
Vacation 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.

The Silver Lake Estate
“This is the best home we have ever rented!!!l” - 2023 guest. “We had a fabulous time at this ultra-luxurious home.” 2023 guest “Extremely accommodating hosts.” 2023 guest. “So Child and Infant friendly!” “playground and child gates.” Guest. A breathtaking lake-front Georgian-style mansion with a heated commercial-sized pool; game room; four master suites; and, dozens of charming and magical features. A tranquil and private setting, yet conveniently located to all central FL has to offer.

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

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

Palm Tree Pad 3BR The Villages| Golfcart| Kingbed
We assure you of a relaxing stay in our BRAND-NEW home, situated just minutes from the best town squares in The Villages! With a four-seater electric GOLFCART and NEW AMENITIES, you will be minutes from Eastport Town Square, Saluki Recreational Center, Brownwood Paddock and top courses like Southern Oaks, Jubilee, Mickylee, Belle Glade, Red Fox & Grey Fox,etc. You'll also be minutes away from Alden Bungalows pool. Please be advised that a $50 charge is applicable to get the lifestyle IDs.

Pool + Heated spa Family friendly King suite Oasis
Welcome to your perfect Florida getaway! This beautifully updated 3-bedroom, 2-bath home in Minneola offers everything you need for a relaxing and fun-filled stay. Whether you're traveling with family, friends, or pets, this home is designed to make you feel right at home. Step outside to your private backyard oasis featuring a sparkling pool, hot tub, and serene views overlooking a peaceful pond. Fire up the grill, unwind under the market lights, or soak up the sun with your favorite drink.

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.

The Sunshine Retreat with Golf Car
Come and enjoy this beautiful 2 Bed/2 Bath Patio Villa Home. We have made it very relaxing and welcoming for your stay. You will enjoy just a 3 minute golf car ride to Sawgrass, 15 minute golf car ride to new Eastport and a 20 min ride to Brownwood. It’s only a 5 minute walk to the pool and Aviary rec center is about a 5 minute golf car ride away. Golf Car included with home. Renter assumes all liability and will be responsible for any damage or injury caused by the use of the golf car.

New Luxury Home-Pool-Waterfront View-3 King Suites
Enjoy this unique, tranquil getaway in a new 2023 home less than 3 miles from Sawgrass Grove (nightly entertainment, restaurants), and only a few blocks from Mickylee Pitch and Putt, Jubilee Putting Course, and the new Franklin Recreation Center. Ezell, Homestead, and Citrus Grove Rec Centers are all under 3 miles away. Back yard with lanai, pool with fountain, pond, and trees is a RARE find in The Villages! 3 king bedroom suites! Golf cart (4 seats) available for an additional fee.

Entire private home/heatedpool/boat or rv parking
3 bedroom 2 bath spacious private home with heated pool. Conveniently located. Just a few minutes away from grocery stores, bars/restaurants, malls, movie theater, basically everything you need and more! 5 min to world famous fishing on Harris Chain of Lakes! 15min to downtown Mount Dora. 50min to Orlando and all its theme parks (Disney world, Seaworld, etc) Why pay top rates at cramped hotels when you can book your own spacious private home with us? Save, be comfortable and book today!

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.

Spacious Getaway ~ Heated LED Pool & Ping Pong
Welcome to your Spacious Getaway! Exterior Features: ★ LED Lights in Pool and on Pool Cage ★ Fenced-in yard & Fire-pit ★ Doorbell & Driveway Camera for safety Interior Features: ★ Ping Pong Table ★Large Shower in Master Bathroom ★ROKU on each TV Extras: ★ Heated Pool up to 95 Degrees - $40 per day (Pool Water is normally at 75 degrees without the Pool Heater) ⚠️ Pet-Friendly, but the pet must be added to the reservation ($75 Pet fee)⚠️ {Willing to Negotiate Monthly Prices}
Popular amenities for Leesburg rentals with a pool
House rentals with a pool

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Perfect home-families/friends in The Villages, FL!

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Condo rentals with a pool

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SL106 - Modern Condo - Resort Access included

Lakefront Resort Condo near Disney and Universal

Island Style at Bahama Bay - Minutes to Disney!

3171-206 Resort Lake View Disney Universal Orlando
Home rentals with a private pool

Wr001or (1stfororlando)

Disney's Championsgate: Private Pool & Arcade Fun!

Airy, Stylish Home with Pool Heat Included in Davenport

Visit Disney World from a Sunny Home with a Pool

Champions Gate 6bed 5bath Vacation Home

The Manors at Westridge Home W/ Private Pool

732bd 4 Bedroom Villa

1589mvd-The Retreat at Championsgate
When is the best time to visit Leesburg?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | ﺩ.ﺇ558 | ﺩ.ﺇ610 | ﺩ.ﺇ551 | ﺩ.ﺇ459 | ﺩ.ﺇ422 | ﺩ.ﺇ404 | ﺩ.ﺇ422 | ﺩ.ﺇ393 | ﺩ.ﺇ433 | ﺩ.ﺇ459 | ﺩ.ﺇ459 | ﺩ.ﺇ466 |
| 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 vacation rentals with a pool in Leesburg

Total vacation rentals
Explore 60 vacation rentals in Leesburg

Nightly prices starting at
Leesburg vacation rentals start at ﺩ.ﺇ110 per night before taxes and fees

Verified guest reviews
Over 1,570 verified reviews to help you choose

Family-friendly vacation rentals
50 properties offer extra space & kid-friendly amenities

Pet-friendly vacation rentals
Find 20 rentals that welcome pets

Rentals with dedicated workspaces
30 properties have a dedicated workspace

Wi-Fi availability
60 of Leesburg vacation rentals include wi-fi access

Popular amenities for guests
Guests love Kitchen, Wifi, and Pool across Leesburg rentals

4.8 Average rating
Leesburg stays are highly rated by guests—averaging 4.8 out of 5!
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- Universal Studios Florida
- Orange County Convention Center
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- Disney Springs
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- Magic Kingdom Park
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