
Holiday rentals in Leesburg
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Top-rated holiday rentals in Leesburg
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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.

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

Latitude Adjustment
Change your latitude in this beautiful two bedroom, two bathroom Patio Villa in The Villages. Located in the Village of Newell, this spacious and modern home has everything you need to make your stay relaxing and fun, including a golf cart! Enjoy a cup of coffee from the Keureg after your morning stroll on one of the nearby nature trails. Pools, pickleball and golf are all five minutes by golf cart, along with dining and entertainment at Sawgrass Grove and twelve minutes to the new Eastport!

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.

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!

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!

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.

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!

Cute & Cozy Tiny Guesthouse
Take it easy at this cozy and peaceful getaway located in a safe and quiet neighborhood near The Villages. It's conveniently located all within 1.5 miles to Walmart, Aldi, Waffle House, McDonald's, Pizza Hut, Cracker Barrel, BJ's Wholesale and many other shops and restaurants. Plus, The Villages Hospital. We are also located two miles from The Villages Spanish Springs town square which has free entertainment from 5pm to 9pm every night of the week.

New home in the new part of the villages.
Beautiful new home in the villages. All new appliances with all brand new furniture, beds and decor. You have quick access to Sawgrass grove Entertainment facility, Ezell recreation center and McGradys pub. This open floor plan with the kitchen opening to living room keeps everyone together. The huge island is a great hanging out spot. You will have access to many close by, pools, shuffle board, parks and golf courses during your stay.

Cozy Patio Villa (Newell)
Kick back and relax in this calm, stylish space. Indulge in this elegantly appointed 2 bedroom 2 bathroom lanai home. Fully furnished and ready for your family to enjoy everything the Villages has to offer. Our Brand New Patio Villa is located in the Village of Newell , only 2 miles away from Sawgrass/Ezell Recreation Center; 0.5 mile away from Franklin Recreation Center; 54 miles from MCO Orlando Airport, 48 miles from Disney.

Sunny Daze! Minutes to SawGrass
This home is minutes from Sawgrass Grove where you can Enjoy nightly entertainment. A short 2 minute Golf Cart ride to the Adult Pool,and the Golf Cart is included! 2 Bedrooms with King beds and a 3rd Bedroom with a twin bed and a work space. West Facing Lanai for early morning coffee and evening sunsets with a Glass of Wine! Big Screen Smart TV's, Grill, and everything you need to feel right at home.
Popular amenities for Leesburg holiday rentals
Other great holiday rentals in Leesburg

Bay Breeze Villa

2 min walk to pool, 4 seat cart, 5 min to Eastport

Opal Oasis in The Villages

Fam Fave in Fruitland 2nd fl 2bd,1ba kitch & loft

Newer Villa in The Villages near Brownwood

Charming Villages Retreat

Perfect Home in The Villages!

Delightful 2 bed/2 bath villa!
When is the best time to visit Leesburg?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | € 126 | € 125 | € 125 | € 109 | € 102 | € 93 | € 99 | € 96 | € 96 | € 97 | € 104 | € 106 |
| Avg. temp | 16°C | 18°C | 20°C | 22°C | 25°C | 27°C | 28°C | 28°C | 27°C | 24°C | 20°C | 17°C |
Frequently Asked Questions
Where should I stay in Leesburg?
Make yourself at home in Leesburg by choosing from our most frequently booked neighborhoods. We have over 680 vacation rentals in Fruitland Park, over 30 vacation rentals in Silver Lake, and over 130 vacation rentals in Lisbon.
Are there vacation rentals with a dedicated workspace in Leesburg?
Yes! Work meets play with ease at over 100 vacation rentals in Leesburg featuring dedicated workspaces. Stay connected and productive in your home away from home.
Are there pet-friendly vacation rentals in Leesburg?
Four-legged friends are welcome in Leesburg. Choose from more than 80 vacation rentals for guests traveling with pets.
Are there Leesburg vacation rentals on Airbnb with pools?
Yes! Dive into the perfect getaway at one of over 60 vacation homes with pools in Leesburg, available on Airbnb. Make a splash and soak up the sun in style!
How much does it cost to stay in apartment rentals in Leesburg?
Experience the best of Leesburg with our apartment rentals, starting at about $80 per day, before taxes and fees. Embrace comfort and style while staying within your budget in your home away from home.
Do house rentals in Leesburg have a gym?
Absolutely! We offer over 20 house rentals with a gym in Leesburg. Enjoy a tailored experience with all the comforts you desire.
Do house rentals in Leesburg have wifi?
Absolutely! We offer over 140 house rentals with wifi in Leesburg. Enjoy a tailored experience with all the comforts you desire.
Do house rentals in Leesburg have self check-in?
Absolutely! We offer over 10 house rentals with self check-in in Leesburg. Enjoy a tailored experience with all the comforts you desire.
Do house rentals in Leesburg have a bbq area?
Absolutely! We offer over 10 house rentals with a bbq area in Leesburg. Enjoy a tailored experience with all the comforts you desire.
Are there family-friendly vacation rentals in Leesburg?
Leesburg has more than 150 family-friendly stays. Amenities on the property may include high chairs, travel cribs, or strollers.
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 € 25 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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- Universal Studios Florida
- Orange County Convention Center
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