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.

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Top guest favourite
A well-maintained exterior of a single-story home is presented, featuring a light yellow facade and a welcoming front porch. Lush greenery and palm trees are positioned along the pathway, with a manicured lawn and trimmed shrubbery enhancing the curb appeal.
Home in The Villages
4.96 out of 5 average rating, 141 reviews

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

Top guest favourite
Home in The Villages
5 out of 5 average rating, 18 reviews

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.

Top guest favourite
A sun-drenched pool area features a sparkling blue pool surrounded by comfortable seating. A table with an umbrella and colorful chairs offer space for relaxation. The sunroom with large windows provides views of the inviting outdoor space, enhancing the overall tranquil setting.
Home in Lady Lake
4.96 out of 5 average rating, 339 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.

Top guest favourite
The inviting exterior features a two-story home framed by lush green grass and mature trees. Arched windows and a symmetrical design enhance the charm, while a driveway leads to the front entrance, providing easy access to the peaceful surroundings.
Guest house in Silver Lake
4.98 out of 5 average rating, 425 reviews

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

Top guest favourite
A screened patio area is shown, featuring a private pool surrounded by an expansive deck. Comfortable seating arrangements are visible, along with lush plants and natural light streaming in from large windows overlooking the wooded landscape.
Guest house in Deer Island
4.96 out of 5 average rating, 136 reviews

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!

Guest favourite
A single-story home is situated on a corner lot, surrounded by well-maintained lawns and landscaping. Large trees provide shade, while the blue sky creates a bright backdrop. A screened-in porch and patio area are visible on the side of the house.
Home in The Villages
4.98 out of 5 average rating, 155 reviews

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.

Guest favourite
Home in Fruitland Park
4.93 out of 5 average rating, 46 reviews

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.

Superhost
A private pool area is featured with a clear blue pool and a built-in spa. Surrounding the pool, a spacious deck of pavers accommodates patio furniture and offers plenty of room for relaxation. Large sliding glass doors provide views of the interior sunroom.
Home in Leesburg
4.58 out of 5 average rating, 52 reviews

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.

Top guest favourite
The exterior of a single-story home is showcased, featuring a well-maintained front yard with greens and flowering shrubs. A paved driveway leads to a two-car garage, while the entrance is framed by neat landscaping. The sky above is clear and bright.
Home in The Villages
4.95 out of 5 average rating, 21 reviews

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.

Guest favourite
A spacious saltwater pool is enclosed by a screened area, surrounded by lush greenery and landscaping. Lounge chairs and a small jacuzzi can be seen along the poolside, with sunlight reflecting off the water's surface.
Home in Leesburg
4.93 out of 5 average rating, 58 reviews

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!

Top guest favourite
An inviting outdoor space features a spacious in-ground pool with a sunken hot tub nearby. The pool area is enclosed by a screened lanai, allowing for privacy. Light reflections dance on the water's surface, creating a peaceful ambiance.
Place to stay in The Villages
5 out of 5 average rating, 114 reviews

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!

Top guest favourite
The exterior of the villa is seen, featuring well-maintained landscaping with palm trees and neatly trimmed shrubs. A spacious driveway leads to the entrance, while a two-car garage is visible on the left. The sunlit facade showcases a welcoming atmosphere.
Home in The Villages
4.97 out of 5 average rating, 103 reviews

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

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Avg. price€ 132€ 144€ 130€ 108€ 100€ 95€ 100€ 93€ 102€ 108€ 112€ 121
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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 € 26 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 & child-friendly amenities

  • Pet-friendly holiday rentals

    Find 20 rentals that welcome pets

  • Rentals with dedicated workspaces

    30 properties have a dedicated workspace

  • Wifi availability

    60 of Leesburg holiday rentals include wifi 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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