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Places to stay near Leesburg

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Top-rated vacation rentals near Leesburg

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

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Top guest favorite

The exterior of the villa showcases a well-maintained façade with siding in soft gray tones. A golf cart is parked on the driveway, alongside a neatly landscaped area featuring rose bushes. The front entry is framed by two accent lights and features an inviting porch.

Home in The Villages

5 out of 5 average rating, 35 reviews

SpringHouse - 3 Bdrm Patio Villa in The Villages

Rare 3 Bedroom 2 Bath Villa in The Villages. Quick access to Florida’s Turnpike. A two minute walk to Dabney Adult Pool and Rec Center and a short ride to Franklin Golf and Sawgrass Town Square. Beautifully Furnished. Home features luxury vinyl flooring and carpet in the bedrooms. A patio with seating for 4 with grill outside and upgraded landscaping providing a nice relaxing location after your busy and active day in The Villages. The neighbors are wonderful, friendly and extremely welcoming.

The exterior of the villa presents a modern, single-story design with a welcoming front porch. A 4-passenger golf cart is parked on the driveway, surrounded by well-maintained landscaping and a neat lawn. Cloudy blue skies create a bright, inviting atmosphere.

Home in The Villages

5 out of 5 average rating, 12 reviews

Best of The Villages! 2BR/2BA Home with Cart & Am

Discover a delightful villa in The Villages, Florida, perfect for families seeking comfort and convenience. This charming single-level home features air conditioning, a fully-equipped kitchen, and a relaxing patio. Enjoy easy access to community pools, golf, and recreation in the desirable Village of Dabney. Explore nearby Sawgrass Grove for dining and entertainment, all while enjoying the included golf cart! Visit the new Dabney Recreation Center, copy and paste into your browser https://yout

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, 392 reviews

Silver Lake Guest Pool House

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

Top guest favorite

An outdoor patio area features a screened enclosure with a private swimming pool. Comfortable seating is arranged around the pool, and lush greenery surrounds the space, providing a serene environment. Potted plants add a touch of color, enhancing the tranquil setting.

Guesthouse in Deer Island

4.95 out of 5 average rating, 120 reviews

Sapphire Cottage - sleeps 6, on 5 acres with canal

On 5 beautiful wooded acres with a boat dock on the canal. Relax by the shared pool, enjoy a BBQ by the firepit, fish from the boat dock, enjoy nature, or simply read a book in the gazebo. Sapphire Cottage has a Master with a queen size bed, a fully equipped kitchen, 2 full size sofa-beds, dinning area for 6, and a full size bathroom. Whether you are looking to relax, enjoy the farm animals, or a bit of adventure we have the perfect location. We live in the main house across the cottage.

A charming green cottage is set among tall pine trees, featuring a wooden porch and a welcoming entrance. A small window is visible on one side, complemented by outdoor lighting. Bright flowers line the base of the cottage, enhancing its rural setting.

Tiny home in Groveland

4.95 out of 5 average rating, 104 reviews

Lovely Meadow Farm Cottage

This lovely farm cottage can be found in a secluded meadowland under various oaks and pines along a natural cypress dome. Spectacular star lit night skies accompanied by hooting owls, whippoorwills, and fire flies make for an unforgettable camp fire atmosphere. Amenities include an outdoor shower, washer, dryer, barbecue, fire pit, fishing and outdoor wrap around patio. Ponds, canals, and Florida wetland host a variety of birds, mammals, fish and reptiles including the Florida gator.

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

4.99 out of 5 average rating, 74 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 open living space features a full kitchen area with a dining table, along with a cozy seating area highlighted by a blue couch. Light floods in through large windows, showcasing a view of the screened back porch and the surrounding landscape.

Bungalow in Okahumpka

5 out of 5 average rating, 10 reviews

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!

Aerial view of The Faith Estate, showcasing the historic Victorian-style house surrounded by lush greenery and expansive lawns. The blue exterior contrasts with the vibrant landscape, while serene lake waters reflect the soft colors of the sunset sky, enhancing the natural beauty of the setting.

Home in Leesburg

4.9 out of 5 average rating, 125 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.

Top guest favorite

A cozy front entrance is shown, featuring a light exterior with a pink door. A decorative bench is positioned under a window adorned with potted plants. Green grass and a landscaped area with small shrubs frame the entry, complemented by a wooden fence in the background.

Home in Mount Dora

4.99 out of 5 average rating, 177 reviews

Golf Cart Add-on Option! Bright + Airy in Mt Dora!

Kick back and relax in this calm, stylish space. The Linen + Lavender on Seventh is bright, airy and so comfortable! This updated two bed, two bath will feel like home to you. Walk to downtown Mount Dora to explore the plethora of shopping, restaurants and sights for the day and come home and relax on the cozy back patio. There is plenty of parking in the spacious drive way, with room for four vehicles. You won't want to leave once you settle into L+L on Seventh!

The A-frame cabin features a striking black exterior with large windows that reflect the surrounding greenery. A spacious wooden deck is highlighted, equipped with a picnic table. Lush trees frame the cabin, creating a serene and inviting outdoor setting.

4.96 out of 5 average rating, 187 reviews

Cozy A-Frame Retreat w/ hot tub!

Escape to our cozy A-frame cabin, nestled amidst the serene beauty of nature. Just 10 mins from Santos Trailhead and 35 from Rainbow Springs! After a day of exploration, unwind in the private hot tub, gather around the bonfire pit for s'mores, or snuggle by the fireplace and stream your favorite movie. Whether you seek a romantic retreat or an extended family getaway, our A-frame cabin promises the perfect blend of nature's tranquility and modern comfort!

Top guest favorite

A swing adorned with vibrant flowers hangs from a large tree beside a modern, light-colored house. Sunny skies illuminate the patio area, where potted plants are arranged neatly. The lawn is well-maintained, featuring a mix of grass and decorative stone pathways.

Cottage in Clermont

4.9 out of 5 average rating, 113 reviews

Beautiful country house

Take the whole family to this fantastic place with many areas for fun. we have 5 acres of land just for you, beautiful country house in the only hills of the state of Florida, you will enjoy the tranquility, privacy, connection with nature and witness a beautiful sunset unparalleled, stay and observe the stars, spaces suitable for unique souvenir photos. Ideal area for cycling and walking. NOTE: if you want an event check our rates first

Top guest favorite

The exterior of a single-story home is displayed, featuring a light grey facade and a two-car garage. The driveway is clear of obstructions, and neatly manicured shrubs are positioned on either side of the entrance. A soft evening light casts a warm glow over the scene.

Home in The Villages

5 out of 5 average rating, 10 reviews

Chic 3/2 Home in The Village of Citrus Grove

Welcome to your perfect getaway in The Villages, Florida! This beautifully designed 3-bedroom, 2-bathroom home offers a blend of modern elegance and cozy charm, creating the ideal space for relaxation and entertainment. Just 1 mile from Sawgrass Grove Market and 7 miles from Brownwood Square, you’ll be close to live entertainment, dining, pools, pickleball, and golf—endless fun awaits!

Popular amenities for vacation rentals near Leesburg

Free parking on premises

Air conditioning

Condo rentals with wifi

A spacious living area features a comfortable sofa and two turquoise chairs, inviting relaxation. A large rug with geometric patterns anchors the space, while a modern art piece adds a colorful focal point. Natural light floods in through large windows, highlighting the open layout.

Condo in Orlando

4.97 out of 5 average rating, 144 reviews

Downtown Condo w/ Treetop Views & Free EV Charging

A vibrant living area features a Super Mario-themed mural depicting iconic characters against a blue backdrop. Plush seating surrounds a coffee table styled with bright colors, while a playful rug showcases a character from the Mario universe, creating a fun and inviting atmosphere for relaxation and gaming.

Condo in Orlando

4.93 out of 5 average rating, 116 reviews

Super Mario's Sky Suite - Epic Universe 3 BD SUITE

A spacious studio features a king-sized bed adorned with soft linens. A round dining table with stylish blue chairs is positioned nearby, alongside a vibrant decorative rug. Large windows provide natural light, framed by flowing gray curtains, while a modern chandelier hangs above, enhancing the elegant decor.

Condo in Orlando

4.88 out of 5 average rating, 232 reviews

Maria Luz Studio-Huge Terrace/Universal area.

A modern kitchen and dining area is showcased, featuring stainless steel appliances and dark cabinetry. A wooden dining table is set with blue chairs, providing ample seating. Large windows allow natural light to brighten the space, with a cozy living area visible in the background.

Condo in Orlando

4.91 out of 5 average rating, 121 reviews

VCR4-403 Deluxe New Apartment - Convention Center

A bright bedroom is presented, featuring a spacious bed with crisp white linens and a decorative orange pillow. Soft overhead lighting highlights the warm tones of the wooden headboard. The room includes an ensuite bathroom, visible through an open door, enhancing accessibility.

Condo in Orlando

4.88 out of 5 average rating, 148 reviews

Westgate Palace Resort 2 bedroom

Top guest favorite

A modern living area features a large sectional sofa and a glass coffee table. Natural light floods the space through multiple windows, enhancing the warm wooden flooring. A round dining table is set for four, while a decorative artwork piece adorns the wall.

Condo in Orlando

4.86 out of 5 average rating, 147 reviews

Beautiful Downtown Condo 1/1

Top guest favorite

The living area is furnished with a blue couch adorned with patterned pillows. Two matching wooden side tables with lamps provide soft lighting, while a wooden coffee table sits in the center. A decorative wall piece featuring palm trees adds a touch of character to the room.

Condo in Orlando

5 out of 5 average rating, 145 reviews

Disney & Epic Free Shuttle, Kitchen

The master bedroom suite is spacious and features a king size bed adorned with blue and white accents. Two lamps are positioned on each side of the bed, with artwork displayed above. Natural light enters through the window, and a private bathroom can be seen through the open door.

Condo in Orlando

4.96 out of 5 average rating, 181 reviews

Luxury 2B2B APT Near Convention Center, Universal

Family-friendly house rentals

A well-maintained exterior of a single-story home is presented, featuring a light yellow facade and a welcoming front porch. Lush greenery and palm trees are positioned along the pathway, with a manicured lawn and trimmed shrubbery enhancing the curb appeal.

Home in The Villages

4.95 out of 5 average rating, 128 reviews

2/2 custom pool home with 4 person gas golf cart

A circular fire pit area is surrounded by six blue adirondack chairs, set on a stone patio. Lush greenery and colorful plants frame the space, with a view of the house and pool area in the background. Sunlight brightens the inviting outdoor gathering spot.

Home in Clermont

4.92 out of 5 average rating, 116 reviews

Spacious Bungalow with Private Pool and Courtyard

Top guest favorite

The exterior of the home features a welcoming front entrance with a gray door and arched window. The pathway is lined with colorful foliage, and tropical plants surround the entrance. A lamp post stands at the forefront, providing soft illumination amidst the lush greenery.

Home in Sanford

4.97 out of 5 average rating, 259 reviews

Clean, cozy home in a GREAT location

A spacious master bedroom features a king-sized memory foam bed, dressed in a vibrant blue quilt. A mirrored stand, nightstands with lamps, and a plush bench provide functional accents. Natural light enters through room darkening blinds, enhancing the tranquil ambiance.

Home in Inverness

4.85 out of 5 average rating, 126 reviews

POOL Home near Racetrack, Downtown & Trail

A charming home is presented with a light blue exterior and a welcoming front porch. Lush greenery and potted plants adorn the entrance, while an inviting pathway leads to the front door. A single-car garage is visible to the right, framed by trees and bright skies.

Home in Mount Dora

5 out of 5 average rating, 169 reviews

UPSCALE DOWNTOWN VINTAGE 3/2 HOME

A well-maintained retreat home is set against a lush green landscape. A spacious back patio is visible, surrounded by trees, offering a fire pit area and outdoor seating. A wooden pathway leads through the grass, inviting guests to explore the serene surroundings.

Home in Sorrento

4.9 out of 5 average rating, 178 reviews

Wekiva Riverfront Home with Dock Close to Springs!

A spacious living area features a large sectional sofa facing a wooden entertainment unit with a television. Natural light enters through window treatments, illuminating the room. Two comfortable armchairs are arranged around a circular coffee table, with views of the surrounding park visible through the windows.

4.94 out of 5 average rating, 194 reviews

Wekiva Springs 5br 4 ba, spacious & lovely home

The light-filled living room features a stylish gray sofa, wooden side tables, and a coffee table. Natural light enters through the large window, illuminated by soft curtains. Decorative plants enhance the inviting ambiance, complemented by warm wooden flooring.

Home in Orlando

4.92 out of 5 average rating, 106 reviews

Charming 2BR Cottage, Downtown Orlando

Apartment rentals with air conditioning

A spacious sleeping area features a large bed centered on a neutral carpet. A light area rug is placed beneath the bed. Simple furniture includes a white table and two chairs, along with a TV stand. Natural light filters through sheer curtains.

Apartment in Ocoee

4.96 out of 5 average rating, 117 reviews

Completely Private and Cozy Studio

A game room is visible, featuring a billiard table with a black felt surface. In the background, a kitchen is seen with light wooden cabinetry and stainless steel appliances. Bar stools are positioned at a counter, enhancing the communal space.

Apartment in Sorrento

4.93 out of 5 average rating, 346 reviews

Quiet Neighborhood in the Country

A wooden dock extends into a calm lake, surrounded by gentle ripples and tall grasses. The sky is partially cloudy, with patches of blue visible. Trees frame the edges of the dock, contributing to the serene lakeside setting.

Apartment in Leesburg

4.95 out of 5 average rating, 21 reviews

Paradise on Lake Harris Apt #102

An open living room and kitchen area features comfortable seating on a dark sofa and a modern futon. A light fixture adds illumination to the space. A well-equipped kitchen is visible in the background, with wood cabinetry and a dining area near a window.

Apartment in Clermont

4.94 out of 5 average rating, 70 reviews

Relaxing 1-Bedroom Farm Retreat. Pets welcome!

Top guest favorite

A spacious living area features a sectional sofa and a round coffee table, complemented by soft lighting. A television is placed on a low cabinet, while decorative plants and a wall art piece add visual interest. Natural light enters through a window, enhancing the inviting atmosphere.

Apartment in Winter Garden

4.91 out of 5 average rating, 149 reviews

Stay A While

The bedroom features a spacious bed adorned with soft pillows and a textured throw blanket. Flanking nightstands hold stylish lamps, providing gentle lighting. A framed landscape image above the bed complements the neutral color scheme, and doorways to additional spaces are visible in the background.

Apartment in Clermont

4.79 out of 5 average rating, 277 reviews

Charming Lakefront Apt. Near Disney

Top guest favorite

A comfortable living area features a spacious couch with reclining sections and soft cushions. A Smart TV is placed on a black media console next to a stylish clock, while light filters through striped curtains. A small table holds a notepad, providing additional convenience.

Apartment in Minneola

4.96 out of 5 average rating, 114 reviews

Spacious Apartment In Minneola

Top guest favorite

The living area features a light-colored sofa and two patterned armchairs arranged around a small coffee table. Natural light fills the space through multiple windows, with a television placed on a dark wood console. Framed artwork adorns the walls, adding visual interest.

Apartment in Windermere

4.99 out of 5 average rating, 108 reviews

Relaxing 2BR Lakeview Retreat Close to Attractions

Other great vacation rentals near Leesburg

The villa's exterior is showcased against a vibrant sunset, featuring well-maintained landscaping with lush green grass and floral accents. The structure includes large windows and a welcoming front entrance, illuminated by soft outdoor lighting.

Villa in The Villages

5 out of 5 average rating, 8 reviews

Sunny Sky's Paradise w/Golf Cart

Top guest favorite

A spacious living area is presented, featuring a light-colored sofa paired with white accent tables. A ceiling fan above enhances airflow, and modern kitchen appliances are visible in the background. Natural light floods the space, highlighting the hardwood flooring and simple decorative touches.

Home in The Villages

5 out of 5 average rating, 13 reviews

Bay Breeze Villa

Top guest favorite

A single-story vacation home is presented with a light exterior and a neatly maintained front yard. A white picket fence encloses colorful landscaping, while a spacious driveway leads to a two-car garage. Clear skies enhance the inviting curb appeal of the property.

Home in Wildwood

5 out of 5 average rating, 14 reviews

Opal Oasis in The Villages

Top guest favorite

A single-story house features a white exterior with a gabled roof and a two-car garage. A white picket fence and manicured shrubs border the front yard, while a concrete driveway provides ample parking space. Clear blue skies are visible in the background.

Home in Wildwood

4.97 out of 5 average rating, 73 reviews

New home in the new part of the villages.

Top guest favorite

A red golf cart is parked in a spacious garage with a concrete floor. Bright natural light enters through the open garage door, illuminating the surroundings. A ceiling-mounted lift for additional storage is visible above, providing practical use of space.

Home in Sumterville

5 out of 5 average rating, 14 reviews

The Golfer's Edge

A dining area is presented with a dark wooden table surrounded by gray upholstered chairs. A rustic bench sits alongside. A unique woven light fixture hangs above, casting a warm glow. The walls are accented with a vibrant green panel, enhancing the space's natural feel.

Home in Leesburg

4.81 out of 5 average rating, 67 reviews

Eden’s Secret Garden Near Lake Harris

A community sign for The Village of Dabney is displayed prominently, surrounded by vibrant flowerbeds featuring seasonal blooms in varying colors. The sky appears clear with scattered clouds, providing a bright backdrop to the welcoming entrance.

Home in The Villages

4.83 out of 5 average rating, 6 reviews

Cozy Village Escape in Dabney

Top guest favorite

A single-story home is showcased with a well-maintained front yard, featuring manicured grass and small landscaping elements. The exterior is designed with a light-colored facade, and large windows reflect the evening sky's hues. A two-car garage is included, along with a spacious driveway.

Home in The Villages

5 out of 5 average rating, 15 reviews

BrandX Premium - 1921 McMurtrie

Destinations to explore