Holiday rentals with a pool in Ocala

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, 142 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!

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.

4.95 out of 5 average rating, 106 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!

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, 117 reviews

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.

4.95 out of 5 average rating, 116 reviews

A spacious lanai area is enclosed by a mesh screen, providing an unobstructed view of the inviting pool. The home features a simple roof design and is surrounded by a grassy area and trees, contributing to a peaceful outdoor setting.

Home in Citrus Springs

*HEATED POOL*NEAR RAINBOW RIVER & CRYSTAL RIVER*

FREE heated pool to 82° all winter long! Tasteful & comfortable furniture throughout! Spacious ranch style home that will comfortably sleep 10! Well stocked kitchen supplies & other items you may have forgotten! Extremely desirable pool & lanai area, perfect for hanging out! Great central location, close to Rainbow River, Three Sisters Springs, Weeki Wachee & Devil's Den. Quiet neighborhood, great to unwind at after a day of paddling with manatees, scalloping or even local airboat tours!

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.

4.84 out of 5 average rating, 103 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, 115 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, 116 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.

4.82 out of 5 average rating, 146 reviews

Hidden Treasure NE. Ocala Ft King. Pool.

"Hidden Treasure is a comfy 60s home with 4 bedrooms, two baths, large(130x250) FENCED yard, parking for vehicles and large built in pool. There is a guest suite on the property that can be booked for an additional fee. parking for large-scale vehicles behind guest house 220x40..room for horse trailers! dogs allowed with permission and additional fee dog.50$ no cats.swim at your own risk. 12 miles to WEC..cameras on home are non functional..guest house price negotiable.

4.92 out of 5 average rating, 137 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 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.

4.92 out of 5 average rating, 116 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 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.

4.92 out of 5 average rating, 152 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.

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, 126 reviews

Pet-friendly home w/ fire pit & BBQ grill

Welcome to your Ocala retreat - a peaceful space for families, friends & pups to relax, play, and reconnect! - Sleeps 9 | 3 bedrooms | 5 beds | 2 baths - Private outdoor pool (not heated) - Detached game room w/ pool table, arcade games - Screened lanai, fire pit, BBQ grill: gas & outdoor dining - Fully equipped kitchen, wifi & 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

4.77 out of 5 average rating, 26 reviews

Grand 1920s Estate with Pool, Spa, & Gym

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.

4.9 out of 5 average rating, 58 reviews

*No Service Fees* Ocala Equestrian Oasis w/Pool

An outdoor space features a pool surrounded by a concrete patio and a well-kept lawn. A gazebo with draping curtains offers shaded seating, while lounge chairs are positioned nearby. Lush trees are visible beyond the fence, providing a sense of privacy.

5 out of 5 average rating, 83 reviews

Peaceful Pool Home In Ocala

5 out of 5 average rating, 5 reviews

Backyard Oasis w/ pool & hot tub

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.

4.87 out of 5 average rating, 45 reviews

Villa turquesa, Very close to Silver Spring

4.72 out of 5 average rating, 29 reviews

A sunlit, single-story home is featured with a red-tiled roof and a light yellow exterior. Lush greenery surrounds the property, with palm trees and colorful shrubs enhancing the inviting entrance. A paved driveway extends toward the front door, complemented by large arched windows.

Home in Dunnellon

Pool/Spa Golf Course Community Home 190

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.

4.87 out of 5 average rating, 71 reviews

Cheerful 4 Bedroom Pet Friendly with Pool

4.78 out of 5 average rating, 9 reviews

COZY 3BR/2BAFamily home close to WEC &Silver Sprin

Apartment rentals with a pool

4.83 out of 5 average rating, 6 reviews

Apartment in Hernando

Citrus Hills Condo close to all amenities

Apartment in Crystal River

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, 194 reviews

Crystal River Bungalow with boat slip

An outdoor pool area is surrounded by lounge chairs in various shades of blue. A hot tub is adjacent to the pool, both set against a backdrop of lush greenery and water views. Umbrellas provide shade, enhancing the tranquil environment.

Apartment in Dunnellon

5 out of 5 average rating, 4 reviews

Riverside Retreat

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

Apartment in Crystal River

5 out of 5 average rating, 14 reviews

Crystal River Hideaway!

4.84 out of 5 average rating, 19 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

Apartment in Crystal River

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

5 out of 5 average rating, 25 reviews

Apartment in Hernando

2 Bedroom 2 Bath Condo with pool

Other holiday rentals with a pool

4.74 out of 5 average rating, 19 reviews

A spacious two-story house is set in a lush green landscape, surrounded by tall trees. A horse grazes in the fenced area of the property, and a large balcony can be seen on the upper level, offering views of the serene environment.

Farm stay in Ocala

New! Beautiful 10 acre Ocala farm w/sparkling pool

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, 23 reviews

Welcome to Oasis Ocala!

5 out of 5 average rating, 83 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

4.98 out of 5 average rating, 50 reviews

Home in Lady Lake

Relaxing House in The Villages

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, 27 reviews

Spacious 3 Bedroom Pool Home 1 mile from WEC

5 out of 5 average rating, 24 reviews

The private pool area is enclosed by a screened lanai, illuminated by string lights. A relaxing area features loungers beside the pool, with a raised spa and gentle water feature. Lush greenery surrounds the space, creating a serene atmosphere.

Villa in Lady Lake

Heated Pool Golf Cart Dog Friendly in The Villages

4.95 out of 5 average rating, 21 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