Vacation rentals with a pool in Lady Lake

Find and book unique homes with a pool on Airbnb

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 €43 per night before taxes and fees
Verified guest reviews
Over 990 verified reviews to help you choose
Family-friendly vacation rentals
40 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
4.9 Average rating
Lady Lake stays are highly rated by guests—averaging 4.9 out of 5!

Top-rated rentals with a pool in Lady Lake

Guests agree: these homes with a pool are highly rated for location, cleanliness, and more.

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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

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

4.95 out of 5 average rating, 155 reviews

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

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.

4.96 out of 5 average rating, 353 reviews

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

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.

4.98 out of 5 average rating, 162 reviews

Top guest favorite

The exterior of a single-story villa is highlighted, featuring a yellow facade with a two-car driveway and a well-maintained landscape. Lush green shrubs and palm trees are observed, alongside colorful planters that add vibrancy to the entrance.

Home in The Villages

Villa la Bella

Stay in one of the most desirable locations in The Villages in the village of Sable Chase. Our beautifully remodeled and newly updated villa is just minutes from Sumter Landing Town Square in the heart of The Villages. Bright and airy feeling, tastefully designed and decorated, it features hardwood floors throughout. The 2BD, 2BA house with cozy lanai and new stainless gas grill also includes a Yamaha gas golf cart for your use. Your Villages vacation is ready for you at Villa la Bella!

4.94 out of 5 average rating, 101 reviews

Top guest favorite

An elegantly appointed dining area is highlighted by a dark table surrounded by gray upholstered chairs. Two candles sit atop the table, with a decorative bowl in the center. Soft lights hang overhead, illuminating the blue walls adorned with framed art and decorative shelves.

Villa in The Villages

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. Golf cart included in price 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!

4.86 out of 5 average rating, 276 reviews

Top guest favorite

An extended lanai features a dining table surrounded by cushioned chairs, with views of a heated saltwater pool and lush greenery beyond. Comfortable seating arrangements are designed for relaxation, while ceiling fans provide a gentle breeze throughout the open space.

Home in The Villages

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

Enjoy this unique, tranquil getaway in a new 2023 home less than 3 miles from Sawgrass Grove (nightly entertainment, restaurants), and only a few blocks from Mickylee Pitch and Putt, Jubilee Putting Course, and the new Franklin Recreation Center. Ezell, Homestead, and Citrus Grove Rec Centers are all under 3 miles away. Back yard with lanai, pool with fountain, pond, and trees is a RARE find in The Villages! 3 king bedroom suites! Golf cart (4 seats) available for an additional fee.

4.98 out of 5 average rating, 115 reviews

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

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!

5.0 out of 5 average rating, 127 reviews

Superhost

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

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.

4.83 out of 5 average rating, 133 reviews

Top guest favorite

Home in The Villages

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.

4.97 out of 5 average rating, 106 reviews

Top guest favorite

The image captures a welcoming street view of a residential area with charming homes featuring varied architectural styles. Lush palm trees and neatly trimmed shrubs outline the landscaped front yards. The sky is bright with fluffy clouds, contributing to the overall inviting atmosphere.

Home in The Villages

1199 Merryweather - Walk to Lake Sumter Sq 3nt min

Wow! Gorgeous 2br/2ba courtyard villa w/5-star reviews. Walk to Creekside Landing pool & town square in THE most sought after location in the community. Private yard. Granite counters, vaulted ceilings, big birdcage, French doors & vinyl plank floor. No carpet. Nice recliners, patio chairs, and sofa. King in master br. Queen in guest br. Cable. WIFI. Rent a golf cart (optional). No pets here. I manage a pet friendly 3br across street (sleeps 6). Rest of 2026 is just a 3nt min.

4.94 out of 5 average rating, 101 reviews

Top guest favorite

The modern home features a spacious driveway leading to a large carport and a two-car garage. A covered porch with steps provides access to the front entrance, surrounded by greenery and trees.

Home in Lady Lake

Villages home with unique elevated front porch

A bright 2 bed, 2 bath home with new flooring throughout, includes golf cart. Located in historic Country Club Hills. Less than two miles from Spanish Springs Square with restaurants, shops & FREE nightly entertainment. Minutes away from pools, hot tubs, recreation centers, walking paths, & golf courses. Fully equipped kitchen with starter pack. Relax with a book & a drink on the breezy front porch with an overhead fan. Free Netflix, Peacock Premium & high speed internet.

5.0 out of 5 average rating, 66 reviews

Guest favorite

Home in Lady Lake

The Promise Land~10 beds~New

Set on 158 breathtaking acres in Lady Lake, FL, our scenic home features rolling green pastures, majestic oak trees, and stunning sunsets that create the perfect backdrop for unforgettable weddings, elopements, and special events. With wide-open natural landscapes, abundant wildlife, and peaceful surroundings, it’s an ideal setting for ceremonies, receptions, retreats, and celebrations just minutes from The Villages and about an hour from Orlando.

4.97 out of 5 average rating, 77 reviews