
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.

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

Palm Tree Pad 3BR The Villages| Golfcart| Kingbed
Enjoy your stay in this brand-new home located just minutes from the best attractions in The Villages! With a 4-seater electric golf cart & brand-new amenities, you’ll be close to Eastport Town Sq, Saluki Recreation Center, Brownwood Paddock Square & top golf courses like Southern Oaks, Jubilee, Mickylee & Belle Glade. You’ll also be just minutes from the Alden Bungalows Pool Please be advised that a $50 charge is applicable to get the lifestyle IDs. There's also a $20 golfcart insurance fee.

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
Escape to Sapphire Cottage, a 5-acre wooded retreat with a private canal boat dock. Relax by the shared pool, fish from the dock, or enjoy a BBQ at the firepit. Our cozy cottage features a queen master, 2 sofa-beds, a full kitchen, and dining for 6. From meeting our farm animals, biking, kayaking, or reading in the gazebo, there is something for everyone! We live in the main house across the way and are happy to help while ensuring you have a peaceful stay. Come make lasting memories with us!

Whole House-sleeps 10 The Villages Spanish Springs
Live Music on the Square. Golf, Pools, tennis, etc. Entire house in the Village of Del Mar located within the exclusive gated community of The Villages, Florida! A three-bedroom, two-bathroom spacious home with a living room with a sleeper sofa, dining room, lanai and a patio with a grill. It is located on a corner lot, only an 8-minute walk (2 minutes by car or golf cart) to Spanish Springs Town Square and a short distance to three different executive golf courses and dozens of amenities.

Luxury home with a pool and 3 bedroom
Spacious water front home that sits on a beautiful freshwater canal with access to the great Lake Griffin. Offers a perfect blend of luxury & comfort, a perfect space for entertaining & relaxation. Escape the pressures of everyday life, enjoy the outdoors in style with the lanai in the rear of the home, perfect for barbecuing or lounging while enjoying the water view. Has access to onsite community boat ramp, campgrounds, nature trails, kayaking, major roads, stores, restaurants, and more.

3 BR 2 Bath Home Full Kitchen Pool Boat Parking
3 BR 2 Bath main section of a large property. Kitchen: granite countertops, breakfast bar, stainless-steel appliances. Florida room: Foosball table, views of the pool, backyard, screen porch. Parking pads, circle driveway, room for dozens of cars, RVs, or boats and trailers, no unhitching necessary. Caretaker on premises in a separate area isolated from main house, no interaction necessary. Close to lakes, Venetian Park, Downtown Leesburg, Mall. One hour from Disney. No pets. No Parties.

The Villages, Citrus Grove home away from home
Create great memories at this centrally-located home, with an open floor plan with vaulted ceilings. The kitchen is well equipped and the living room has a queen size sleeper sofa and a smart TV (internet/WIFI). The master bedroom has a king size bed, walk in closet, smart TV, master bathroom and a work area with a desk and printer. The guest bedroom has a queen size bed, large closet and smart TV. Both bedrooms have black out curtains and hair dryers, and linens. Grill/2 bikes incl.

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!

Safari themed private addition with pool/hot tub.
This special Guest house addition is close to everything in The Villages! Making it easy to plan your visit.! We are in The Village of Osceola Hills at Soaring Eagle Preserve. A short golf cart or car ride to Brownwood Square and Sumter Landing Square for dining, shopping, and dancing! A 5 min jaunt to two plazas for groceries, gas, and eating:-) Access to play over 50 golf courses at a minimal fee. Ask us about our easy 4 seater Golf-cart rental and upon request free Guest passes!

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

The Silver Lake Estate

Villages home with unique elevated front porch

5-Star Luxury | Prime Location & Top Amenities

The Promise Land~10 beds~New

Newer Villa in The Villages near Brownwood

The Villages, Heated Pool Walk to Sawgrass

Charming Villages Retreat

House on Golf Course, with Heated Pool & Golf Cart
Condo rentals with a pool

Lovely Winter Park Home close to Hospitals !

Super Mario's Sky Suite - Epic Universe 3 BD SUITE

Disney Area Updated Lakefront Resort Condo 2 POOLS

Westgate Palace Resort 2 bedroom

Waterfront Condo minutes to Disney & Universal

Fabulous condo-Bahama Bay Resort, Close to Disney

"Ocean's Gate" - 2BD/2BA condo near Disney

VISTA CAY RESORT, 2 BEDROOM STANDARD APARTMENT
Other vacation rentals with a pool

StJohns is a great area for golf, hiking, Kayaking

2 min walk to pool, 4 seat cart, 5 min to Eastport

Perfect location Lake Sumpter Villa w/ Golf Cart

Beautiful Sunsets/Pool/Dock on Lake Weir

Heated Pool Golf Cart Dog Friendly in The Villages

Unique cottage with a heated pool on the canal

The Sunshine Retreat with Golf Car

Newest Hotspot in The Villages Eastport/Middleton”
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.ﺇ474 | ﺩ.ﺇ514 |
| 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 1,630 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

4.9 Average rating
Leesburg stays are highly rated by guests—averaging 4.9 out of 5!
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- Universal Studios Florida
- Walt Disney World Resort
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- Orange County Convention Center
- Walt Disney World Resort Golf
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- SeaWorld Orlando
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- Orlando / Kissimmee KOA
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- ESPN Wide World of Sports
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