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.

%{current} / %{total}1 / 1
Top guest favorite
The exterior of the villa is showcased, featuring a well-maintained facade with a garage and a driveway. Lush palm trees and neatly trimmed bushes contribute to the inviting landscape, while a white privacy wall offers additional seclusion. The dynamic sky adds a vibrant backdrop.
Villa in The Villages
4.99 out of 5 average rating, 71 reviews

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

Top guest favorite
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 favorite
A classic arcade game console stands in the living area, featuring the popular game 'Golden Tee'. The console is situated next to wooden furniture, which includes a desk with a chair. A large TV is visible in the background, along with decorative elements on the wall.
Villa in Lady Lake
4.86 out of 5 average rating, 50 reviews

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.

Top guest favorite
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.

Guest favorite
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 favorite
An exterior view of a home features a golf cart parked in the driveway, along with a glimpse of the garage entrance. The porch includes a potted plant, and the front windows display shutters. Circular insets showcase the dipping pool, pool table, and foosball table.
Home in Lady Lake
4.88 out of 5 average rating, 17 reviews

•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

Guest favorite
The private pool area is enclosed by a screened lanai, illuminated by string lights. A relaxing area features loungers beside the pool, with a raised spa and gentle water feature. Lush greenery surrounds the space, creating a serene atmosphere.
Villa in Lady Lake
5 out of 5 average rating, 24 reviews

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 .

Top guest favorite
A one-story home with a spacious landscaped front yard is depicted. An inviting golf cart is parked on the curved driveway, which leads to the entrance, flanked by ornamental shrubs and shaded by a large tree. The sky is clear, enhancing the outdoor appeal.
Home in Lady Lake
4.97 out of 5 average rating, 34 reviews

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

Superhost
A inviting living room features a comfortable seating arrangement with a green armchair and a blue accent chair. A colorful area rug lies on the hardwood floor, while natural light enters through large windows. A TV is positioned on a low wooden unit, with a decorative table beside it.
Home in Lady Lake
4.89 out of 5 average rating, 38 reviews

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.

Top guest favorite
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 favorite
Guesthouse in Inverness
4.9 out of 5 average rating, 147 reviews

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.

Guest favorite
An exterior view of the patio villa showcasing a well-maintained façade. A garage door is located to the left, with a Yamaha gas golf cart parked on the driveway. A white picket fence and colorful flowers enhance the entrance.
Villa in The Villages
4.85 out of 5 average rating, 117 reviews

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

When is the best time to visit Lady Lake?

MonthJanFebMarAprMayJunJulAugSepOctNovDec
Avg. priceﺩ.ﺇ510ﺩ.ﺇ577ﺩ.ﺇ525ﺩ.ﺇ419ﺩ.ﺇ397ﺩ.ﺇ364ﺩ.ﺇ338ﺩ.ﺇ353ﺩ.ﺇ364ﺩ.ﺇ375ﺩ.ﺇ408ﺩ.ﺇ441
Avg. temp16°C18°C20°C22°C25°C27°C28°C28°C27°C24°C20°C17°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!

  1. Airbnb
  2. United States
  3. Florida
  4. Lake County
  5. Lady Lake
  6. Rentals with pools