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Vacation rentals in Leesburg

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Top-rated vacation rentals in Leesburg

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

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Top guest favorite
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, 342 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 favorite
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.
Guesthouse in Leesburg
4.98 out of 5 average rating, 430 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 favorite
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
4.93 out of 5 average rating, 42 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!

Top guest favorite
A charming cottage is nestled among lush greenery and palm trees. A concrete pathway leads to the entrance, flanked by vibrant plants in pots. Stairs ascend to the front door, inviting guests to explore the cozy interior.
Home in Leesburg
4.98 out of 5 average rating, 99 reviews

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.

Guest favorite
Home in Leesburg
4.94 out of 5 average rating, 47 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.

Guest favorite
A modern single-story home is presented with a well-maintained front lawn and a driveway accommodating a dark-colored pickup truck. The exterior features light-colored siding and a garage door, complemented by a clear blue sky overhead.
Guesthouse in Leesburg
4.88 out of 5 average rating, 101 reviews

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.

Top guest favorite
An extended lanai features a dining table surrounded by cushioned chairs, with views of a heated saltwater pool and lush greenery beyond. Comfortable seating arrangements are designed for relaxation, while ceiling fans provide a gentle breeze throughout the open space.
Home in The Villages
4.98 out of 5 average rating, 102 reviews

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.

Top guest favorite
An inviting outdoor space features a spacious in-ground pool with a sunken hot tub nearby. The pool area is enclosed by a screened lanai, allowing for privacy. Light reflections dance on the water's surface, creating a peaceful ambiance.
Place to stay in The Villages
5 out of 5 average rating, 120 reviews

Safari themed private addition with pool/hot tub.

This special Guest house addition is close to everything in The Villages! Making it easy to plan your visit.! We are in The Village of Osceola Hills at Soaring Eagle Preserve. A short golf cart or car ride to Brownwood Square and Sumter Landing Square for dining, shopping, and dancing! A 5 min jaunt to two plazas for groceries, gas, and eating:-) Access to play over 50 golf courses at a minimal fee. Ask us about our easy 4 seater Golf-cart rental and upon request free Guest passes!

Top guest favorite
A cozy living space features a large television mounted on the wall and a wooden dresser. In the foreground, two bar stools are positioned by a counter. The kitchen area is visible in the background, showcasing wooden cabinetry and a tile backsplash.
Guesthouse in Tavares
4.99 out of 5 average rating, 146 reviews

The Landing Pad+Short Stroll to Heart of Tavares!

We are located in heart of Taveras where everything is walking distance-restaurants, pubs, the seaport, Wooton Park & the history museum! Sit on the patio while using the electric grill. Bring your boat! Plenty of off street park with easy access using the alleyway. Bathroom has a rain shower with 2 speeds. Full kitchen including all the basic amenities+kureig with refillable cups. Come & relax at this fun little spot & enjoy all we have to offer thanks for landing here!

Top guest favorite
A treehouse is illuminated by warm string lights, nestled among large branches under a deep blue sky. The structure features large windows allowing views of the surrounding greenery, with a cozy seating area visible inside. A wooden walkway leads to the entrance.
Treehouse in St. Cloud
4.97 out of 5 average rating, 1,118 reviews

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.

Guest favorite
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 Leesburg
4.89 out of 5 average rating, 173 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 favorite
Home in Leesburg
4.91 out of 5 average rating, 173 reviews

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.

Popular amenities for Leesburg vacation rentals

When is the best time to visit Leesburg?

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Avg. price€ 129€ 128€ 128€ 111€ 104€ 95€ 101€ 98€ 98€ 103€ 107€ 108
Avg. temp16°C18°C20°C22°C25°C27°C28°C28°C27°C24°C20°C17°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 vacation rentals in Leesburg

  • Total vacation rentals

    Explore 200 vacation rentals in Leesburg

  • Nightly prices starting at

    Leesburg vacation rentals start at € 26 per night before taxes and fees

  • Verified guest reviews

    Over 5,060 verified reviews to help you choose

  • Family-friendly vacation rentals

    140 properties offer extra space & kid-friendly amenities

  • Pet-friendly vacation rentals

    Find 80 rentals that welcome pets

  • Vacation rentals with a pool

    60 properties feature pools

  • Rentals with dedicated workspaces

    110 properties have a dedicated workspace

  • Wi-Fi availability

    190 of Leesburg vacation 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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  5. Leesburg