Holiday houses in Leesburg
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Top-rated holiday rentals in Leesburg
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The Boat House on Lake Dora - Downtown Waterfront
WATERFRONT! The Boat House is an 800sf private residence built directly over Lake Dora offering panoramic lakefront views. Located on Mount Dora's Famous Boat House Row, right in the heart of downtown Mount Dora, where you can roll out of bed and walk a few steps to one of the quaint coffee shops. The Boat House was once a tin boat shed with floors open to the water and housed two boats. Today, you will find warm, cozy furnishings, comfortable beds, a quiet location and sunsets every evening!
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.
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 grocery 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
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!
Beautiful house in Leesburg FL
Beautiful home in Leesburg, FL, offering all the amenities and services needed for a wonderful stay. Located near Venetian Gardens Park, Emeralda Marsh Conservation Area, Flat Island Preserve, The Villages, and just minutes from popular stores like Wal-Mart, Target, Publix, Dollar General/Tree, Ross, TJ Maxx, HomeGoods, Belk, Marshall’s, and more. Please note, for security purposes, a doorbell camera is installed facing the entrance. It only monitors the exterior for your safety and privacy.
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 also offer discounted pontoon boat rental prices for guests. We promise a relaxing & peaceful stay. You're going to love it here!
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!
TreeHouse in the Cloud, (Close toTheme Parks
The treehouse is a private getaway for a couple that want to experience the magic. Check out video tours on U-Tube. Type in Treehouse in the Cloud. There have been several movie and other photo shoots done on property. Please text request and details, and we can negotiate fees. Our other AirBnB is just next door; Country gem horses close to Theme parks [link] Which is 1,000 sq ft and sleeps six.
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.
The Faith Estate - A Lakefront Storybook House
Welcome to The Faith Estate, a historic 5-bedroom, 3.5-bathroom lake house in Leesburg, FL, near The Villages, Eustis, and Mount Dora. Perfect for reunions, retreats, or a relaxing getaway. Ideal for boaters, with space for multiple boats and trailers—great for Harris Chain of Lakes events. The estate also allows approved events. Submit details via Airbnb for approval before check-in. Unapproved events are not permitted. Event setups must respect property guidelines.
Dirty Dog Cottage
Come stay in our cute Florida cottage located at Dirty Dog Organic Farm. Relax at the Pergola and watch the Koi fish. We have chickens, Roosters, Goats and 2 sweet pigs. I am happy to help you feed the animals a treat. Leesburg Florida has many hiking trails, and water sports. The farm seems worlds away yet is only 10 minutes from downtown Leesburg and many other activities. The villages is also only a short drive away. The cottage is fully fenced in.
Popular amenities for Leesburg holiday rentals
Other great holiday rentals in Leesburg
Eagles nest
Amazing home in The Villages, FL
Bay Breeze Villa
3/2 Courtyard in The Village of Newell : Golf Cart
Cottage 34: Coconut Cottage | Dora Canal Court
Guest House Pool Boat Parking
Opal Oasis in The Villages
Entire 3 Bed Home, Pool, boat parking, by the lake
When is the best time to visit Leesburg?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $258 NZD | $256 NZD | $256 NZD | $222 NZD | $209 NZD | $190 NZD | $202 NZD | $197 NZD | $197 NZD | $207 NZD | $214 NZD | $215 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.
Quick stats about holiday rentals in Leesburg
Total holiday rentals
Explore 210 holiday rentals in Leesburg
Nightly prices starting at
Leesburg holiday rentals start at $51 NZD per night before taxes and fees
Verified guest reviews
Over 4,870 verified reviews to help you choose
Family-friendly holiday rentals
150 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
200 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!
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