watch a movie on our outdoor big screen under the stars. Relax by the campfire while swinging in the breeze. And when you're ready for even more fun, we’ve got you covered with: Darts Arcade basketball Gaming System Shuffleboard Cornhole Ping Pong A plethora of board games!

Luxury loft in a magical location.
Enjoy a stylish experience at this luxurious accommodation located in the heart of Leesburg, just an hour from all of Orlando's theme parks and minutes from the charming town of Mount Dora. Upscale restaurants, bars, cafes, art galleries, and an amazing park are all within a 5-minute walk. Enjoy this magical getaway, perfect for couples. You'll feel like in a movie strolling through the streets with their vibrant atmosphere. We also offer a picnic service to make your experience unforgettable!

Waterfront cottage Haynes Creek
Enjoy all central Florida has to offer, at this cozy waterfront cottage, on Haynes Creek, part of the Harris Chain. Fish from the dock, or bring your own watercraft, you have your own boat slip. Explore the area on our paddleboat, kayaks or paddle board. If its shopping and nightlife you enjoy we are close to Leesburg, Eustis, Mt. Dora, Tavares and the Villages. Or maybe you would enjoy watching wildlife and exploring one of the many parks or trails in the area. Central Florida has it all.

The Lake House
Newly renovated home on Lake Eustis Canal. This lake is part of the famous Harris Chain of lakes. This home offers 2 large living spaces, a Full Kitchen, 2 Bedrooms and 1 Full bath. You will not have access to the owners closet or use of personal watercraft or boats, feel free to fish or bring your own water sports during your stay. Its very quiet area for relaxing or event participation, We are only 10 mins from Publix, ~15min to beautiful Downtown Mt Dora or ~1 hour to International Drive.

~Venetian Gardens Peaceful Home~
Located walking distance from Venetian Gardens Park which has boat ramp, volleyball court, marina and walking path. Quiet neighborhood suitable for walking, jogging and biking. Near to various holiday events including bass fishing tournament. House has 3bedrooms (4 beds - 2 Queen and 2 Twin) 2 full bath and can accommodate up to 6 people, with 3TV’s. Office room with 32” monitor, keyboard, mouse, HDMI and network cable. WiFi 6 up to 900Mbps. Disney World and beaches are an hour away 🏖️

Charming Lake Harris With Private Boat Parking
Enjoy sunny Florida with a huge screened in porch where you can relax on the wicker patio couch, grill, or sit by the firepit. With nearby access to Lake Harris (part of the Florida Harris Chain of Lakes), this is the perfect place to stay for the year round fishing tournaments. The boat ramp is a mile from the house and our driveway can easily accommodate 2 trucks with boats plus 2 more in the yard. Our quiet and safe location is 35 minutes from Orlando, and 1 hour from Daytona and Tampa.

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

New Luxury Home-Pool-Waterfront View-3 King Suites
Enjoy this unique, tranquil getaway in a new 2023 home less than 3 miles from Sawgrass Grove (nightly entertainment, restaurants), and only a few blocks from Mickylee Pitch and Putt, Jubilee Putting Course, and the new Franklin Recreation Center. Ezell, Homestead, and Citrus Grove Rec Centers are all under 3 miles away. Back yard with lanai, pool with fountain, pond, and trees is a RARE find in The Villages! 3 king bedroom suites! Golf cart (4 seats) available for an additional fee.

Entire private home/heatedpool/boat or rv parking
3 bedroom 2 bath spacious private home with heated pool. Conveniently located. Just a few minutes away from grocery stores, bars/restaurants, malls, movie theater, basically everything you need and more! 5 min to world famous fishing on Harris Chain of Lakes! 15min to downtown Mount Dora. 50min to Orlando and all its theme parks (Disney world, Seaworld, etc) Why pay top rates at cramped hotels when you can book your own spacious private home with us? Save, be comfortable and book today!

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.
Popular amenities for Leesburg holiday rentals
Other great holiday rentals in Leesburg

Cozy Lake Cottage w/ Hot Tub + Boat Parking

Lakefront Magic Wilderness Cabin

Fisherman's Cottage

Beautiful 2 Bedroom Home in The Villages!

Rustic Modern Retreat w/ Private Pool – Leesburg

Lakefront home chain of lakes & near Mount Dora

Leesburg Fl Gem. Near Lakes, Springs & Theme parks

Eden Escape Suite, Lake Harris, Florida
When is the best time to visit Leesburg?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sept | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $255 NZD | $262 NZD | $262 NZD | $227 NZD | $213 NZD | $194 NZD | $206 NZD | $201 NZD | $201 NZD | $212 NZD | $219 NZD | $220 NZD |
| 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
- Weeki Wachee Springs
- Universal Orlando Resort
- Disney Springs
- SeaWorld Orlando
- Orlando / Kissimmee KOA
- Magic Kingdom Park
- Camping World Stadium
- Universal's Volcano Bay
- Epcot
- Rainbow Springs State Park
- Kia Center
- Disney's Animal Kingdom Theme Park
- Reunion Resort Golf Courses - Palmer & Watson
- University of Central Florida
- Discovery Cove
- Old Town
- ESPN Wide World of Sports
- Tinker Field
- Disney's Hollywood Studios
- ICON Park
- Aquatica





