
Holiday 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

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.

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.

Heated Pool Golf Cart Dog Friendly in The Villages
Nestled amidst lush greenery ,Vida Rosa’s private pool provides a serene outdoor oasis, complete with a dining area, loungers, and a gas BBQ. The luxurious accommodations are thoughtfully designed to evoke a sense of calm and elegance. Conveniently located, just a short golf cart ride away from the squares of Spanish Springs & Lake Sumter offering a variety of entertainment etc. Note: The pool has a jet tub attached to it. The water temperature is the same temperature as the pool, 86 .

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!

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.

Perfect "get-away" home for a couple or family!
Great getaway for a single, couple, or a family. Only an hour from the Disney Parks! By golf cart, you are only minutes from pools, rec. centers, golf courses and many dining options as well as the grocery store. The home includes a nice outdoor seating area. The "squares" provide FREE nightly entertainment. I offer a golf cart for getting around in The Villages. This get-away home is perfect for people looking to relax OR never be bored! It's always a great day at The Villages!

Villages-Private Heated Pool-Central Location
Enjoy a stylish experience at this centrally located 3-bedroom home. 5-7 minutes golf cart ride from Sumter Landing, 15 minutes from Spanish Springs Square, 20 minutes from Brownsville Square. 200 Community pools some for adults only and some for families. 13 Recreation Centers with Pickle Ball, Shuffleboard, Billiards, Study groups, etc. 3 Old Fashion Town Squares with nightly Live entertainment. 44 Golf Courses

Briar Meadow Villa - Dogs are welcome!
Dogs are welcome in this nicely furnished Courtyard Villa, with a fenced in backyard. Near Nancy Lopez Legacy Golf & Country Club, Mulberry Grove Rec Center, dog park, Publix, Walgreens, & The Club Health & Rehab Clinic. Easy access to pools, golf courses, dining, shopping & the squares at Spanish Springs & Sumter Landing. Includes gas Golf Cart, Comcast cable TV, high speed WIFI, & Villages Daily Sun.

Fenney Waterview Retreat w/Pool in The Villages
If you are looking for a Tranquil escape, then this is the right home for you. Sit by the pool and overlook the sun dance upon the sparkling water as you sip on your drink or read a great book. This Ultra Clean 3 bed/3 bath home has all of the comforts you'll be looking for. There's plenty of space for you and friends or family as everyone has their own space in the home.
Popular amenities for Lady Lake rentals with a pool
House rentals with a pool

The Villages 4 Golf, PickleBall & a whole lot more

Villages - Priv. Htd. Pool 3BR/2BA, Conv. Location

KingBed w/Cart

The Villages, De La Vista West 1762

The Villages Cozy Cottage. GOLF CART available

Private Pool and Hot Tub in The Villages

Luxury home with a pool and 3 bedroom

Pet Friendly in the Villages!
Condo rentals with a pool

Beautiful 1-Bedroom Standard Villa Near Disney

EarlyTimes on the Withlacoochee!

Beautiful 2-Bedroom Grand Villa Near Disney

Riverside Retreat

Beautiful 1-Bedroom Grand Villa Near Disney

Your Spring Getaway W/ Heated Pool and Bike trails

20 Mi to Disney: Condo w/ Pool Access in Clermont!

River Retreat
Other holiday rentals with a pool

Villa la Bella

Pool Home Great Location 3/2 & 2 Golf Carts

The Villages Spanish Springs Square

King Bed, Small Dogs ok, & Home Water Filter!

Guest Cabina | Hot Tub | Tropical Pool Oasis

Cozy Pool Cottage by Lake Weir

New, private pool getaway in The Villages, FL

Willie’s Place w/ Golf Cart, Hot Tub & Lanai | Dog
When is the best time to visit Lady Lake?
| Month | Jan | Feb | Mar | Apr | May | June | July | Aug | Sept | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $182 AUD | $189 AUD | $199 AUD | $158 AUD | $150 AUD | $137 AUD | $128 AUD | $133 AUD | $137 AUD | $142 AUD | $154 AUD | $167 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 Lady Lake

Total holiday rentals
Explore 80 holiday rentals in Lady Lake

Nightly prices starting at
Lady Lake holiday rentals start at $83 AUD per night before taxes and fees

Verified guest reviews
Over 960 verified reviews to help you choose

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

Pet-friendly accommodation
Find 50 rentals that welcome pets

Rentals with dedicated workspaces
40 properties have a dedicated workspace

Wi-Fi availability
80 of Lady Lake holiday rentals include Wi-Fi access

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

4.9 Average rating
Lady Lake stays are highly rated by guests—averaging 4.9 out of 5!
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- Universal Studios Florida
- Walt Disney World Resort
- Universal Orlando Resort
- Walt Disney World Resort Golf
- Orange County Convention Center
- Disney Springs
- SeaWorld Orlando
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- Magic Kingdom Park
- Orlando / Kissimmee KOA
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- Island H2O Live!
- University of Central Florida
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