Vacation rentals in Lady Lake, FL with a pool

Explore 5 vacation rentals, homes, and villas with pools in Lady Lake, FL for your next getaway or business trip. Step outside to your own private or shared pool and into a home filled with premium amenities such as Air Condition Homes, Homes with Free Parking and Pet-Friendly Homes. Throughout your stay, unwind poolside, soak up the sun, and enjoy an outdoor space designed for relaxation. With options starting as low as $83 per night and homes offering up to 3 bedrooms and 3 bathrooms, it's easy to book a comfortable, personalized stay. You'll also have access to high-speed Wi-Fi and 24/7 local support, creating a more secure, connected atmosphere for your trip. Marriott Bonvoy members enjoy the added benefit of earning points on every stay, so each trip's more rewarding than the last. Book your next poolside escape with Homes & Villas by Marriott.

5 Homes with Pools in Lady Lake

Private Pool & Golf Cart! Villa By Spanish Springs

The Villages, FL, US
2 Bedrooms 6 Guests
Aug 21 - 26
night

Must Be 55+ to Book | Golf Cart Provided | Remote Work Ready This 2-bed, 2-bath vacation rental brings The Villages lifestyle right to your backyard! A private, solar-heated pool lets you swim through every season, the Florida room provides a sunny spot to work, and the courtyard patio is perfect for coffee or cocktails. Hop on the golf cart to discover everything from live music to local dining at Spanish Springs, then come home to a villa that feels like your own private retreat! -- THE PROPERTY -- SLEEPING ARRANGEMENTS - Bedroom 1: 1 queen bed - Bedroom 2: 1 queen Murphy bed - Living Room: 1 queen sleeper sofa THE VILLAGES AMENITIES (w/ $50 fee for 2 passes, paid on-site) - 100+ pools: family pools, indoor pools, sports pools & neighborhood pools - 107 unique recreation centers - 240+ pickleball courts, 201 bocce ball courts - 5 racquetball courts, 25 tennis courts - 174 shuffleboard courts - 930 acres of nature preserves w/ walking trails - Town squares w/ nightly live entertainment - 46 executive golf courses & 10 championship courses (prior reservations required) OUTDOOR OASIS - Private saltwater pool (solar-heated only) - Furnished patio, gas grill - Lounge chairs, umbrella - Landscaped garden HOME HIGHLIGHTS - 2 Smart TVs - Large dining table - Florida room, desk w/ printer - Washer & dryer KITCHEN - Refrigerator, stove/oven, dishwasher - Drip/Keurig coffee maker - Toaster, microwave - Cooking basics, dishware & flatware GENERAL - Free WiFi - Central A/C & heating - Laundry detergent, iron & board - Linens & towels, shampoo, hair dryer FAQ - Golf cart & private pool (waiver required) - 55+ community ACCESSIBILITY - Single-story home, step-free access PARKING - Driveway (1 vehicle) - Free street parking (first-come, first-served)  -- THE LOCATION -- - Across the street from Tierra Del Sol Country Club: golfing, adults-only pool - 2 miles to Spanish Springs Town Square & Sharon L. Morse Performing Arts Center: dining, shops & events - 3 miles to Lake Sumter Landing: waterfront dining & boutique shopping - 9 miles to Brownwood Paddock Square & Barnstorm Theater - 13 miles to Sawgrass Grove & 15 miles to Eastport - 71 miles to Orlando Int'l Airport -- REST EASY WITH US -- Evolve makes it easy to find and book properties you’ll never want to leave. You can relax knowing that our properties will always be ready for you and that we’ll answer the phone 24/7. Even better, if anything is off about your stay, we’ll make it right. You can count on our homes and our people to make you feel welcome — because we know what vacation means to you. -- POLICIES -- - No smoking - No pets allowed - No events, parties, or large gatherings - Must be at least 55 years old to book - Additional fees and taxes may apply - Photo ID will be required upon check-in ADDITIONAL INFORMATION - This single-story home offers step-free access - A waiver is required prior to using the golf cart and private pool - The pool is heated solely by rooftop solar panels, and the water temperature may vary and cannot be adjusted - This property is located in a 55+ active-adult community. The guest booking the property must be at least 55 years old - Guests may reach out to the Guest Contact to arrange the purchase of an amenities pass for $50. This fee includes 2 passes and a gate pass; extra passes may be purchased for an additional fee Licence number: DWE7000758

Allenwood Pool Home at The Villages

The Villages, Florida, US
3 Bedrooms 6 Guests
Aug 20 - 25
$174 night

Allenwood Pool House | Private Heated Pool • Outdoor Kitchen • Golf Cart • Near Lake Sumter Landing Escape to Allenwood Pool House, a beautifully appointed designer home in the desirable Village of Amelia, where resort-style outdoor living meets one of the most convenient central locations in The Villages. Featuring a private pool, outdoor kitchen, dedicated workspace, and complimentary golf cart, this home is perfect for golf vacations, extended stays, snowbirds, or simply enjoying everything The Villages has to offer. The Home This beautifully designed 3-bedroom, 2-bath home comfortably accommodates up to six guests with an open floor plan that creates the perfect gathering space for family and friends. Sleeping Arrangements Primary Suite: King bed, Smart TV, private ensuite bathroom with walk-in shower Guest Bedroom 1: Queen bed with Smart TV Guest Bedroom 2: King bed with Smart TV Guest bathroom with full bathtub Every bedroom includes its own television, and the spacious living room also features a large Smart TV for relaxing after a day exploring The Villages. Chef’s Kitchen Whether you’re preparing breakfast before golf or hosting dinner with friends, the kitchen is fully equipped with everything you’ll need. Features include: Granite countertops Large center island Gas stove Upgraded stainless steel appliances Fully stocked cookware, dishes, utensils, and small appliances Coffee maker Pantry storage Dining options include: Dining table seating for 6 Breakfast nook seating for 4 Kitchen island with bar seating Outdoor Living The backyard is designed to make every day feel like a vacation. Enjoy: Private swimming pool Optional pool heat (additional fee) Outdoor kitchen Covered lanai Comfortable outdoor seating Private patio terrace Whether you’re enjoying your morning coffee, grilling dinner, or relaxing by the pool after a round of golf, this outdoor space is one of the home’s highlights. Dedicated Workspace Need a quiet place to work? The den features: Desk Comfortable office chair Quiet space for remote work, reading, or conference calls Included Amenities Complimentary high-speed Wi-Fi Smart TVs in the living room and every bedroom Full-size washer and dryer Fully equipped kitchen Linens and towels provided Two-car garage Complimentary 2-passenger gas golf cart Explore The Villages The Village of Amelia is one of the most sought-after central neighborhoods in The Villages, offering easy golf cart access to shopping, recreation, golf, and entertainment. Lake Sumter Landing Approximately 4 miles | About 10–15 minutes by golf cart Lake Sumter Landing is one of The Villages’ three iconic town squares and features: Free nightly live entertainment Waterfront restaurants Boutique shopping Happy hours Coffee shops Ice cream Seasonal events Movie theater Brownwood Paddock Square Approximately 8 miles | About 20–25 minutes by golf cart or 15 minutes by car Brownwood offers: Free nightly live music Restaurants Shopping Farmers markets Seasonal festivals Dancing Entertainment throughout the year Recreation Nearby With Temporary Resident IDs, guests may enjoy access to The Villages’ outstanding recreation system, including neighborhood and regional recreation centers, pools, pickleball, tennis, bocce, shuffleboard, clubs, and organized activities. Amelia Neighborhood Recreation Center Approximately 2 minutes away Features include: Adult pool Shuffleboard Bocce Horseshoes Social activities Pavilion Colony Cottage Regional Recreation Center Approximately 10 minutes away Offers: Sports pool Pickleball Tennis Billiards Meeting rooms Daily activities Fitness classes Lake Miona Regional Recreation Center Approximately 10 minutes away Features: Sports pool Pickleball Tennis Fitness activities Arts & crafts Clubs Indoor recreation Golf Golf enthusiasts will love the location. Numerous Executive Golf Courses and Championship Golf Courses are just minutes away by golf cart, giving you endless opportunities to play throughout your stay. Shopping & Dining Within just a few minutes you’ll find: Publix Fresh Market Walmart Target Walgreens CVS Pharmacy Banking Medical facilities Countless restaurants Golf cart-accessible shopping and dining Temporary Resident IDs Guests staying with AJ Home Rentals may purchase Temporary Resident IDs (approximately $50 per household, payable directly to The Villages when picking up the IDs). Temporary Resident IDs allow eligible guests to enjoy many of the community’s outstanding amenities, including recreation centers, pools, executive golf (trail fees may apply), organized activities, and more. Please note that Temporary Resident IDs are not Guest Passes and are issued by The Villages based on eligibility and availability. Golf Cart A complimentary 2-passenger gas golf cart is provided for your convenience. Guests who wish to use the golf cart must complete AJ Home Rentals’ Golf Cart Waiver before arrival. The golf cart is provided as a complimentary amenity. While we make every effort to ensure it is available, unforeseen maintenance, repairs, recalls, weather, or other circumstances may occasionally prevent its use. No refunds or credits will be issued for golf cart interruptions. Pet Policy We welcome well-behaved dogs upon prior approval. Dogs require advance approval. Breed, age, weight, and house-training information may be requested. Additional pet fees may apply. Cats are not permitted. Whether you’re planning a golf getaway, an extended seasonal stay, or a relaxing Florida vacation, Allenwood Pool House offers the perfect blend of comfort, convenience, and resort-style living in the heart of The Villages. From the private pool and outdoor kitchen to the golf cart and unbeatable location near Lake Sumter Landing and Brownwood, everything is here for an unforgettable stay.

Keystone Haven Villa (Hadley)

The Villages, FL, US
2 Bedrooms 4 Guests
Sep 1 - 6
$107 night

PET FRIENDLY WITH PET DOOR AND FENCED YARD 🏝️ Welcome to Coastal Haven Villa: Your Tropical Retreat in The Villages of Hadley! Nestled in the picturesque VILLAGES OF HADLEY, Coastal Haven Villa is a delightful 2-bedroom, 2-bathroom home perfect for those seeking a tropical escape. Decorated with ocean-inspired decor, this villa offers a unique blend of coastal charm and modern comfort. With its private patio and spacious lanai, this home is an ideal retreat for relaxation and enjoyment. ✨ Impeccable Comfort & Tropical Vibes Step into a bright and inviting space designed to make you feel right at home. The villa features a SPACIOUS KITCHEN equipped with all the essentials for preparing delicious meals, including modern appliances and ample counter space. The cozy dining area is perfect for enjoying meals together, while the open living area boasts a BIG TV MOUNTED ON THE WALL, providing a great space for entertainment and relaxation. Both bedrooms are thoughtfully designed for comfort, with the master suite offering a private bathroom. The second bedroom is perfect for guests or additional family members. The home includes a STORM DOOR to let in plenty of natural light, enhancing the bright and airy atmosphere. 🏖️ Outdoor Bliss & Entertainment One of the standout features of Coastal Haven Villa is the TIKI BAR in the back, perfect for enjoying tropical drinks and the laid-back Florida lifestyle. The villa also boasts a NICE SIZE OUTDOOR LANAI AND PATIO, ideal for dining al fresco or simply relaxing in the sun. The PRIVATE PATIO offers a peaceful retreat, surrounded by lush greenery. For those who love to grill, a BBQ is available, making it easy to host outdoor gatherings. The home also includes a 1-CAR GARAGE AND GOLF CART GARAGE, providing ample space for your vehicle and the GOLF CART provided for your convenience. 🌴 Explore The Villages & Beyond Conveniently located close to LAKE SUMTER LANDING, Coastal Haven Villa offers easy access to a wealth of amenities and activities. Enjoy the vibrant atmosphere of Lake Sumter Landing, with its variety of shops, restaurants, and nightly entertainment. The HADLEY POOL is just a short distance away, perfect for a refreshing swim. For golf enthusiasts, the villa is ideally situated near major executive and championship golf courses, providing endless opportunities to enjoy the sport. Residents with a VILLAGES TEMPORARY RESIDENT ID (available for a $50 fee paid directly to The Villages) can enjoy access to 40+ EXECUTIVE GOLF COURSES throughout the community. These courses offer a range of challenges for all skill levels and are included in the amenities accessible during your stay. This ID also provides access to numerous recreational facilities, making it easy to enjoy the active lifestyle that The Villages is known for. 🌟 Your Coastal Paradise Awaits Don’t miss the opportunity to experience the best of The Villages at Coastal Haven Villa. Whether you’re looking to relax in a tropical setting or explore the vibrant community, this villa is the perfect home base for your adventures. This is a non-smoking property. The Villages is an active senior community for residents 55 YEARS AND OLDER.

Glendale Poolside Retreat

The Villages, FL, US
3 Bedrooms 6 Guests
Aug 20 - 25
$219 night

IMPORTANT !!! JAN-MAR only full month bookings / no partial bookings allowed Other times of the year - Minimum two-week stays. 🌟 Glendale Poolside Retreat in the Village of Charlotte 🌟 Discover the perfect blend of luxury and relaxation at Glendale Poolside Retreat, an elegant 3-bedroom, 2-bathroom designer home in the desirable Village of Charlotte. Just a short stroll to the Captiva Family Pool and Recreation Center, this beautifully furnished residence offers a private pool and is ideally located close to Brownwood Paddock Square and just a quick ride to Lake Sumter Landing. 🏡 Sophisticated Living & Stunning Design Step inside and experience the grandeur of this beautifully designed home. The open floor plan seamlessly connects the living, dining, and kitchen areas, providing an inviting space for relaxation or entertaining. The home features tile floors, soaring ceilings, and sophisticated finishes that create an atmosphere of timeless charm. The master suite includes a luxurious king bed and a private bathroom, while the guest rooms offer a queen bed in one and two twin beds in the other. Each bedroom is designed for comfort and style, ensuring a restful stay. 🌞 Private Poolside Oasis Step outside through the glassed-in lanai to find your private poolside escape enclosed within a spacious birdcage. Whether you’re lounging poolside or hosting a BBQ, this tropical oasis is perfect for making the most of the Florida sunshine. With lush surroundings and ample seating, your outdoor space invites relaxation and fun in equal measure. Solar system for temperature controls - no heat pump 🌴 Explore The Villages! As a guest at Glendale Poolside Retreat, you’ll enjoy all the incredible amenities of The Villages, Florida’s premier 55+ active adult community. For a small fee, obtain a Villages Temporary Resident ID and access over 40 executive golf courses, resort-style pools, and recreation centers that offer everything from tennis and pickleball to fitness classes. Choose from family pools, lap pools, and adult-only pools to suit your mood. 🚶‍♀️ Prime Location: Convenience at Your Doorstep Located just minutes from Brownwood Paddock Square, where you can enjoy live music, dining, and shopping, and a quick ride to Lake Sumter Landing, this home offers the perfect balance of peaceful living and access to entertainment. With Captiva Recreation Center just around the corner and other centers close by, you’ll always have something fun to do. This stunning home in the Village of Charlotte offers a private pool, luxurious accommodations, and easy access to all the excitement of The Villages. Experience the best of both worlds with convenience, comfort, and relaxation at your fingertips. Solar system for temperature controls - no heat pump

Private Pool & Lake Views: Family Home in Oxford

The Villages, FL, US
3 Bedrooms 10 Guests
Aug 20 - 25
$333 night

Spend your next Florida family getaway with a stay at this beautiful 2-story house with a lake view and a large swimming pool! This 3-bedroom, 3-bath Oxford vacation rental features a private backyard, furnished screened porch, and just a short walk from Lake Miona which includes a playground, beach, and boat ramp! Explore shops and restaurants around nearby Lake Sumter Landing, check out kayaking at Lake Griffin State Park, or plan a day trip to Disney or Universal Studios while in town! -- THE PROPERTY -- Fireplace | Screened Porch | 2 Mi to Lake Sumter Landing | Water Views Bedroom 1: California King Bed | Bedroom 2: 2 Twin Beds | Bedroom 3: 2 Twin Beds | Living Room: 2 King Air Mattresses INDOOR LIVING: Smart TVs, board games, books, dining table, walk-in closet, en-suite bathroom, walk-in showers, garden tubs, ceiling fans OUTDOOR LIVING: Private pool, spacious deck, patio seating, outdoor dining, rocking chairs, basketball goal, fire pit KITCHEN: Refrigerator, drip coffee maker, stove/oven, microwave, dishwasher, toaster oven, kitchen island, dishware & flatware, cooking basics GENERAL: Self check-in, free WiFi, central heating & A/C, washer & dryer, laundry detergent, iron/board, towels/linens, trash bags/paper towels, complimentary toiletries, hair dryer FAQ: Pet fee (paid pre-trip) ACCESSIBILITY: 2-story house, 2 steps required to enter, interior stairs required to reach all bedrooms on 2nd floor PARKING: Carport (3 vehicles), driveway (8 vehicles), RV parking allowed (electrical hookups on-site) -- THE LOCATION -- NEARBY ATTRACTIONS: Lake Sumter Landing (2 miles), Spanish Springs Town Square (6 miles), Brownwood Paddock Square (7 miles), Venetian Gardens (14 miles) OUTDOOR FUN: Lake Miona Park & Boat Ramp (0.3 miles), Lake Miona Park (0.3 miles), Lake Griffin State Park (10 miles), Eaton's Beach at Lake Weir (12 miles) HIT THE LINKS: Lopez Legacy Golf & Country Club (6 miles), Hacienda Hills Golf & Country Club (6 miles) FLORIDA DAY TRIPS: Universal Studios (57 miles), Disney World (58 miles), Downtown Orlando (58 miles) AIRPORTS: Leesburg International Airport (18 miles), Orlando International Airport (65 miles) -- REST EASY WITH US -- Evolve makes it easy to find and book properties you'll never want to leave. You can relax knowing that our properties will always be ready for you and that we'll answer the phone 24/7. Even better, if anything is off about your stay, we'll make it right. You can count on our homes and our people to make you feel welcome — because we know what vacation means to you. -- POLICIES -- - No smoking - Pet friendly w/ $150 fee (+ fees & taxes) - No events, parties, or large gatherings - Must be at least 25 years old to book - Additional fees and taxes may apply - Photo ID may be required upon check-in - NOTE: While this 2-story house only requires 2 steps to enter, an interior staircase is required to reach all of the home’s bedrooms on the 2nd floor - NOTE: This property sleeps 6 guests in 5 beds, with room for 10 total by using the air mattresses

Vacation Rentals in Lady Lake by Amenities & Features

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Vacation Rentals Near Lady Lake

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