
Holiday rentals with a pool in Leesburg
Find and book unique homes with a pool on Airbnb
Top-rated rentals with a pool in Leesburg
Guests agree: These homes with a pool are highly rated for location, cleanliness and more.

2/2 custom pool home with 4 person gas golf cart
Beautiful Monterey style 1600 SQFT home, 2BR/2BA, fully furnished with a heated pool at 85' year round. Great location in Rio Grande; just a short golf cart ride to Spanish Springs & Lake Sumter. Home is on a quiet cul-de-sac; no neighbors behind. Private lanai from the Florida room. Tile and granite countertops throughout; Stainless steel appliances; sleeper sofa in the LR. 4 person gas golf cart also included. Sorry, hot tub not included. Dog friendly! Smart Tvs in both BRs, cable in LR only

Entire Home with an Office in Fenney
Furnished for the ultimate in guest comfort, entertainment & working online. Accommodates maximum of 2 guests who plan to sleep in the same bed. Only 1 bed provided. Bright office with large desk, TV, printer Furnishings are modern & luxurious, making you feel right at home. Fast Internet & YouTube TV Fully stocked kitchen Coffee & tea is complimentary Filtered home water system Please NON-smokers ONLY welcome NO pets Not suited for children Fees reduced for 28+ days; ask for details

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

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.

BrandX Premium - 1921 McMurtrie
Escape to this Waterfront Home in The Villages – Golf Cart & Bikes Included! Indulge in comfort and breathtaking views at this stunning getaway! ✔ 3 Bedrooms, 2 Bathrooms, 1 Sofa Sleeper ✔ Master Suite & Guest Rooms ✔ Office Space for Remote Work ✔ Open Living Area & Great Room ✔ Fully Equipped Kitchen & Full Laundry ✔ Waterfront Lanai w/ Unmatched Views ✔ Outdoor Patio with Dining Space ✔ Golf Cart & Bicycles Included ✔ Close to Golf Courses & Town Squares Book your luxury escape today!

2/2 Villa in Citrus Grove - Rates Reduced!
*Redone in 2023* - Brand new furniture throughout - Freshly painted - Screened in Lanai 2 Bedroom, 2 Bath located in Citrus Grove in The Villages, FL Great Location! - Very close to Citrus Grove adult pool - Homestead recreation center with family pool 0.7mi - Ezell Recreation Center 1.1mi - Sawgrass Complex 1.3mi There are several amenities for you to enjoy in The Villages - restaurants, bars, nightly live entertainment, shopping, golf, pickleball, shuffleboard, and so much more!

Location Can’t be Beat! With cart!
Experience The Village's retirement community lifestyle! The patio villa is located near Spanish Springs Town Square and the shopping corridor, where you will find nightly entertainment, dining and shopping. Walk to Savannah Center & Glenview Country Club. Your rental includes the complimentary use of a Yamaha gas golf cart and Guest ID cards that provide you access to our recreation facilities. Monthly guests may purchase Resident ID cards ($50) that include free executive golf.

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.

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.

Spacious Bungalow with Private Pool and Courtyard
Whether you seek relaxation or adventure, this house offers the best of both worlds! Relax in this spacious bungalow with a private courtyard, pool, hot tub, and fire pit! Take a short walk to downtown Clermont and discover the charming shops, restaurants, and breweries! Explore the sights and attractions that Central Florida has to offer! Whether you crave the vibrancy of downtown or the tranquility of your own oasis, this property offers the best of both worlds!

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.
Popular amenities for Leesburg rentals with a pool
House rentals with a pool

The Silver Lake Estate

3 BR 2 Bath Home Full Kitchen Pool Boat Parking

the villages Florida

Welcome to the Villages

King Bed, Small Dogs OK, and 4-Seater Golf Cart!

Luxury home with a pool and 3 bedroom

Brownwood Square - Villages Home

Serenity - In The Villages
Condo rentals with a pool

Luxury Condo On I-Drive & One Mile from Universal

Lovely Winter Park Home close to Hospitals !

Bahama Bay luxury resort, minutes to disney.

Near Disney/Universal Lovely 2bedroom/2bath Condo

Suites at Lake Buena Vista close Disney Spring A2

Maria Luz Studio-Huge Terrace/Universal area.

The Point Hotel & Suites - 705H Luxury - Pool View

3150-303 Condo Resort Water Park Pools near Disney
Other holiday rentals with a pool

On The Links-4bd w/pool in Spanish Springs!

Spotless Villa Near Brownwood Sq- Lanai & King Ste

The Villages, De La Vista West 1762

Heated Pool Golf Cart Dog Friendly in The Villages

The Sunshine Retreat with Golf Car

Boat Friendly & Private Pool Near The Villages

Pool and Spa Luxury Retreat

New! Resort Style Oasis ~ Heated Pool & Game Room
When is the best time to visit Leesburg?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $222 AUD | $243 AUD | $219 AUD | $183 AUD | $168 AUD | $161 AUD | $168 AUD | $156 AUD | $173 AUD | $183 AUD | $183 AUD | $186 AUD |
| 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 |
Quick stats about holiday rentals with a pool in Leesburg

Total holiday rentals
Explore 60 holiday rentals in Leesburg

Nightly prices starting at
Leesburg holiday rentals start at $44 AUD per night before taxes and fees

Verified guest reviews
Over 1,630 verified reviews to help you choose

Family-friendly holiday rentals
50 properties offer extra space and kid-friendly amenities

Pet-friendly accommodation
Find 20 rentals that welcome pets

Rentals with dedicated workspaces
30 properties have a dedicated workspace

Wi-Fi availability
60 of Leesburg holiday rentals include Wi-Fi access

Popular amenities for guests
Guests love Kitchen, Wi-Fi and Pool 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
- Universal Orlando Resort
- Give Kids the World Village
- Walt Disney World Resort Golf
- Disney Springs
- SeaWorld Orlando
- Orlando / Kissimmee KOA
- Discovery Cove
- Magic Kingdom Park
- ESPN Wide World of Sports
- Disney's Animal Kingdom Theme Park
- Epcot
- Old Town
- Kia Center
- Reunion Resort Golf Courses - Palmer & Watson
- Weeki Wachee Springs
- Universal's Volcano Bay
- Aquatica
- Bluegreen Vacations Fountains, Ascend Resort Collection
- Disney's Hollywood Studios
- Island H2O Live!
- ICON Park
- Southern Dunes Golf and Country Club




