Vacation rentals with a pool in Holly Hill

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Top-rated rentals with a pool in Holly Hill

Guests agree: these homes with a pool are highly rated for location, cleanliness, and more.

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Top guest favorite

A private balcony offers a relaxing view of the ocean, with two chairs positioned around a small table. The horizon features sailboats gliding over the water, while the sandy beach stretches below, framed by gentle waves under a clear sky.

Condo in Ormond Beach

4.97 out of 5 average rating, 115 reviews

Guest Favorite Direct Oceanfront Balcony Views

Steps from the sand, this 2 bed / 2 bath direct oceanfront condo offers amazing panoramic ocean views, a large balcony, and everything you need for a perfect stay. Enjoy free parking, your own free washer and dryer, a large newly renovated oceanfront pool, beach gear, and fast Wi-Fi. Sleeps 6 with comfy beds and 3 large streaming TVs. Located in a safe, quiet community near top attractions. We’ve thoughtfully included all the essentials to ensure a seamless getaway. Check out our 5-star reviews!

Top guest favorite

Home in Daytona Beach

4.98 out of 5 average rating, 44 reviews

Pool/Garage/Games/10 min drive to Bucees/Beaches

Enjoy your stay at this newly remodeled beautiful tropical oasis retreat where you can relax, work or play. Enjoy a large 65 inch TV in the living room couch/sofa bed and 40 inch tv’s in the master and guest bedroom. Plenty of entertainment, board games, ping pong table and a beautiful sunroom for your photo ops. Grill by the private pool area and soak in the sun at our deck. Laundry onsite. 10 Minute drive to the beaches and 15 minute drive to Daytona International Speedway! Sea you real soon!

Guest favorite

A private backyard features a pool and hot tub surrounded by lush greenery and palm trees. Lounge seating is positioned nearby, offering a relaxed atmosphere. A vibrant blue floating ball adds a pop of color to the clear water. Sunlight illuminates the space, enhancing its tranquil appeal.

Home in New Smyrna Beach

4.9 out of 5 average rating, 162 reviews

Private Pool & Hot Tub - Walk to Flagler Ave

Enjoy one of New Smyrna's very few rentals that offer a Private Pool and Hot Tub in the Heart of New Smyrna Beach. The back yard offers a private and peaceful setting to enjoy the Pool &Hot Tub. Great Location, Walk to Flagler Ave, where all the restaurants, shops and bars are located. Beach access is less than a 2 minute walk, just across the street. Beach chairs, towels, umbrellas, and a cooler are at the house for use. We have multiple units please contact host if you have a big group.

Top guest favorite

A cozy seating area features a floral-patterned futon, positioned beside mirrored walls and large windows that provide views of the ocean. Natural light fills the space, complemented by a floor lamp and decorative table lamp, enhancing the relaxing ambiance.

Condo in Ormond Beach

4.98 out of 5 average rating, 144 reviews

Oceanfront Studio - also the closest to the beach

Need time to rewind? Play on the beach or sit on the balcony in solitude and reflection! Beach and pool open! Safe, quiet building of only 33 units. No crowds! We have over 300 five star reviews for our two properties. Guarantee you the same experience in either unit! Same outstanding view! Same fast wifi! Same amenities!The ocean is directly in front of your studio. Condo is on the 3rd floor with queen size Murphy bed and a futon that opens to a full size bed & FULLY equipped kitchen.

Top guest favorite

An aerial view captures a serene beachfront scene, showcasing gentle waves lapping against soft sand. A pool area with several lounge chairs complements the expansive green space leading to wooden walkways that provide access to the beach.

Condo in Ormond Beach

5 out of 5 average rating, 138 reviews

Sea Forever -Oceanfront Getaway in Ormond Beach

Whether you are looking for a romantic getaway, a fun place to hang with good friends or a family vacation...Look no further, you have found the perfect spot. Come stay at "Sea Forever" where the ocean waves will help cure what ails you. Life is so good here. So much to do, Sun, Surf, Sand and Fun. A day trip to St. Augustine, Great Shopping and some of the very best seafood restaurants around. Enjoy the most spectacular sunrises on the east coast. Book it now. You will be so glad you did.

Superhost

Condo in Daytona Beach

4.75 out of 5 average rating, 107 reviews

Nautical wreck, Heated Pool! 2 BATH!,ocean view!

Enjoy a stylish experience at this centrally-located place. Just fully renovated and furnished and ready to be enjoyed by you. 675 sq/ft condo-tel with FULL kitchen and everything you need to enjoy your vacation. JUST BRING YOUR TOOTHBRUSH! Bedroom has its own bathroom and living room has its own so no disturbing your kids or friends at night time. Oceanfront complex and my condo has a nice side view of ocean from my 5th floor private balcony also from front door. 2 pools one is heated!

Top guest favorite

A screened-in pool area is featured, showcasing a sparkling blue pool surrounded by a spacious deck. Sunlight streams through the screen, highlighting lounge chairs positioned near the water. The background includes a white fence, ensuring privacy and enhancing the outdoor retreat feel.

Home in Ormond Beach

4.95 out of 5 average rating, 22 reviews

Walk to Beach – 3BR w/ Heated Pool & Fenced Yard

Step inside this welcoming 3BR home and enjoy spacious living areas, a stylish kitchen with quartz countertops, and dining spaces perfect for gathering. Outside, the fenced backyard invites you to relax in privacy, featuring a screened-in pool with optional heating (available October to April for an extra cost), a patio for morning coffee or evening drinks, and plenty of space to unwind. Just minutes from the no-drive beach and Romano Park, this retreat blends comfort and coastal adventure.

Superhost

A cozy studio space contains a spacious bed with textured linens and soft pillows. A cheerful couch is positioned near the window, which allows natural light to brighten the room. Two stylish lamps provide additional lighting, and a simple dining area is visible in the background.

Condo in Daytona Beach

4.71 out of 5 average rating, 59 reviews

Ocean’s One

Welcome to our updated and cozy condo by the beach, offering comfort and convenience. Enjoy beachside living with easy access to the ocean, providing the perfect backdrop for a relaxing getaway. While our unit does not boast a direct ocean view, the **proximity** to the beach can't be beat! Note: Our unit is modern and trendy, but the building is old and from the 1960s. We maintain a smoke-free space but there may be residual smoke odor in the hallways due to individuals smoking outside

Top guest favorite

An aerial view showcases The Real McCoy, highlighting the spacious outdoor area with an inviting pool surrounded by lounge chairs. The upper-level wraparound deck offers scenic views of the intercoastal waterway, while palm trees and well-maintained landscaping enhance the outdoor living space.

Home in Daytona Beach

5 out of 5 average rating, 32 reviews

Historical Daytona Gem | Pool | Intercostal Views!

Step into history at The Real McCoy, a pet-friendly, 6-bedroom retreat once owned by William “Bill” McCoy. Relax in the outdoor pool, enjoy water views from the wraparound deck, and challenge friends in the sunroom with air hockey and an arcade machine, or head to the living room for a game of pool. With a fully equipped kitchen, cozy living spaces, and easy access to Holly Hill Park’s boat ramp and trails, this home offers a perfect blend of fun, comfort, and adventure in Daytona Beach.

Guest favorite

The primary bedroom features a spacious bed with plush, patterned pillows and a soft throw blanket. Large glass doors allow natural light to enter and provide access to the balcony with ocean views. Soft curtains frame the doors, and stylish lamps are placed on bedside tables.

Apartment in Ormond Beach

4.86 out of 5 average rating, 103 reviews

Seaside Serenity: Stylish & Cozy Oceanfront Condo!

Welcome to our charming oceanfront beach condo in the enchanting town of Ormond Beach! Nestled in a tranquil setting, this idyllic retreat offers an unforgettable coastal getaway. Located in the peaceful neighborhood of Ormond Beach, you'll find an array of charming shops, delectable restaurants, and vibrant local attractions just a short drive away. Whether you're seeking outdoor adventures, or prefer exploring the rich history of the area, this town offers something for everyone.

Top guest favorite

A tranquil pool area is surrounded by a screened enclosure, showcasing a crystal-clear saltwater pool. Comfortable lounge chairs are positioned near the water, and lush greenery, including ferns and tropical plants, enhances the serene setting.

Guest suite in Lake Mary

4.96 out of 5 average rating, 347 reviews

Stylish & spa like Getaway - peaceful garden suite

Relax and unwind from your busy life in this serene and quiet getaway. We are located 5 minutes to shopping and dining in downtown Lake Mary in a beautiful and safe neighborhood. Enjoy the solar heated saltwater pool and the comfy outdoor lounge area, Enjoy the backyard with its mature trees and tropical flowers. The indoors come with a luxury and modern wellness bathroom. Soak in the oversized tub or reenergize in the stylish rainfall shower with inbuilt bench and mood lighting.

Guest favorite

A tranquil pool area is seen surrounded by palm trees, with ocean views in the background. Lounge chairs are positioned near the water's edge, and the pool features a gentle curve. Bright blue skies enhance the inviting atmosphere of the outdoor space.

Condo in Ormond Beach

4.96 out of 5 average rating, 106 reviews

Beautiful Ormond Beach Ocean Front Condo

Beautiful ocean front condo. Two bedrooms two bathrooms. Large master bedroom with new California king bed, private bath and balcony overlooking the Ocean. 2nd Bedroom has 2 single beds. Recently renovated including new bathroom, tvs, and new flooring in bedrooms and living areas. Wifi, Led TV's throughout, shaded balcony overlooks the ocean, beautiful private pool, on site laundry, close to area shopping and restaurants, including a Publix across the street no smoking