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

4.96 out of 5 average rating, 330 reviews

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

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.

4.95 out of 5 average rating, 157 reviews

The exterior of a single-story villa is depicted, featuring a light-colored stucco facade and a two-car garage. Paved driveway curves towards the entrance, with decorative landscaping including a potted plant and stone accents. Windows are adorned with decorative arches, enhancing curb appeal.

Home in The Villages

Remodeled 2/2 Baja style villa w/4 person cart

4 person, yamaha gas golfcart offered at this baja style 1000 sqft 2BR, 2BA courtyard villa! It comes fully furnished with pots, pans, linens, and does have a blow dryer and keurig! located in the De La Vista South area just off Morse, this villa is just a short cart ride to Spanish Springs or Sumter Landing. The villa has new stainless appliances, beautiful plank flooring, and fresh paint. King bed in the master, queen bed in the guest bedroom. All bedrooms have smart TV's, cable in LR only

4.98 out of 5 average rating, 417 reviews

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

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

5 out of 5 average rating, 18 reviews

Bungalow in Okahumpka

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!

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!

4.96 out of 5 average rating, 265 reviews

A cozy sleeping area is highlighted by two queen-size beds, each adorned with checkered yellow and white blankets. A lamp on a nightstand provides gentle illumination, and natural light filters through the window, which is fitted with blinds.

Guesthouse in Mount Dora

Cozy Buttercup Cottage!

Cozy 1/1 cottage- independent building, + nice breakfast kitchen, dining, & living room, great screened porch. 4 minute drive from Renninger’s, 5 minutes from Mount Dora City Hall Area where you'll find unique shops, restaurants, antiques, art museums, galleries, marina, parks, & many activities! *32 min/ Universal Studios & Island of Adventure, 43/ Magic Kingdom, 40 min/ Orlando Intl. Airport, 36 min/ Sanford-Orl Airport, 18 min/ Rock Spring, 48 min/ Silver Glenn Spring & much more!

Place to stay in The Villages

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.

5 out of 5 average rating, 103 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!

4.98 out of 5 average rating, 131 reviews

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

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!

4.89 out of 5 average rating, 162 reviews

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

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.

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.

4.95 out of 5 average rating, 110 reviews

A charming cottage is showcased, featuring a light-colored exterior with red shutters. The entrance is framed by a covered porch and planters, while a landscaped area with low shrubs and flowers adds a welcoming touch to the pathway.

Cottage in Eustis

Anneliese's Cottage

Just a delightful walk from Lake Eustis and its quaint downtown shopping & dining district, a 10 minute drive to Historic downtown Mt. Dora, and less than an hour from Orlando / Daytona Beach, this cottage , decorated with cozy elegance, is the perfect place to relax and truly enjoy all that the area has to offer. Right next door, you'll find an eclectic day spa, where you can set up a relaxing massage, facial, or have your hair & nails done during your stay!

Popular amenities for Leesburg vacation rentals

Self check-in

Gym

BBQ grill

Laptop-friendly workspace

Wifi

Boutique hotels in Leesburg

A large swimming pool is surrounded by tall palm trees and spacious buildings featuring colorful facades. Lounge chairs are arranged around the pool area, with umbrellas providing shade. Guests can be seen enjoying the water and relaxing in the inviting environment.

4.56 out of 5 average rating, 231 reviews

Beautiful apartament - Vacation Village at Parkway

Superhost

A large outdoor heated pool is surrounded by lounge chairs with red cushions and tables topped with red umbrellas. The hotel building features multiple levels with balconies overlooking the pool area, complemented by a clear blue sky.

Hotel room in Ocala

Equus Inn - Ocala's Only Boutique Hotel!

A modern sleeping area features a spacious bed with neutral bedding and decorative red accents. A minimalist table with two chairs is positioned nearby, alongside a standing lamp. A wall art piece adds a splash of color, while the light wood flooring enhances the bright atmosphere.

4.23 out of 5 average rating, 48 reviews

Hotel Room Very Good Location Disney W 10 Minutes

A fenced outdoor pool area features two colorful inflatable floats, a swan and a unicorn, floating on the clear water. Surrounding the pool are several lounge chairs, and the two-story building with balcony access is visible in the background.

4.88 out of 5 average rating, 287 reviews

Epic Place / Free Shuttle, Parking & WiFi

4.63 out of 5 average rating, 216 reviews

Beautiful room for 4 people con traslado

A series of multi-story buildings with warm-colored exteriors is set alongside a serene lake, reflecting the clear blue sky. Lush palm trees and greenery enhance the setting, providing a welcoming atmosphere near the water's edge.

Hotel room in Lake Buena Vista

4.89 out of 5 average rating, 9 reviews

Wyndham Bonnet Creek Resort

4.95 out of 5 average rating, 21 reviews

A spacious bedroom features a large bed with decorative bedding, accompanied by neatly stacked towels at its foot. Soft blue walls and a ceiling fan enhance the room's comfort. Natural light filters through a window, illuminating an inviting sitting area with a patterned ottoman.

Hotel room in Mount Dora

The Bamboo - Estate at Mt Dora

A cozy room is arranged with two spacious beds, each adorned with dark green bedding. Large wall art featuring greenery adds a natural touch, while a wooden desk and TV unit are positioned against one wall. Soft lighting enhances the welcoming ambiance.

4.71 out of 5 average rating, 76 reviews

Disney Retreat VIII

Other great vacation rentals in Leesburg

5 out of 5 average rating, 26 reviews

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

Treasure Island Getaway Kayak and Mini Golf

4.91 out of 5 average rating, 87 reviews

An enclosed pool area features a large, well-lit swimming pool with turquoise water. A water slide is positioned on one side, while the background showcases lounge seating and a bar area illuminated in soft blue light.

Guest suite in Leesburg

Mid Century Living on Lake Eustis. Dock available.

4.89 out of 5 average rating, 18 reviews

The kitchen features modern white cabinetry with silver handles, a stainless steel refrigerator, and an oven. A clock adorns the wall, while a small dining area is arranged on the side. Natural light is present, highlighting the clean countertops and open layout.

Apartment in Lady Lake

Snooky Park Apartment next to The Villages

4.8 out of 5 average rating, 20 reviews

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

Lakefront Magic Wilderness Cabin

4.97 out of 5 average rating, 33 reviews

Cabin in Mount Dora

Sunset Cottage & Lake Dora Dock

5 out of 5 average rating, 55 reviews

A compact living area features a light-colored sofa with decorative pillows. A small dining table and two chairs are positioned nearby. The kitchen is equipped with cabinets and appliances, and warm lighting creates an inviting atmosphere.

Apartment in Leesburg

Downtown Leesburg Owners Suite

4.93 out of 5 average rating, 84 reviews

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

Lakefront home chain of lakes & near Mount Dora