
Vacation rentals with a pool in Lady Lake
Find and book unique homes with a pool on Airbnb
Top-rated rentals with a pool in Lady Lake
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

Ranch Retreat~10 beds~New
This ranch retreat home is perfect for large groups with plenty of parking. Perfect for celebrations, family gatherings, and even corporate or church events. Located on a large parcel of land in Lady Lake, FL, this home offers a quiet and secluded location that is centrally situated near the Villages and Chain of Lakes. We are 5 minutes away from Lake Griffin boat ramp, minutes away from Lake Griffin State Park, within 15 minutes of Venetian Gardens/Ski Beach and Lake Harris, and Eatons Beach.

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

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.

Pool, golf cart, private backyard. Paradise!
Come and enjoy this relaxing piece of paradise surrounded by lush greenery with your own, small, private pool (not heated). "Serene on the Green" is a beautifully remodeled 3 bedroom, 2 bathroom designer home (1,536 sqft) with a large screened outdoor pool area with lots of privacy. Our location 320 steps from the Santiago Recreation Complex with two golf courses and a short ride to Lake Sumter Landing and Spanish Springs is perfect. A new custom 2021 Yamaha QuieTech golf cart is included!

Villages Luxury Living~Heated Pool & Golf Cart
Home in the heart of The Villages with Heated Pool (if weather permits) and Golf Cart. The home is located 1.3mi from Spanish Springs Town Square and 2.9 mi from Lake Sumter Landing. A 7 minute golf cart ride from Spanish Springs Square, 15 minutes from Sumter Landing, 30 minutes from Brownsville Square. 200 Community pools some for adults only and some for families. 13 Recreation Centers 3 Old Fashion Town Squares with nightly Live entertainment 44 Golf Courses Plenty of Fun for All

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!

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.

The Villages Oasis
Welcome to The Villages Oasis! This charming villa offers a relaxing getaway with its private pool and hot tub. Enjoy comfortable accommodations with two bedrooms, a fully equipped kitchen, and convenient amenities like air conditioning and Wi-Fi. Located on Morse Road just a 5 minute drive from Spanish Springs, you'll have easy access, shopping, and more. Enjoy the perfect blend of relaxation and recreation in this beautiful Florida retreat.

Lake Sumter 2/2 Villa FREE gas cart/Pet friendly
Super clean 2-bed/2-bath property in Buttonwood with free use of gas cart. Nicely furnished, with washer/dryer, smart tv and vaulted ceilings. This patio villa is in a highly desirable area within walking distance to the Fishhawk pool, rec center and many golf courses. Equal distance between Lake Sumter Landing & Brownwood squares. $89 pet fee. 4 person cart available at $50/day. 2 person cart is free. Return cart full please.
Popular amenities for Lady Lake rentals with a pool
House rentals with a pool

Beautifully Furnished 3/2 with In-ground Pool

Oasis in Heart of The Villages

3 BR 2 BA Coastal-vibe,Golf Cart,Pools, Pickleball

Sunset Getaway - 3/2 dog friendly w/golf cart

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

Spotless 3BR Home w/ Golf Cart, Near Brownwood Sq

New Luxury Home-Pool-Waterfront View-3 King Suites

Outdoor Fun at the Pool + 2 Golf Carts!
Other vacation rentals with a pool

Villa la Bella

Heated Pool, Dog Friendly, Golf Cart Included

KingBed w/Cart

New home in the new part of the villages.

Luxury home with a pool and 3 bedroom

Pet Friendly in the Villages!

Newer Villa in The Villages near Brownwood

The Villages, Heated Pool Walk to Sawgrass
When is the best time to visit Lady Lake?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | ﺩ.ﺇ510 | ﺩ.ﺇ577 | ﺩ.ﺇ525 | ﺩ.ﺇ419 | ﺩ.ﺇ397 | ﺩ.ﺇ364 | ﺩ.ﺇ338 | ﺩ.ﺇ353 | ﺩ.ﺇ364 | ﺩ.ﺇ371 | ﺩ.ﺇ393 | ﺩ.ﺇ419 |
| 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 Lady Lake

Total vacation rentals
Explore 80 vacation rentals in Lady Lake

Nightly prices starting at
Lady Lake vacation rentals start at ﺩ.ﺇ220 per night before taxes and fees

Verified guest reviews
Over 1,020 verified reviews to help you choose

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

Pet-friendly vacation rentals
Find 50 rentals that welcome pets

Rentals with dedicated workspaces
40 properties have a dedicated workspace

Wi-Fi availability
80 of Lady Lake vacation rentals include wi-fi access

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

4.8 Average rating
Lady Lake stays are highly rated by guests—averaging 4.8 out of 5!
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