Holiday rentals with a pool in Ocala

Farm stay in Crystal River

A small, brightly painted red barn home is surrounded by greenery, with Spanish moss hanging from nearby trees. An outdoor picnic table sits on a concrete path, and two Adirondack chairs are positioned nearby. A black structure is attached, offering shade and comfort.

4.98 out of 5 average rating, 154 reviews

Barn Style Tiny Home on Mini-Farm

Books fast! Manatee season! Tiny home on a rescue farm minutes to manatees, springs, rivers, and beaches! A refuge for fainting goats, ducks, chickens, baby piglets, an OUTDOOR hot/cold shower, and a COMPOST toilet. Adventures, fishing, while manatees, dolphins, and other wildlife can be spotted near year-round. Sit by a fire and relax in Adirondack chairs, hammock or at a picnic table. Bring water toys, kayaks, ATVs, RV/trailer, boats, and FUR BABIES for the ultimate GLAMPING getaway! Read all!

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.

4.93 out of 5 average rating, 138 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, 331 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.

4.98 out of 5 average rating, 418 reviews

The inviting exterior features a two-story home framed by lush green grass and mature trees. Arched windows and a symmetrical design enhance the charm, while a driveway leads to the front entrance, providing easy access to the peaceful surroundings.

Guest house in Leesburg

Silver Lake Guest Pool House Very Private !

The Silver Lake Pool Guest house Is your home away from home 1400 sq feet plenty of room! The pool house is a peaceful place to relax or take a swim in a large salt water pool . Mt Dora Tavares, Eustis 10 to 15 minutes away from Pool house Forty five minutes Daytona, Tampa Smyrna beach and parks Minutes from grocery stores restaurants malls Full kitchen also grilling. We are happy to help you with your needs ! Home is great for couples families, solo adventurers, and business travelers

A screened-in pool area is highlighted, featuring a sparkling blue pool surrounded by a stone patio. Greenery is visible beyond the enclosure, contributing to the serene environment. A single lounge chair is positioned beside the pool, evoking a relaxing atmosphere.

4.82 out of 5 average rating, 127 reviews

Spacious 3BR home with HEATED POOL in Ocala

Relax and hang out with the whole family in this beautiful Ocala house! Soak up some sun in the screened in pool and lounge chairs, or enjoy the mini basketball court and outdoor grill. Just 25 min to the World Equestrian Center, it’s the perfect oasis to stay in while you or your family compete. Enjoy some peace and quiet with a short 20 min drive to a vibrant downtown. Just 5 min to the Marion Oaks Community Center with tennis and other activities, there is something here for everyone!

5 out of 5 average rating, 204 reviews

A private courtyard features a shimmering pool surrounded by a colorful patio. Bright orange and red accents are visible on outdoor furniture, complemented by potted plants. A striped umbrella offers shade, while the adjoining home displays large windows and inviting hues.

Guest suite in Ocala

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.

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.

4.95 out of 5 average rating, 109 reviews

Ocala Oasis-3 Bedrooms and Heated Pool!

Relax in a safe neighborhood with a pool home that boasts 3 bedrooms and a game room with air hockey/pool/Foosball table. There is a outdoor Basketball hoop, ample pool side seating, fire pit, and kayaks for exploring The Silver Springs, which are 6 miles away. This home is spacious, quiet, and clean. Just minutes from downtown and 12 miles from World Equestrian Center. Have fun grilling by the pool or venturing out on the town. This home is central to everything Ocala has to offer.

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, 105 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!

4.97 out of 5 average rating, 115 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

Luxurious lakefront home on Lake Dora - 8 minutes to downtown Mount Dora and Tavares. Enjoy your vacation in this newly renovated pool home (Pool Not Heated) on Lake Dora and the Harris chain of Lakes. Bring your boat or rent one nearby to explore the area by water and cruise the Dora Canal to Lake Eustis. Included is a guest apartment with private entrance totaling 4 bedrooms and 4 full baths. Just a half mile to the Tavares Pavilion and dining in downtown Tavares.

4.89 out of 5 average rating, 243 reviews

A serene outdoor pool area is enclosed by a screened patio, featuring steps leading into the refreshing water. Lush greenery surrounds the pool, complemented by vibrant tropical plants. A decorative fountain adds a tranquil touch, enhancing the inviting atmosphere.

Home in Crystal River

Tropical Garden w/ Heated Pool* 3 mins Sis Spring

❤️Few Reasons Why Booked with us❤️ ➡️Amazing Tropical Private Backyard ➡️Clean Heated Pool ➡️BBQ / Fire Pit ➡️Private & Calm location ➡️Near Crystal River Attractions Indulge in an extraordinary getaway when you book this vacation rental. Located in the heart of Crystal River, yet secluded and private, with nearby access to beach and local amenities. Start your day with the sweet sounds of birds. This rental offers a range of amenities for your family's pleasure

4.91 out of 5 average rating, 126 reviews

Cottage in Clermont

Beautiful country house

Take the whole family to this fantastic place with many areas to have fun. We have 5 acres of land just for you, beautiful country house in the only hills of the state of Florida, you will enjoy the tranquility, privacy, connection with nature and you will witness a beautiful sunset unparalleled, stay and watch the stars, spaces suitable for unique souvenir photos. Ideal area for cycling and hiking. NOTE: if you want an event, check first for our rates

A fire pit is surrounded by four red adirondack chairs on a grassy yard. The area is spacious, featuring a circular stone border around the fire pit. Lush greenery and a wooden fence create a serene backdrop under a partly cloudy sky.

4.97 out of 5 average rating, 120 reviews

Pet-friendly home w/ pool & BBQ

Welcome to a peaceful Ocala retreat where you can slow down, spread out, and enjoy time together. - Sleeps 9 | 3 bedrooms | 5 beds | 2 baths - Private outdoor pool(not heated) - available all year - Detached game room w/ pool table & arcade games - Fully fenced backyard, fire pit & screened lanai - Indoor fireplace, 65” HDTV & dedicated workspace - Pet-friendly & family-ready w/ baby gear on request

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, 78 reviews

An outdoor space features a heated swimming pool beside a lanai. A table with chairs and a television is situated under the screened roof, while a hot tub is positioned nearby. Two inflatable rings float in the clear water, surrounded by potted plants.

Home in Citrus Springs

Private Spa *Heated Pool* & Firepit Near Manatees!

An enclosed patio features a heated saltwater pool, accentuated by stone tile and decorative mosaic. Nearby seating options are visible, including a lounge chair under a shaded canopy. Lush greenery surrounds the area, providing a sense of privacy and tranquility.

4.96 out of 5 average rating, 140 reviews

Villages-Private Heated Pool-Central Location

5 out of 5 average rating, 3 reviews

Vernon House - Pool Home in Downtown 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, 29 reviews

Stunning Private Oasis with Pool near WEC

An open-concept living space is featured with a modern kitchen equipped with stainless steel appliances and a seating island. A comfortable sectional sofa is positioned near a sleek coffee table, while a large wall-mounted TV offers entertainment options. Natural light fills the room, enhancing the inviting atmosphere.

5 out of 5 average rating, 7 reviews

Crownwood Modern New 3bd 2ba WEC equestrian FAST

The exterior of the home features elegant curved architecture, complemented by a vibrant red front door. Large arched windows allow natural light to fill the interior, while the well-manicured lawn and landscaping enhance the welcoming feel of the property.

4.86 out of 5 average rating, 88 reviews

Elegant Ocala Oasis w/Pool: Unwind in Luxury

4.95 out of 5 average rating, 42 reviews

Home in Crystal River

Waterfront~Dock~Kayaks | Pool | Manatees | Fishing

A screened pool area features a clear blue pool, with a colorful beach ball floating on the surface. Surrounding the pool, a tiled deck is equipped with lounge chairs, and the background includes the house and outdoor seating.

4.98 out of 5 average rating, 51 reviews

Ocala WEC & HITS Serenity Oasis

Apartment rentals with a pool

Apartment in Homosassa

4.94 out of 5 average rating, 16 reviews

Homosassa River Access: Snowbird's Paradise!

4.75 out of 5 average rating, 8 reviews

Apartment in Welaka

Riverfront, Fishing and Boating Paradise, Pool!

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.

4.83 out of 5 average rating, 182 reviews

Crystal River Bungalow with boat slip

5 out of 5 average rating, 3 reviews

Crystal River Hideaway!

4.33 out of 5 average rating, 3 reviews

A cozy living area features a beige sofa and a blue armchair, accompanied by a low coffee table. Vintage maps adorn the wall, complemented by decorative items. A ceiling fan and a standing plant add natural elements to the space, which is illuminated by soft lighting.

Apartment in Welaka

Sunset Getaway

An aerial view captures the community, highlighting a serene waterway bordered by trees. Several docks are visible alongside the water, with boats moored. Nearby, a diverse array of residences is situated, complemented by well-maintained landscaping and open spaces for recreation.

5 out of 5 average rating, 5 reviews

Breath Deep: Relax by the Water

4.82 out of 5 average rating, 17 reviews

A serene swimming pool area is framed by lush greenery and overlooks a calm body of water. Comfortable blue lounge chairs are arranged around the pool, complemented by potted plants. The clear sky and surrounding nature create a peaceful outdoor setting.

Apartment in Dunnellon

River Retreat

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.

4.99 out of 5 average rating, 134 reviews

Waterfront Condo in Sawgrass Landing

Other holiday rentals with a pool

5 out of 5 average rating, 28 reviews

The Palms. Luxurious, giant pool, golf, pond view

5 out of 5 average rating, 3 reviews

5-Star Luxury | Prime Location & Top Amenities

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, 26 reviews

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

5 out of 5 average rating, 81 reviews

A red wooden bench is positioned beside a small pond, where a fountain can be seen creating a gentle spray of water. Lush greenery surrounds the area, while a winding pathway leads towards the seating, enhancing the serene outdoor setting.

Guest house in Ocala

Orley farm guesthouse

4.94 out of 5 average rating, 16 reviews

A single-story villa is illustrated with a light gray exterior and a well-maintained lawn. The entrance, centered, features a white door, while an air conditioning unit is visible on the side. The sky is partly cloudy, creating a bright ambiance.

Flat in Ocala

SleepyOak-Cala

5 out of 5 average rating, 14 reviews

Heart of The Villages-guest pass for pool, golf

4.96 out of 5 average rating, 69 reviews

A spacious sleeping area features a full-size bed dressed in dark blue bedding. Two wooden armoires stand on either side, complemented by bedside tables. A chandelier illuminates the room from above, and two chairs are placed in front of a small table.

Flat in Ocala

Lovely apartment in the Heart of Horse Country.