Holiday rentals in Leesburg

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Top-rated holiday rentals in Leesburg

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Guest favourite

Rental unit in Leesburg

5 out of 5 average rating, 28 reviews

Downtown Leesburg Owners Suite

Take it easy at this unique and tranquil getaway. Walk to downtown restaurants and festivities. Take a walk around the pond at Fountain Lake Park. Relax under a plush outdoor living space with provided grilling and dining area. NOT Lakefront, But This apartment is a short 1/2 block stroll from Downtown Leesburg, including Dining, Pubs, Shops and Craft Beer houses. Just a few blocks from Beacon College, UF Health Hospital, downtown entertainment and just a half mile walk to beautiful Lake Harris

Guest favourite

Home in Lady Lake

4.96 out of 5 average rating, 287 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.

Guest favourite

Guest house in Leesburg

4.98 out of 5 average rating, 363 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

Guest favourite

Guest house in Deer Island

4.94 out of 5 average rating, 101 reviews

Sapphire Cottage - sleeps 6, on 5 acres with canal

We are on 5 beautiful wooded acres with a boat dock on the canal. Relax by the 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 or a bit of adventure we have the perfect remote location for you. 2 kayaks, 2 bikes, & pontoon tours available…ask 4 details.

Guest favourite

Home in The Villages

4.95 out of 5 average rating, 150 reviews

Home away from home entire house

Located in an excellent area in the Chatham neighborhood, of the Bromley villas. This home offers easy access to restaurants, shopping and recreation. For nightly entertainment you're a short distance away from Lake Sumter land and Spanish Spring town Square where you will find many restaurants, grocery stores and free nightly live entertainment. This home is fully equipped with everything you need. Pets are allowed. Recreational guest passes included. Golf cart not included with reservation.

Guest favourite

Cottage in Coleman

4.97 out of 5 average rating, 116 reviews

Peaceful Chic Cottage Mini Farm Near The Villages

Perfect Getaway! Enjoy our clean, peaceful, chic tiny farmhouse located on our 1.5 acre homestead. This is the perfect location as we are 5 minutes from I75 and Florida Turnpike. We are 10 minutes from LIVE Music, Restaurants and more in the Brownwood Town Square. We offer free parking for 2 vehicles and welcome well behaved dogs. (Please let me know if you are bringing your furry friend) Looking forward to hosting you! 1 h. from Orlando/Disney & Tampa/Busch Gardens 25 m. Leesburg Hospital

Guest favourite

Guest house in Leesburg

4.88 out of 5 average rating, 42 reviews

Beautiful house 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.

Guest favourite

Guest suite in Umatilla

4.99 out of 5 average rating, 113 reviews

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

Guest favourite

Home in Eustis

4.89 out of 5 average rating, 118 reviews

House on Lake Eustis

Located in Eustis Florida. Next to the Lake Eustis Sailing Club, Small Lakefront house with 1 bedroom, 1 bathroom, Living Room, Full Kitchen, Small desk for working, Screened Porch with beautiful lake views. Close to restaurants, grocery stores, and parks. 10 minutes from Mount Dora, one hour from both the East and West coasts. One hour from Disney World and most attractions. 4.2 Miles or 10 minutes from Advent Health Waterman NOTE: NO ANIMALS OF ANY KIND ARE ALLOWED DUE TO ALLERGIES!

Guest favourite

Home in Leesburg

4.87 out of 5 average rating, 140 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.

Guest favourite

Barn in Leesburg

4.9 out of 5 average rating, 10 reviews

Dirty Dog Barndominium

Come and stay at this rustic designed Barndominium in the heart of Dirty Dog Organic Farm. You can hear the roosters crow, and watch the chickens in the morning while drinking your coffee outside. Help gather eggs and feed our pig a treat. This barn seems far away, yet is only 10 minutes to downtown Leesburg. Splash pad, public pools, hiking, boating and many other activities are a short drive. Come stay at the farm and leave all your stress behind.

Guest favourite

Cottage in Tavares

4.97 out of 5 average rating, 221 reviews

Lakeside Cottage on Lake Dora

A charming 1200 sq ft, two bedroom, two bath cottage located on beautiful Lake Dora with white sand beach. A great place to relax and your home away from home. Just minutes from Tavares (known as the Seaplane City) and Mt. Dora (known as the City of Festivals.) You can bring your boat and tie it up to the dock. Large circular drive with plenty of parking for cars, trailers, etc.