Holiday rentals in Leesburg

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Top-rated holiday rentals in Leesburg

Guests agree: these stays are highly rated for location, cleanliness and more.

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Top guest favourite
The exterior of the villa is showcased, featuring a well-maintained facade with a garage and a driveway. Lush palm trees and neatly trimmed bushes contribute to the inviting landscape, while a white privacy wall offers additional seclusion. The dynamic sky adds a vibrant backdrop.
Villa in The Villages
4.99 out of 5 average rating, 71 reviews

Perfect location Lake Sumpter Villa w/ Golf Cart

Newly opened availability! January and February open for monthly stays. Please message me to inquire . Jan.1 - Jan.31 Feb.1 - Feb.28 5% discount if you book both months. Location, Location, beautiful 2 bedroom villa with 2-seater golf cart, is located in the desirable neighborhood of Creekside Landing. This villa is within walking distance of Lake Sumter Landing town square where you will find shopping, restaurants, a movie theater and FREE nightly live entertainment. Edgewater neighborhood Recreation Center with a pool, as well as Canal Street Recreation Center with activities such as shuffleboard courts, bocce courts, card rooms and so much more. This villa is beautifully decorated in a warm and inviting style. The kitchen is fully equipped with everything you’ll need to prepare meals and entertain friends. The living room offers plenty of comfortable seating with a flat screen TV. The master bedroom has a king size bed, flat screen TV, large walk-in closet and a private master bath with a walk-in shower, complete with towels and linens. The guest bedroom and guest bath comes completed with lines and towels for your guest’s comfort. There is a screened lanai with comfortable seating and a privacy wall . This villa comes complete with WiFi. With the purchase of resident ID cards you can use any of the 29 executive golf courses with no greens fees. You pay resident rates in greens fees at the 11 championship courses. You are also entitled to use any of the family- friendly and adult (30 and older) swimming pools, and organized activity swimming pools, There are over 1,000 organized activities each week through the recreation centers. Rates are based on double occupancy. Rates shown do not include taxes and additional fees

Top guest favourite
A sun-drenched pool area features a sparkling blue pool surrounded by comfortable seating. A table with an umbrella and colorful chairs offer space for relaxation. The sunroom with large windows provides views of the inviting outdoor space, enhancing the overall tranquil setting.
Home in Lady Lake
4.96 out of 5 average rating, 339 reviews

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.

Top guest favourite
The inviting exterior features a two-story home framed by lush green grass and mature trees. Arched windows and a symmetrical design enhance the charm, while a driveway leads to the front entrance, providing easy access to the peaceful surroundings.
Guest house in Silver Lake
4.98 out of 5 average rating, 425 reviews

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

Guest favourite
The backyard features a well-maintained mini golf course alongside a wooden deck with seating. Lush green grass and decorative stones surround the area, with a playground structure visible in the background. Palm trees and natural foliage provide a serene atmosphere.
Home in Leesburg
4.95 out of 5 average rating, 38 reviews

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!

Guest favourite
Home in Fruitland Park
4.93 out of 5 average rating, 46 reviews

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.

Top guest favourite
The exterior of a single-story home is showcased, featuring a well-maintained front yard with greens and flowering shrubs. A paved driveway leads to a two-car garage, while the entrance is framed by neat landscaping. The sky above is clear and bright.
Home in The Villages
4.95 out of 5 average rating, 21 reviews

The Villages, Citrus Grove home away from home

Create great memories at this centrally-located home, with an open floor plan with vaulted ceilings. The kitchen is well equipped and the living room has a queen size sleeper sofa and a smart TV (internet/WIFI). The master bedroom has a king size bed, walk in closet, smart TV, master bathroom and a work area with a desk and printer. The guest bedroom has a queen size bed, large closet and smart TV. Both bedrooms have black out curtains and hair dryers, and linens. Grill/2 bikes incl.

Guest favourite
A spacious saltwater pool is enclosed by a screened area, surrounded by lush greenery and landscaping. Lounge chairs and a small jacuzzi can be seen along the poolside, with sunlight reflecting off the water's surface.
Home in Leesburg
4.93 out of 5 average rating, 58 reviews

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!

Guest favourite
A wooden dock extends into the calm waters, surrounded by lush greenery and mature trees. Steps lead up from the dock to a cottage nestled among the foliage, offering a serene and natural setting.
Cottage in Leesburg
4.91 out of 5 average rating, 116 reviews

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!

Top guest favourite
A shaded gazebo with wooden seating is positioned on a concrete slab, surrounded by lush green grass. The cabin features a brown exterior and a welcoming porch, framed by trees and Spanish moss, offering a serene and natural setting.
Cabin in Leesburg
4.85 out of 5 average rating, 26 reviews

Lakefront Magic Wilderness Cabin

Make some forever memories at this unique and family-friendly place! Nestled on an acre of oak and cypress forest, The Magic Wilderness Cabin evokes the timeless beauty of early Florida lake life with a whimsical nod to it's original beginnings at a world famous theme park. The Magic Wilderness Cabin welcomes you to delight in the quiet nature of beautiful Lake Harris and the Harris chain while watching the sunset over the the scenic shores of the lake from our private dock

Top guest favourite
A comfortable seating area is provided with a pair of reclining chairs, featuring built-in cup holders. Nearby, a small dining space is set up with a textured table and two high-backed stools, creating a functional space for meals or games.
Camper van/Motorhome in Fruitland Park
4.98 out of 5 average rating, 62 reviews

Delightful 2- Bedroom Camper/RV with Boat Parking

RV with Queen size bed and seperate room with bunk beds. Bunk beds are a Full on the bottom and twin on top. A/C, Heat, Full Hookup, use of 3 smart TVs and Wifi included. Centrally located to Lake Harris, Lake Dora, Lake Griffin and The Villages, FL. Only 1 hour to Orlando. Quiet Area among the trees on 5 acres with ample room to park your boat securely next to the RV to charge over night. Owners onsite. Completely fenced and gated. 2 very friendly dogs also on property.

Guest favourite
Two cranes walk gracefully in shallow water at dusk, their reflections visible on the surface. A vibrant sunset fills the sky with shades of orange and purple, while soft clouds add texture to the scene. Lush greenery borders the water in the background.
Home in Silver Lake
4.89 out of 5 average rating, 169 reviews

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.

Top guest favourite
A peaceful dock area features two lounge chairs with plush white cushions, complemented by orange throw pillows. A small table holds a bottle of champagne and two glasses, set against a backdrop of calm lake water and a clear blue sky. Nearby, a cozy sectional offers additional seating.
Home in Leesburg
4.93 out of 5 average rating, 91 reviews

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.

Popular amenities for Leesburg holiday rentals

When is the best time to visit Leesburg?

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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 € 26 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 & 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

    200 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!

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