Vacation rentals with a pool in Hernando County

Guesthouse in Brooksville

A wooden pathway leads towards a pool surrounded by greenery. Sturdy stairs ascend to the pool, which is partially shaded by trees. Potted plants add a touch of nature, while colorful inflatable toys rest nearby, creating an inviting atmosphere for relaxation.

4.97 out of 5 average rating, 36 reviews

Grandma’s Country Cottage

Welcome to Grandma's Country Cottage, a charming 1 bedroom, 1 bathroom guest house nestled on a sprawling 2.5-acre property in the serene town of Brooksville, Florida. This cozy retreat offers the perfect blend of comfort and tranquility in a picturesque country setting. Escape the hustle and bustle of everyday life and step into a space where time slows down. The cottage boasts a warm, inviting atmosphere with all the comforts of home. Surrounded by lush greenery and the gentle sounds of nature

5 out of 5 average rating, 18 reviews

Home in Dade City

Water's Edge - A Lakefront Oasis

A 10-acre private lakefront estate ideally located to explore both Tampa Bay & Orlando attractions. A scenic, tranquil & luxurious retreat from the city. Directly on Lake Dowling with great bass fishing. Fishing kayaks (3), dock with custom kayak launch, four bedrooms (2 primary suites), 3 full/2 half baths, lux fully equipped kitchen, heated pool, fire pit, games, library, washer/dryer, birdwatching & stargazing. Water’s Edge promises an unforgettable experience in a stunning natural setting.

A colorful mural of a butterfly brings vibrancy to the outdoor seating area. Teal chairs provide comfortable seating around a fire pit, which is surrounded by firewood. A bright yellow pillow with the text 'Sun & Games' adds a cheerful accent.

4.94 out of 5 average rating, 117 reviews

Heated Pool, King Bed Game Room, Near Weeki Wachee

Welcome to #SunandGames_FL. It’s all sun and games from the moment you arrive. Relax by the heated pool & soak up the sun during the day and sit by the fire table in the evening or go head 2 head in the game room w/ a foosball table, air hockey, arcade games and more. Located close to: 18 min to Pine Island Beach 15 min to Weeki Wachee Gardens. Kayak with the manatees 6 min to Oak Hills Golf Club 40 min to Crystal River National Wildlife Refuge 50 min to Tampa/Busch Gardens 90 min to Disney

4.97 out of 5 average rating, 115 reviews

A collage showcasing various aspects of the Moto Ranch. The center features a bright living area with high ceilings. Surrounding images display outdoor activities, including ATV riding, kayaking, cycling, and horseback riding, set amidst lush green landscapes.

Home in Brooksville

Fuel Your Passion, Epic Moto Ranch Factory Ride

Embark on your escape to the Moto Ranch at Croom; an unforgettable off-road & outdoor adventure in the heart of nature. Situated on a serene 5-acre compound inside Croom Motorcycle Area & Withlacoochee State Forest, this is your exclusive gateway to almost endless thrilling motorcycle/ATV trails, outdoor experiences like mountain biking, horseback riding, kayaking, etc. and best of all… endless natural beauty! ☑ Many modern amenities of home ☑ Private access to Croom’s trails ☑ Pets welcomed

A private heated pool is set within a screened patio, featuring a smooth gray deck. A ladder provides access to the water, which is surrounded by lounge chairs and a dining table with chairs. Large windows offer views into the home.

4.97 out of 5 average rating, 124 reviews

Weeki Wachee Springs heated pool home retreat

Relax with the whole family at this Weekie Wachee/Springhill Heated pool home. 5 minutes from the crystal clear springs of Weekie Wachee state park and Buccaneer Bay that has spring fed beach with water slides , tiki bars and mermaid shows. It’s also located 10-15 minutes from Rodgers Park located on the river where you can swim, kayak with manatees and enjoy fun family time! Also 15 minutes away is Pine Island Beach Park and SunWest Beach Park for skiing, wake boarding and obstacle course.

Superhost

A screened pool area features a sparkling blue pool, surrounded by lush greenery and palm trees. Comfortable loungers are positioned on the water's edge, inviting relaxation while enjoying views of the Gulf beyond. Sunlight filters through the screens, creating a bright and airy atmosphere.

Home in Hernando Beach

4.9 out of 5 average rating, 108 reviews

Oasis on the Gulf- screened heated pool & jacuzzi!

You are renting this ENTIRE Seascape Oasis home sitting on the Gulf, with private water views, screened pool and a private dock for your boat: 3BRs, 2 baths + office BR + living + kitchen + breakfast room + dining room + gym + screened patios + 1 boat dock + Laundry room. Escape to kayaking, scalloping, fishing, crabbing, biking, pool, Florida sunset all at this Seascape Oasis! 5 mins to Weeki Wachee, 1 hr to Tampa, 2 hrs to Disney, minutes to restaurants, boat rentals, Walmart....

The exterior of the home features a well-maintained lawn and a two-car driveway, with a sun design on the surface. A palm tree and shrubs add greenery around the entrance, which includes a decorative door and a small window. The garage door is situated to the left.

4.89 out of 5 average rating, 151 reviews

Florida Gulf Coast. Sunshine and warm breezes!

2 bedroom 2 bath home in a quiet neighborhood. private pool with privacy screen lanai. The house sleeps 6 comfortably. Master has queen and private bath. Guest room has queen and set of bunk beds. Amenities: Fully equipped kitchen, air conditioning, heating, washer & dryer, wifi, smart TV, patio furniture and gas grill. Great location! Busch Gardens and Tampa attractions 45 minutes away! Many other attractions, including beaches, only minutes away! This is a pet friendly home.

A screened-in pool area features a clear, inviting pool with a waterfall and soft blue water. Surrounding greenery provides privacy, while lounge chairs are positioned near the water. Sunlight filters through the mesh enclosure, creating a bright and airy atmosphere.

4.95 out of 5 average rating, 120 reviews

Spring Hill, Florida Quaint Paradise

The Retreat sleeps 4 guest comfortably. Our 2 bedroom, 2 bathroom home features a pool with a waterfall and fenced backyard. This quaint paradise will make you feel relaxed sitting by the pool enjoying a good book with a drink while you can hear the breeze going through the palms in the backyard. It’s located on a quiet street. But minutes away from different beaches, golf courses, shops and restaurants, attractions and parks.Something to do for the whole family.

Guest suite in Spring Hill

An enclosed patio area features a shimmering pool surrounded by a paved deck. Four lounge chairs are visible alongside the water, with a glass-top dining table and chairs positioned nearby, inviting relaxation in a tranquil outdoor setting.

4.97 out of 5 average rating, 65 reviews

Attached Private GuestHouse- Fenced Yard

We are slowly working on creating a more environmentally friendly home, from solar energy to providing shelter and food for pollinators. Come and enjoy our slowly evolving oasis, whether it's bathing in the pool, relaxing in the jacuzzi (small charge for heating), or napping on the hammock. Weeki Wachee Springs State Park, Weeki Wachee River, & Pine Island Beach are all within 15-minute drive. Clearwater, Tampa, and Ocala are all within an hour's drive!

Superhost

A shaded outdoor seating area features wicker furniture with dark cushions arranged around a low table. Overhead ceiling fans provide ventilation. A swimming pool is visible in the background, framed by a spacious lawn, ensuring a relaxed environment for leisurely gatherings.

4.78 out of 5 average rating, 152 reviews

*4 miles from Weeki Wachi Springs!*¤

Being just 4 miles away from Weechi Wachi Springs, you'll have easy access to one of the area's most captivating natural attractions. Spend your days exploring the springs, hiking the trails, and immersing yourself in the beauty of nature. Very centralized to LOTS of shopping, restaurants, and even less than a mile from the important stuff, COFFEE (if you dont like ours). Welcome to our home. Please treat it as your own. We hope you enjoy it!

4.97 out of 5 average rating, 109 reviews

A viewing deck equipped with several white chairs overlooks calm waterways. A small boat and two kayaks are visible at the dock, surrounded by lush reeds and gentle water reflections under a bright blue sky.

Home in Hernando Beach

NewlyRenovated• Saltwater Pool •Kayaks• Pedalboat

Discover the perfect spot for a fun-filled vacation with family and friends at Seaside Retreat! Nestled along the beautiful waterways of Hernando Beach, this waterfront getaway offers everything you need for relaxation and adventure. Whether you’re looking to unwind by the pool, paddle through the serene waters, or enjoy lively local entertainment, Seaside Retreat has it all. Book your stay today and make unforgettable memories by the water!!

A heated swimming pool is illuminated in a soft blue under a canopy. String lights create a warm environment above, while a patio umbrella provides shade. The area features a sleek surface, with reflections visible on the water's surface, ensuring a calming ambiance.