Holiday rentals with a pool in Ocala

An outdoor living area features a screened enclosure overlooking a golf course. The pool is surrounded by a spacious patio with a dining set, lounge chairs, and a seating area. Sunlight filters through tall trees, creating a serene atmosphere.

4.97 out of 5 average rating, 31 reviews

Stunning Private Oasis with Pool near WEC

Relax and unwind in this stunning fully renovated modern home with an incredible golf course view from the outdoor living area. Grill poolside or cook in with the gourmet kitchen, lounge by the fire pit poolside or cozy up on the large sofa by the fireplace. Located on Ocala National Golf Course 8 min. to World Equestrian Center 20 min. to Historic Downtown Ocala Square 40 min. to Univ of FL (Gainesville) 45 min to Gainesville Airport Exterior security cameras: pool, driveway, front door

An outdoor seating area features two woven sofas positioned around a central coffee table, offering a comfortable spot to relax. A ceiling fan hangs above, and a door leads to the interior. A screened enclosure allows for views of the pool and surrounding greenery.

4.94 out of 5 average rating, 146 reviews

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!

4.96 out of 5 average rating, 344 reviews

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.

A dining area showcases a wooden table surrounded by six intricately designed chairs. Natural light filters through large windows, offering a view of the screened-in pool. The kitchen features modern blue cabinetry and sleek countertops, creating a cohesive and inviting space.

4.96 out of 5 average rating, 112 reviews

Screened-In-Optional Heated Pool+Fence+Arcade +Bbq

Minutes away from I-75, ready for you and your family to venture off & explore any part of Florida. Garage turned into a game room & Enjoy the Pool Longer – Solar & Electric Heated for Extended Spring & Fall Comfort! Our solar-heated-screened in pool lets you enjoy swimming well into the early spring & late fall . For those extra chilly days, also for 50 dollars a day you can enjoy an electric pool heater to ensure the water stays comfortable. Swim season doesn’t have to end when summer does!

4.97 out of 5 average rating, 31 reviews

Magazine Featured Ranch Home on 11 Serene Acres

Experience Chozen Acres, a magazine-featured modern A-frame on 11 serene acres. This 2-bedroom + loft retreat offers ultimate relaxation with a stunning pond, waterfall, gazebo, and charming bridge. Wander among majestic oaks, enjoy the rustic barn, or lounge by the pool. It’s a stylish, zen-filled escape designed for peace. There are 5 doors into the home, the front door will be permanently locked until a custom door has been installed. Book 3+ nights and get a FREE movie of your choice!

The spacious living area features a large sectional sofa adorned with neutral pillows, positioned on a marbled area rug. A modern coffee table is centered in front of the sofa, while a decorative plant adds a touch of nature to the room. Natural light flows in through the front entryway.

4.92 out of 5 average rating, 25 reviews

WEC, HITS, Golf, Pets, Pool- Luxury Designer Villa

This elegant, designer decorated and newly renovated home, is the ideal rental retreat for equestrian enthusiasts, golfers and those looking for central location and yet quiet space to relax. Nestled in a park-like-setting on a quiet cul-de-sac it features a screened in patio and pristine swimming pool. This home overlooks the 15th hole of the Ocala National Golf Course & within less than 5 minutes of Golden Ocala Country Club, WEC-The World Equestrian Center & easy access to OBS & HITS!

An aerial view of a spacious mid-century home is presented, featuring a smooth roofline and an inviting pool area surrounded by lush green landscaping. The well-maintained yard includes palm trees and is accessible from a winding path leading to the entrance.

4.85 out of 5 average rating, 105 reviews

Spacious Home with Pool Near HITS (Horse Country)

Newly updated mid-century home designed with all the top amenities. Truly one of a kind with amazing architectural design. Every detail has been preserved for your entertainment. Great home for family time and entertaining friends. There are 3 spacious bedrooms, a full bar area, patio with games, and pool for your enjoyment. The home is located minutes to Silver Springs and Downtown Ocala. It is located about an hour from Daytona Beach, Disney World & Orlando area. Also near HITS & WEC.

Place to stay in The Villages

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.

5 out of 5 average rating, 124 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!

4.8 out of 5 average rating, 121 reviews

Modern 5 Bedroom Family Home w/Pool and Game Room!

We invite you to relax and unwind in our 5 Bedroom 3 bathroom, spacious pool home located in a quiet cul de sac. Complete with an upstairs game room with air hockey table. Rest and recuperate in the master suite with a custom made king size bed and an oversized jacuzzi tub. There is a large area for parking, will easily fit 4 cars. Easy no contact check in and check out. Whether your in town for fun or business our home has everything you will need to make your trip enjoyable.

A large outdoor pool is surrounded by lush greenery and tall trees, providing a serene environment for relaxation. Clear blue water reflects the sky, and steps lead into the shallow end. A poolside chair is positioned nearby for convenient seating.

4.91 out of 5 average rating, 105 reviews

Ocala Oasis 4BR w/Pool/Cabana/Game Room/Mini Golf

Welcome to our stunning Airbnb located in the beautiful city of Ocala. This exceptional property offers a range of amenities that will make your stay truly unforgettable. With a cabana, a huge pool, a game room, a fire pit, and even a miniature golf course, this is the perfect place to relax and have fun. The ps4 has 7 games you can bring your own as well, ensuring endless entertainment for everyone. The spacious 4-bedroom, 2-bathroom layout provides ample space!

4.92 out of 5 average rating, 141 reviews

Cottage in Clermont

Private Country House | 16 Guests | Gatherings

Bring the whole family to this private 5-acre retreat, situated in one of the few hilly regions of Florida. Enjoy privacy, nature, spectacular sunsets, and starry nights—perfect for relaxing or enjoying outdoor activities. ⚠️ Gatherings require prior approval—please contact us before booking. Note: There is another house on the property that may be rented by other guests. Both are completely private, with no shared areas or parking.

4.92 out of 5 average rating, 153 reviews

A screened lanai features comfortable seating and is positioned adjacent to a well-maintained backyard. A tree is situated in the grassy area, providing shade, while a concrete pathway leads to the entrance. A white fence encloses the yard, enhancing privacy.

Home in The Villages

Briar Meadow Villa - Dogs are welcome!

Dogs are welcome in this nicely furnished Courtyard Villa, with a fenced in backyard. Near Nancy Lopez Legacy Golf & Country Club, Mulberry Grove Rec Center, dog park, Publix, Walgreens, & The Club Health & Rehab Clinic. Easy access to pools, golf courses, dining, shopping & the squares at Spanish Springs & Sumter Landing. Includes gas Golf Cart*, Comcast cable TV, high speed WIFI, & Villages Daily Sun. *Subject to availability

Popular amenities for Ocala rentals with a pool

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

House rentals with a pool

4.97 out of 5 average rating, 143 reviews

An open-concept living area features natural light streaming through large windows with scenic views of the lake. Cozy seating arrangements include a comfortable sectional and accent chairs, complemented by a dining space and a well-equipped kitchen with modern appliances.

Home in Tavares

Lake Dora Dream-Waterfront/Pool

4.67 out of 5 average rating, 64 reviews

3BR w/HUGE pool, patio near WEC/FAST

A tranquil outdoor space features a private heated pool and an attached hot tub, surrounded by a screened enclosure. Lush green landscaping and open skies create a serene atmosphere, while lounging chairs are positioned nearby for relaxation.

4.89 out of 5 average rating, 61 reviews

*No Service Fees* Ocala Equestrian Oasis w/Pool

A charming single-story home is set on a lush green lawn, surrounded by trees and landscaping. A welcoming front porch features a swing and a bright blue door, adding a touch of color to the natural surroundings.

4.93 out of 5 average rating, 123 reviews

Ocala Oasis-3 Bedrooms and Heated Pool!

An aerial view captures a spacious property featuring a fully fenced yard with an above-ground pool, shaded by palm trees. The main house is positioned centrally, accompanied by a driveway leading to two storage buildings. Lush green grass complements the inviting outdoor space.

4.97 out of 5 average rating, 130 reviews

Dog-friendly hideaway w/ pool & game room

A cozy living room is presented with a comfortable sectional sofa and armchairs. A modern coffee table sits in the center, accompanied by decorative lanterns. A large television is mounted on the wall, and natural light enters through the nearby window.

4.85 out of 5 average rating, 120 reviews

Pool Oasis/Game Room/Lanai Hangout/Sleeps 8

4.97 out of 5 average rating, 103 reviews

The exterior of the villa is seen, featuring well-maintained landscaping with palm trees and neatly trimmed shrubs. A spacious driveway leads to the entrance, while a two-car garage is visible on the left. The sunlit facade showcases a welcoming atmosphere.

Home in The Villages

Fabulous Courtyard Villa close to Sumter Landing

A dining area features a glass-top table surrounded by four rattan chairs with white cushions. Behind the table, a light grey cabinet holds decorative items and kitchen appliances. A modern light fixture illuminates the space, enhancing the welcoming atmosphere of the area.

5 out of 5 average rating, 19 reviews

Near WEC & HITS - Huge Backyard

Condo rentals with a pool

4.88 out of 5 average rating, 111 reviews

A spacious pool area is surrounded by lush palm trees and lounge chairs. A shaded gazebo provides seating nearby, while the clear blue water of the pool reflects the sunny sky. Access steps and a gentle slope lead into the inviting pool.

Condo in Gainesville

Cozy Retreat 2BR Escape Near Celebration Pointe

4.75 out of 5 average rating, 12 reviews

Condo in Welaka

Riverfront, Fishing and Boating Paradise, Pool!

Condo in Haile Plantation

4.95 out of 5 average rating, 144 reviews

Haile Village 2 bed/2 bath w Pool & Gym Access

4.83 out of 5 average rating, 205 reviews

A wooden dock extends over calm waters, where a boat is moored alongside. Lush greenery and palm trees border the area, complemented by buildings in the background. The clear blue sky enhances the serene atmosphere of the waterfront setting.

Condo in Crystal River

Crystal River Bungalow with boat slip

5 out of 5 average rating, 8 reviews

Condo in Gainesville

Nestled Oaks - Bright 2BR, 2BA Condo

5 out of 5 average rating, 17 reviews

Condo in Crystal River

Crystal River Hideaway!

4.8 out of 5 average rating, 20 reviews

Condo in Dunnellon

River Retreat

4.99 out of 5 average rating, 134 reviews

A welcoming sign for Sawgrass Landing is surrounded by lush green landscaping and natural elements. The sign features decorative script and stylized plant graphics, indicating the entrance to the community.

Condo in Crystal River

Waterfront Condo in Sawgrass Landing

Other holiday rentals with a pool

An outdoor pool area is enclosed by a screened lanai, allowing for unobstructed views of the lush surroundings. Comfortable seating is positioned beside the heated pool, which reflects the sky, while the lawn offers a spacious, inviting atmosphere.

4.96 out of 5 average rating, 28 reviews

5BR Ocala Farm Home With Heated Pool, 6Min To WEC

An aerial view of the home showcases a spacious backyard with a screened-in pool area. The pool is surrounded by a concrete deck and lush green grass, while the house features a red roof and ample outdoor space for relaxation.

5 out of 5 average rating, 25 reviews

Welcome to Oasis Ocala!

A private pool area features clear blue water, with a sun shelf and steps leading out. White lounge chairs are positioned beside the pool. A wooden table with matching chairs provides outdoor dining options, all enclosed in a screened-in patio surrounded by trees.

4.92 out of 5 average rating, 37 reviews

Pam's Vacation Casa

An outdoor patio area features a glass table surrounded by four chairs. A pool is visible in the background, framed by well-maintained grass and trees. A charcoal grill is located to the right, providing a space for outdoor dining and relaxation.

4.93 out of 5 average rating, 28 reviews

Spacious 3 Bedroom Pool Home 1 mile from WEC

5 out of 5 average rating, 10 reviews

Townhouse in Ocala

Crownwood Modern New 3bd 2ba WEC equestrian FAST S

A refreshing pool is framed by a spacious patio featuring lounge chairs. Lush greenery surrounds the pool area, with a privacy fence in the background. Soft towels are neatly placed on the lounge chair, inviting relaxation under a bright blue sky dotted with clouds.

4.86 out of 5 average rating, 49 reviews

Villa turquesa, Very close to Silver Spring

4.89 out of 5 average rating, 19 reviews

The Poolside Paradise Retreat

A cozy living area features a green sofa, two blue armchairs, and a white coffee table. Natural light filters through large windows, illuminating the hardwood floor and a decorative area rug. A fireplace is situated beneath a minimalist mantel, enhancing the room's comfort.