
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.

Perfect location Lake Sumpter Villa w/ Golf Cart
Newly opened availability! January and February open for monthly stays. Please message me to inquire . Jan.1 - Jan.31 Feb.1 - Feb.28 5% discount if you book both months. Location, Location, beautiful 2 bedroom villa with 2-seater golf cart, is located in the desirable neighborhood of Creekside Landing. This villa is within walking distance of Lake Sumter Landing town square where you will find shopping, restaurants, a movie theater and FREE nightly live entertainment. Edgewater neighborhood Recreation Center with a pool, as well as Canal Street Recreation Center with activities such as shuffleboard courts, bocce courts, card rooms and so much more. This villa is beautifully decorated in a warm and inviting style. The kitchen is fully equipped with everything you’ll need to prepare meals and entertain friends. The living room offers plenty of comfortable seating with a flat screen TV. The master bedroom has a king size bed, flat screen TV, large walk-in closet and a private master bath with a walk-in shower, complete with towels and linens. The guest bedroom and guest bath comes completed with lines and towels for your guest’s comfort. There is a screened lanai with comfortable seating and a privacy wall . This villa comes complete with WiFi. With the purchase of resident ID cards you can use any of the 29 executive golf courses with no greens fees. You pay resident rates in greens fees at the 11 championship courses. You are also entitled to use any of the family- friendly and adult (30 and older) swimming pools, and organized activity swimming pools, There are over 1,000 organized activities each week through the recreation centers. Rates are based on double occupancy. Rates shown do not include taxes and additional fees

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

The 19th Hole - Walk to Spanish Springs Square
Recently remodeled home. This Courtyard Villa is just 0.3 miles to the center of Spanish Springs Square. You’ll recognize Spanish Springs Town Square by its unique fabled history from the exteriors of the shops to the fountains on the square. Walk to nightly entertainment. This 2 bedroom, 1 bathroom with King Size bed in the Master Bedroom. Queen bed in the guest bedroom. Sofa bed in the living room. Enclosed rear yard. 75-inch TV. Complete with linens, washer/dryer, kitchen equipment and WiFi.

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.

•Hot Tub & Golf Cart - Courtyard Villa•
Our newest 5 Star ⭐ listing with a heated swim spa (additional fee) & golf cart in the heart of Spanish Springs minutes from everything you’ll need. Enjoy the town squares, live music, bars, golf and much more 🎶 The home has a dipping pool/spa that has swim jets that allows you to swim against for exercise. Enjoy the outside courtyard with a BBQ and patio furniture Home in the heart of The Villages, a 7 min golf cart ride from Spanish Springs, 15 min from Sumter Landing, Brownsville-30min

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 .

Del Mar Paradise, The Villages, Golf Cart, Bikes!
Del Mar Paradise in The Villages! Beautifully furnished home with Golf Cart & Bikes! Bring your family & grandchildren; sleeps 6. 2 large bedrooms, Florida Room with twin, & 2 full baths. Fully equipped kitchen, tiled rooms, BBQ. Large front yard! Short walk/drive to Spanish Springs Town Square to enjoy a great meal, see a show, shop, dance to live music nightly! Close to Chula Vista Recreation Center & Golf Course, pool & courts! 2 dogs under 30 lbs each. Dog fees cleaning see Details

The Villages 4 Golf, PickleBall & a whole lot more
Our home has everything you need for comfort & ease when you are not out enjoying "The Villages Lifestyle". It is on the "Historic Side". Walk to Spanish Springs Town Square, Publix, restaurants & shopping. Paradise Park is a short walk away where you can enjoy the shaded pathways. Hang out at the archery field or take in some self guided exercise with outdoor equipment. So much to enjoy so little time to take it all in! Note: The Villages is an active adult community. No work crews.

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!

Tranquil guest home with beautiful salt water pool
Our tranquil getaway! Whether on vacation or traveling for work, this is the place to stay! With a beautiful pool and gigantic screened in area with comfortable patio furniture and a place to have your meals outside, you can't beat our guest house for enjoying Florida's weather. Inside, we have just added a stunningly comfortable new Queen sized bed with a "Purple" mattress on an adjustable frame. We have hi speed wi-fi and a large screen TV with Amazon Prime, Netflix, and more.

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.
Popular amenities for Lady Lake rentals with a pool
House rentals with a pool

Beautifully Furnished 3/2 with In-ground Pool

Calming Pool Oasis in Fenney, The Villiages FL

The Villages, De La Vista West 1762

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

Heart of The Villages-guest pass for pool, golf

Cozy Pool Cottage by Lake Weir

Pet Friendly in the Villages!

Screened-In-Optional Heated Pool+Fence+Arcade +Bbq
Other vacation rentals with a pool

Villa la Bella

Oasis in Heart of The Villages

Pool Home Great Location 3/2 & 2 Golf Carts

The Villages Spanish Springs Square

Lovely Home in the Villages with a golf cart

Camp St. Cabanas Unit 3- POOL & HOT TUB

Pirates & Parrots - The Villages - w/Golf Car !

Magazine Featured Ranch Home on 11 Serene Acres
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.ﺇ375 | ﺩ.ﺇ408 | ﺩ.ﺇ441 |
| 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 90 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 1,050 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
90 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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