Holiday rentals with a pool in Ocala

Cozy Fall Escape: Family & Pup Fun w/ Pool & Yard

Relax & play at Henry’s Hideaway, an inviting 1.5-acre retreat built for family fun & laid-back living. Relaxation & Fun: Above-ground pool Screened lanai w/ 65" smart TV Games & entertainment options Outdoor Living: Dining table for 8 on the lanai Gazebo w/Weber grill, party lights & fire pit Game Room: Billiards, arcade games, mini fridge Detached but close to main house Entertainment & Connectivity: Smart TVs in living room, lanai, king rooms & game room Strong WiFi indoors & out

Beautiful Home with Pool Near HITS (Horse Country)

Relax with the whole family in this 3 bedroom, 2 bath updated home near HITS (Ocala’s Beautiful Horse Farms), Disney, Beaches & Springs. Home is 1 block from Publix Grocery Store & Restaurants. Located about an hour from Ormond/Daytona Beach, Disney World & Orlando area. If you like Florida’s nature areas, the home is about half an hour to Juniper Springs, Salt Springs & minutes to Silver Springs. Bring your kayaks/canoes. Gulf fishing and several lakes nearby. Just minutes from Downtown Ocala!

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.

GameRoom*Pool+LanaiHangOut*OpenConcept*

Step into a coastal-inspired retreat where the charm of an ocean resort meets the comfort of home. This spacious 4-bedroom, 2-bath getaway offers everything you need for a memorable family vacation—from a uniquely designed swimming pool to a lively game room and a serene lanai perfect for unwinding. Inside, the open-concept layout seamlessly connects the living room, dining area, and kitchen, creating a warm and welcoming space ideal for gathering, entertaining, and making lasting memories.

Modern Guest Suite w/pool, near Paddock Mall & WEC

Beautiful 3 room apartment in upscale, gated community close to Paddock Mall w/ easy access to restaurants, WEC, HITS, Springs, State Parks, etc. Owners live onsite opposite pool across from the suite. Our peaceful neighborhood has oaks, owls etc. Suite is clean & comfortable with private access & opens to pool & walled courtyard patio area. Kitchenette provides simple cooking with skillet, etc. but no range. Master bed has queen bed with own TV and there's a large TV in living area.

Farm by Santos trails & the Villages

Come experience a restful stay in our farm! We have a mother in law suite that is completely private with the most comfortable bed you will ever sleep on. We have 8 laying hens and 3 cows. They love to be fed and sang to. You will be surrounded by beautiful oak trees and nature. 15 minutes away you have the very popular Villages as well as the famous Santos trails with trails for biking, walking, and horse back riding! Bring your RV, trailers, and animals as we have room for all.

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

Near WEC & HITS - Huge Backyard

Welcome to your perfect escape near the World Equestrian Center (WEC) and HITS! Our fully renovated home offers a blend of modern luxury and comfort, ensuring a delightful stay for you and your guests. - Prime Location - Spacious Interiors - Huge Backyard - Comfort & Convenience - High-speed Wi-Fi Book now and experience the best of both worlds – tranquility and excitement – in our luxurious retreat!

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.