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Leesburg vacation rentals

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Top-rated vacation rentals in Leesburg

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

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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

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.

Guesthouse 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

Guesthouse 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.

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.

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

Guesthouse 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 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

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!

Guesthouse in Mount Dora

4.98 out of 5 average rating, 225 reviews

Cozy Buttercup Cottage!

Cozy 1/1 cottage- independent building, + nice breakfast kitchen, dining, & living room, great screened porch. 4 minutes 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!

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.

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.

Vacation rentals for every style

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Popular amenities for Leesburg vacation rentals

Laptop-friendly workspace

Stay near Leesburg's top sights

Yalaha Bakery20 locals recommend

Mission Inn Resort & Club12 locals recommend

Turners Kitchen + Bar10 locals recommend

Lake Square Mall10 locals recommend

Venetian Gardens Park9 locals recommend

Red Lobster8 locals recommend

Other great vacation rentals in Leesburg

Home in Lady Lake

5 out of 5 average rating, 6 reviews

Lakeside Retreat

Home in Lady Lake

4.94 out of 5 average rating, 78 reviews

Magnolia Cottage under the Paradise sun.

Home in The Villages

5 out of 5 average rating, 22 reviews

SpringHouse - 3 Bdrm Patio Villa in The Villages

Home in Tavares

4.96 out of 5 average rating, 24 reviews

Tavares Tropical Hideaway with Canal & Boat Slip

Rental unit in Tavares

5 out of 5 average rating, 28 reviews

The Emerald Fox Upstairs Apartment

Home in Leesburg

5 out of 5 average rating, 13 reviews

House on Harris Chain of Lakes

Home in Eustis

5 out of 5 average rating, 46 reviews

Porter's Porch

Guesthouse in Tavares

4.96 out of 5 average rating, 82 reviews

Peaceful, adorable, guest cottage on Apopka Canal.

Quick stats about vacation rentals in Leesburg

Total rentals
140 properties
Total number of reviews
2.7K reviews
Family-friendly rentals
110 properties are a good fit for families
Pet-friendly rentals
40 properties allow pets
Rentals with a pool
40 properties have a pool
Rentals with dedicated workspaces
60 properties have a dedicated workspace

Frequently Asked Questions

Are there vacation rentals with a dedicated workspace in Leesburg?
Yes! Work meets play with ease at over 60 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 40 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 40 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 villa rentals in Leesburg?
Experience the best of Leesburg with our villa rentals, starting at about $50 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 10 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 100 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 house rentals in Leesburg?
Leesburg has more than 90 family-friendly house rentals. Amenities on the property may include high chairs, travel cribs, or strollers.
What are the most popular amenities for House Rentals in Leesburg?
Enhance your stay in our House Rentals with the most popular amenities: over 10 homes with a gym, over 10 homes with a bbq area, over 100 homes with wifi, over 10 homes with self check-in, and more. Indulge in the ultimate retreat, tailored to your preferences.

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