Pet-friendly holiday rentals in Leesburg

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

Getaway on the Waterway: Kayak, SUP, fish, relax!

Welcome to your peaceful Getaway on the Waterway right on the beautiful canal that connects Big and Little Lake Weir! Kick your feet up and wave at the boats going by as you grill or fish from the dock. Play a round of corn hole, hop on one of our paddleboards or kayaks for beautiful ride to either lake! Bring your boat/ jet ski or rent one from Eaton's Beach Aquatic sports, (they also offer sunset cruises and water taxi service to Eaton's Beach restaurant right from our dock!) RELAX and ENJOY!

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.

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

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.

Charming Mount Dora Cottage • Walk to Downtown

Walking distance to all Downtown Mount Dora has to offer! Our lovely 2 bedroom, 1 bath 1940s cottage has been recently renovated. Features fully outfitted kitchen, deck with gas grill and outdoor firepit. Comfortable and elegant living space with 65 inch smart TV. Primary bedroom features King bed and smart tv. Second bedroom has two cozy twin beds. Bikes available for use. Whether you’re coming to relax, boat, shop or partake in one of Mount Dora's many festivities, consider staying here!

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.

New Mid Century-Modern Studio

Enjoy your stay in this beautifully decorated studio with all the conveniences of home. The bed is Queen. We are located in College Park of Orlando. On Edgewater Drive there are restaurants, bars, and boutique shops. Close to downtown , 30 min. from all the attractions, and 5 min. from one of the city’s largest hospitals, 23 miles from ORMC airport. Walking distance from the historic Dubsdread Golf Club and restaurant. Pet fee required. Please make sure to add the pet to the reservation.

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!

Fabulous Courtyard Villa close to Sumter Landing

This home is the perfect vacation. When we saw this beautifully decorated villa, we felt like we were home. The exquisite landscaping was exactly what we have been looking for! The location is a mile from Sumter Landing and a stone's throw from the two pools, billiards, shuffleboard, pickleball, bocce ball. The best way to see it all is by the golf cart!!! The Villages has its own GPS for the Cart Paths. Schedule your stay and start packing your bags for an amazing experience.

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.

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.