Waterfront vacation rentals in Leesburg

4.95 out of 5 average rating, 133 reviews

A set of wooden steps leads up to a charming cottage nestled among trees. The entrance features large glass doors, inviting natural light into the space. The surrounding area is landscaped, enhancing the tranquil ambiance of the private property.

Cottage in Eustis

Redbird cottage and farm. Equestrian lake cottage

Step back into “Old Florida” charm at this updated 1968 lake cottage, on a 7-acre equestrian farm. Secluded from main roads yet just minutes from downtown Mount Dora and Eustis, this peaceful retreat offers the perfect blend of rustic serenity and comfort. Located on a lake that offers direct water access. Campfires are welcomed, and the tranquil setting is made even more magical by the sight of horses. Inside, you'll find cozy touches and comfortable furnishings, including pillow-top mattresses

Tiny home in Howey-in-the-Hills

A tiny home is showcased with a grey exterior and a metal roof. Two wooden chairs are positioned on a grassy area in front, and flower pots add color near the entrance. Steps lead up to the front porch, providing access to the inviting interior.

4.96 out of 5 average rating, 164 reviews

Horse Farm & (2) Tiny Homes to choose from

Rest & Relaxation at its finest! This Tiny Home is set to impress! Add on the natural beauty of the rolling hills of Howey, with some of Thee most impressive sunsets over the water & this becomes an Incredible Unique Stay! After sunset, enjoy a nice campfire in your firepit (wood avail) as you STARGAZE into the night! This Tiny Home is fully equipped with ALL of your needs. On the back 3 acres of property, from which you will have your own Golf Cart to travel to/from our Designate Parking Area.

4.97 out of 5 average rating, 154 reviews

The cabin is surrounded by lush greenery, positioned on a private peninsula. A spacious deck with seating faces the water, offering a serene view of the canal. Natural light filters through the trees, illuminating the inviting structure.

Cabin in Floral City

Private Waterfront Cabin Retreat with Kayaking

Your private retreat on an acre nestled on a canal to the Withlacoochee River, wrapping around 2 sides of the property. Relax on your porch overlooking the water as you watch the birds and deer play. Kids will love the tire swing, toys such as Lego, Lincoln logs, pool table and ski ball. Kayaks available to our guests awaiting adventure. Bond around the fire pit, walk the trails, lounge in the hammocks, and fish on the dock. Setup the big screen to watch a movie. Welcome to your get-a-way!

Guesthouse in Deer Island

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.

4.95 out of 5 average rating, 132 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.

4.97 out of 5 average rating, 414 reviews

A private balcony offers serene views of Lake Bryan and a swimming pool area. A small round table with two chairs invites relaxation, while warm colors from the sunset enhance the tranquil setting. Lush trees frame the scene, creating a peaceful atmosphere.

Condo in Orlando

Waterfront Condo minutes to Disney & Universal

Just minutes from Disney World and Universal Studios, this condo places you in the heart of Orlando’s top attractions, including Disney Springs, Islands of Adventure, SeaWorld, Magic Kingdom, Epcot, two outlet malls, and more. Relax on your private balcony with breathtaking views of Lake Bryan, or enjoy the resort-style pool with a full Tiki bar and dining menu. Additional perks include free parking, 24-hour security, and complimentary HBO & Netflix. No deposit required and no extra fees.

4.97 out of 5 average rating, 179 reviews

A spacious wooden dock extends over the calm waters, surrounded by lush greenery. Several people are seated, enjoying a meal together. Lawn chairs are arranged comfortably, with trees reflecting off the clear surface of the water nearby, creating a serene atmosphere.

Home in Weirsdale

Beautiful House On the River, Kayaks, Large Dock!

Come relax by the river in this 3-bedroom, 2-bathroom vacation rental in Lady Lake, Florida. Recently built by our family in 2022, the home has a screened in back porch, a fire pit, WIFI, and is complete with a large private dock right on the Ocklawaha River. All that and it's located only 10 minutes from The Villages where you can shop and have fun. Centrally located 1-1/2 hours from Disney, Daytona beach, and Tampa. Lockbox key access is available for check-ins at any time of day.

4.91 out of 5 average rating, 113 reviews

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

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!

4.98 out of 5 average rating, 159 reviews

A wooden dock extends into a calm pond, reflecting the blue sky and fluffy white clouds above. Lush greenery borders the water, creating a tranquil natural setting. A small boat is anchored nearby, adding to the serene atmosphere.

Guest suite in Umatilla

Completely Private Suite w/ Pond, Grill & Kayak

Conveniently located in Lake County, FL, you are about an hour from beaches, theme parks and the Orlando airport, yet only minutes from the Ocala National Forest and beautiful natural springs. We have an abundance of wildlife here: birds, gators, bears, lizards. and more. Smoking is allowed but outside only. Our place is best suited for couples or solo travelers. We have a two person max limit. No kids. No extra guests. No parties are allowed on our property. Pet's are welcomed

4.87 out of 5 average rating, 342 reviews

A covered porch is showcased, adorned with climbing plants and vibrant foliage. Two sets of double doors lead into the cottage. A mix of potted plants and outdoor seating arrangements provides a welcoming atmosphere, inviting guests to enjoy the surrounding natural beauty.

Guesthouse in Mount Dora

A Lakeshore Cottage vintage 1926

What's new for 2019 a brand new dock and fishing pier. Additional boat docking available. Brand new Central Cold & Dependable Air Condition- Brand new 8 foot tall privacy fence & gate, parking pad beside cottage. -Eco Smart: lock, cork floors, instant hot H2O, solar lighting, copper sink, antiques, refurbished architecture ,charming! 2 nights/festivals ABSOLUTE RESTRICTION to ANIMALS! NO EXCEPTIONS. DO NOT Instant book if you are with any animals. Sorry allergies don’t allow.

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.

4.9 out of 5 average rating, 155 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.

4.96 out of 5 average rating, 114 reviews

An open-concept living area features natural light streaming through large windows with scenic views of the lake. Cozy seating arrangements include a comfortable sectional and accent chairs, complemented by a dining space and a well-equipped kitchen with modern appliances.

Home in Tavares

Lake Dora Dream-Waterfront/Pool

Luxurious lakefront home on Lake Dora - 8 minutes to downtown Mount Dora and Tavares. Enjoy your vacation in this newly renovated pool home (Pool Not Heated) on Lake Dora and the Harris chain of Lakes. Bring your boat or rent one nearby to explore the area by water and cruise the Dora Canal to Lake Eustis. Included is a guest apartment with private entrance totaling 4 bedrooms and 4 full baths. Just a half mile to the Tavares Pavilion and dining in downtown Tavares.

4.98 out of 5 average rating, 126 reviews

The exterior of a two-story detached home is presented, featuring white siding and black shutters. The entrance is adorned with planters, and a small walkway leads to the front door. Lush greenery surrounds the property, and a clear blue sky is visible above.

Cottage in Umatilla

Cottage by the Lake

Cute, comfortable 1935 detached home which is 900 SQUARE FEET AND PET FRIENDLY. The other side of the property has our main home. The cottage is newly remodeled and fenced in. Views of Lake Umatilla from all rooms. 8 miles to beautiful Mount Dora and 3 miles to downtown Eustis. 1 hour to attractions, airport and east coast beaches. We are 20-30 minutes from most local Springs. Our Lake Umatilla does have public boat ramp access

Popular amenities for Leesburg waterfront rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Waterfront apartment rentals

4.84 out of 5 average rating, 152 reviews

A private terrace is presented with ample lounge chairs facing a scenic waterfront view. Lush greenery surrounds the area, and a bright blue sky is visible above, enhancing the open atmosphere. The cityscape with buildings is visible in the distance.

Apartment in Orlando

BEST Views~2B2B~Universal~Disney

Aerial view of a resort-style pool area, featuring winding lazy river and colorful waterslides. Surrounding palm trees and lounge chairs enhance the tropical ambiance. The nearby lake provides a scenic backdrop, while various guests can be seen enjoying the water attractions.

4.78 out of 5 average rating, 104 reviews

WinterWarmth+Family fun+Free Parking

4.99 out of 5 average rating, 121 reviews

Apartment in Orlando

Private Rooftop Suite! No resort fees!

A well-lit bedroom features a spacious bed with a white quilted cover and decorative pillows. A round mirror is mounted above a side table, complemented by wall art. The room is connected to another area visible through an open door.

4.93 out of 5 average rating, 217 reviews

Lovely one bedroom apartment.

4.88 out of 5 average rating, 166 reviews

Apartment in Orlando

Renovated Studio-Near INT'L Drive and Parks!

A large resort-style pool, shaped like a Mickey Mouse head, is surrounded by palm trees and lounge chairs. Guests are seen relaxing on sun loungers and enjoying the water, with umbrellas providing shade in certain areas. Additional smaller pools are visible nearby.

4.91 out of 5 average rating, 133 reviews

Amazing Apartment in Orlando - Kissimmee

A spacious balcony is equipped with woven seating and a glass-top table. Views of a tranquil waterway and lush greenery are visible, framed by modern railings. Soft clouds drift across the sky, enhancing the overall serene atmosphere of the outdoor space.

4.79 out of 5 average rating, 121 reviews

★BRAND NEW APT with LAKEVIEW - Close to Disney★

4.97 out of 5 average rating, 116 reviews

Premium LakeView/MoanaRoom/Walk to StoreyClubHouse

Waterfront house rentals

4.82 out of 5 average rating, 106 reviews

A single-story home is viewed from the street, featuring a covered front entrance and a large driveway. Lush green grass surrounds the property, with palm trees and other foliage enhancing the front yard. The home is enclosed by a privacy fence.

Home in Montverde

Private 3-bedroom pool & waterfront home

4.85 out of 5 average rating, 13 reviews

Home in Sumterville

Spacious 3BR in The Villages | King Bed | Golfcart

5 out of 5 average rating, 26 reviews

A vibrant sunset casts shades of orange and pink across the sky, with silhouettes of tall trees framing the scene. The tranquil waters of Lake Harris reflect the colorful hues, while marshy grass lines the shore, providing a peaceful natural setting.

Home in Tavares

Lake Harris Getaway

A Georgian-style mansion features a classic red brick exterior and large windows framed by manicured gardens. The expansive lawn offers lush greenery, while mature trees provide shaded areas. A winding driveway leads to the entrance, enhancing the home's charming presence in a tranquil setting.

5 out of 5 average rating, 14 reviews

The Silver Lake Estate

A modern two-story lakefront home features a light-colored exterior and a welcoming front porch. Neatly landscaped greenery lines the pathway, while large windows allow natural light into the interior. The garage door is visible, complementing the overall contemporary design.

5 out of 5 average rating, 30 reviews

Luxury Lakefront 4 bedroom house

4.97 out of 5 average rating, 100 reviews

Home in Clermont

Adorable Downtown Lakeview Home 1105

The living area features a modern couch accompanied by a navy armchair. A round coffee table sits in front, complemented by decorative throw pillows. The entryway leads to a well-equipped kitchen, where white cabinetry and clean countertops are visible, offering a bright and inviting environment.

4.81 out of 5 average rating, 73 reviews

Lake Eustis vacation home

4.8 out of 5 average rating, 5 reviews

Home in Fruitland Park

Lakeview+ Shuffleboard Table + Wildlife Spotting

Waterfront condo rentals

A family-friendly living area is presented with a large, comfortable sectional sofa facing a flat-screen TV. Adjacent, a vibrant children's bedroom features a whimsical Moana theme with a sandy beach mural, complemented by a canopy bed adorned with tropical accents. The ceiling displays playful elements, enhancing the kid-friendly atmosphere.

4.98 out of 5 average rating, 200 reviews

303_To Infinity & the Ocean Breeze Apartment

4.73 out of 5 average rating, 348 reviews

Downtown Orlando is depicted with its skyline in the background, framed by a tranquil lake. Three fountains create gentle sprays in the water, reflecting the vibrant blue sky. Lush trees line the water's edge, adding greenery to the urban landscape.

Condo in South Eola

Retro lake Eola 1 Bedroom Condo Thornton park

4.95 out of 5 average rating, 115 reviews

A bright living area features a cozy gray sofa paired with two stylish yellow chairs. A wooden coffee table sits atop a textured area rug, while large glass doors lead to a balcony that offers views of Lake Bryan.

Condo in Orlando

Modern Lake view Condo 1 mile from Disney

A modern living area features a cozy sofa facing a mounted TV, displaying a serene landscape. Behind the sofa, an electric fireplace adds ambiance. The open layout connects to a well-equipped kitchen, enhancing a sense of space within the inviting atmosphere. Accessibility to dining areas is evident.

4.91 out of 5 average rating, 155 reviews

Chic Disney Resort Condo • Pool Access Near Parks

The master bedroom features a spacious bed with a tufted headboard, complemented by a decorative mirror and framed artwork. Natural light streams in through a large window, revealing views of greenery. A warm color palette and wood accents create a relaxing atmosphere.

4.94 out of 5 average rating, 135 reviews

*NEW* Adventureland Stay / Sleeps 6 / Near Disney

4.83 out of 5 average rating, 160 reviews

A modern living area features a sleek black sectional sofa positioned alongside a minimalist coffee table. Above, three framed artworks add visual interest, while potted plants provide a touch of greenery. Natural light filters through vertical blinds, enhancing the bright and airy ambiance.

Condo in Orlando

Universal Studios Getaway – Prime Location!

An aerial view of a community pool area features a curvilinear swimming pool surrounded by lounge chairs and shaded seating areas. A hot tub is located adjacent to the pool, surrounded by lush landscaping and palm trees. The clubhouse is visible, contributing to the inviting atmosphere.

4.89 out of 5 average rating, 279 reviews

Marvelous apartment near Disney first floor

A modern living area features a plush blue sectional sofa complemented by two stylish lounge chairs. A light area rug sits under a chic coffee table, while large sliding glass doors provide a view of the outdoors and allow natural light to enhance the space.