
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.

Relaxing Tropical Pool Get Away Suite
Relaxing Tropical themed pool, spa with grilling area and tiki bar. Private secure parking space near detached suite with gated entry code access. Centrally located to all main area attractions and events. Coffee, shopping, and walking distance from the popular local restaurants and drinking establishments, also two waterfront dog walking parks in the neighborhood. Only 2 miles to beachside. Our home away from home resort is the perfect place to find peace, tranquility and a short stay getaway.

Unique Concrete House Boat! No cleaning fees!
This ferrocement boat Later Gator was made in Sweden in 1973. That’s right! It’s made of concrete! The boat circumnavigated the globe twice before eventually ending up here in sunny Sanford FL. We spent 2 years completely renovating everything and tried to leave as much of the boat’s original personality intact while adding modern amenities. Restaurant/bar, pool, laundry facilities, showers and restrooms, diner, and marina store all on site, and downtown historic Sanford and river walk close by.

The Views! Oceanfront Guest Favorite Balcony Pool
Just steps from the beach, this bright and spacious 2-bedroom, 2-bath direct oceanfront condo is your perfect coastal getaway. Wake up to panoramic ocean views, sip coffee on the large private balcony, and fall asleep to the sound of the waves. The condo is fully equipped including beach chairs and gear, washer and dryer, ultra-fast Wi-Fi, and free parking. Enjoy a newly renovated oceanfront pool, comfortable beds for up to six guests, and three large smart TVs for streaming your favorite shows.

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!

Walk to Beach | Pool, Spa & Private Dock
This isn’t just a beach house — it’s your private coastal escape. Start your morning with coffee and a short walk to the beach. Spend the day poolside or out on the water, then unwind in the spa as the sun sets over the intracoastal. 👉 A perfect mix of beach days and relaxing waterfront evenings. 📍 Location • Walk to beach • Short drive to Flagler Beach restaurants & shops • Quiet, private neighborhood Centrally located between St. Augustine and Daytona Beach -35 minutes LBTR #37009

Breathtaking Ocean View Suite w/ Spacious Balcony!
NOTICE–Amenity Update Our building has been undergoing repairs. Some amenities have now reopened, while others remain closed as work continues. Currently Open: • 1 Outdoor Heated Pool • 1 Indoor Pool • 1 Hot Tub • Fitness Center & Sauna Still Under Repair: • Additional Outdoor Pools • Beach Access from the Pool Deck (Beach access is available via the North Side Beach Access) • Covered Parking Garage (Free parking is available in our south side parking lot) Thank you for your understanding

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.

Cowboy Pool | Mini Golf | Beach | Ocean Center
PET & BIKER FRIENDLY! Come stay at our tropical oasis just 1 block to the beach, steps from the Ocean Center & 1 street from Main Street! Whether you are in town for business, a convention at the Ocean Center or coming to enjoy the beach, our home is perfectly suited for all types! Bring your bathing suit & flip flops, we have taken care of the rest! Disney World & Universal Studios are 1hr & 15mins away! St Augustine(The first city in the US!) is only 1hr away! Take a day to explore!

Beachfront! Clean City view Studio & beach gear!
Queen and a twin bed that opens to king, stocked with beach gear. We offer beach chairs, umbrella, boogie boards and more for 2. On the beach with city view. Max 4, no pets. No smokers. Light cooking only. No children under 10. WARNING: Resort’s garage and sea wall are not operational Access to beach is adjacent to resort on North side, right next to our beautiful BEACH FRONT POOL! Parking lot is on the South side. We are N Daytona Beach, almost Ormond Beach.

*New* Pool Open! Direct Oceanfront 1 Bdrm King Bed
Just opened! Welcome to Daytona Beach Bliss! Enjoy our newly remodeled one bedroom condo with amazing oceanfront views from the 7th floor. Catch the sunrise in the morning on the balcony and you might even spot some dolphins! Relax at the beach, we are just steps away with our private beach access! Or spend some time in the heated oceanfront pool and hot tub. Beach towels, a cooler, two beach chairs, and a beach umbrella are provided for you!

Ormond Beach oceanfront condo
Top-floor oceanfront condo perfect for families. Enjoy stunning balcony views, two bedrooms, two baths, and comfortable space for six. Steps to the beach, pool, and elevator—vacation is effortless here. Fully equipped kitchen, cozy living area, and walkable dining and shops nearby. Relax with ocean breezes and sunrise mornings. Elegant coastal decor adds a touch of luxury. Create lasting memories in comfort and style. Your beach escape awaits.

Riverfront Retreat | Pool & Hot Tub near Beach
Escape to this coastal retreat with all the perks of waterfront living. Enjoy a riverfront resort-style pool with a full-size sun shelf and spacious, serene hot tub. Take in skyline and river views from the 30’ master suite balcony. Watch dolphins, manatees, and herons from the backyard. Only 5-10 minutes to Daytona Beach, the Speedway, Ocean Center, Pictonia, downtown, shops, dining & more!
Popular amenities for Holly Hill rentals with a pool
House rentals with a pool

Beachy Oasis! Close to New Smryna & Daytona Beach

Heated Pool house 4 miles away from the beach

The Lemon Cottage -NO EXTRA FEES

Guests Rave: Thoughtful Details & Super Clean

Historical Gem! | Large Pool | Intracoastal Views!

The Great Escape! Explore,Romance, Rest,Relaxation

Pool Home Near Parks & Beach Great Location

Heated Pool Home Paradise on Lake
Condo rentals with a pool

Beachfront Luxury with Spectacular Ocean Views!

Daytona Escape

Oceanfront Studio Oasis

Ocean Front in Ponce Inlet (Daytona / New Smyrna)

Oceania Getaway New Smyrna Beach, Florida

Its a Vibe Beachfront Condo in Daytona Beach

*Oceanfront Penthouse Suite w/ Iconic Views

Beautiful Ormond Beach Ocean Front Condo
Other vacation rentals with a pool

Oceanfront Private Patio-Pool/Hot Tub-Aruba #106

🏖 Ocean Front 21st Floor Vacation Paradise!!

Salty Shoals - Private Deep Water Dock Home w/Pool

Updated oceanfront 2/2 with balcony & heated pool

Gorgeous Pool Home near Beaches-Pets OK

VSBeachHaus

Fully-renovated oceanfront apt with private pool

The Royal Palm
When is the best time to visit Holly Hill?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $217 CAD | $241 CAD | $253 CAD | $242 CAD | $242 CAD | $242 CAD | $242 CAD | $239 CAD | $221 CAD | $216 CAD | $180 CAD | $186 CAD |
| Avg. temp | 15 °C | 16 °C | 18 °C | 21 °C | 24 °C | 27 °C | 28 °C | 28 °C | 27 °C | 24 °C | 19 °C | 17 °C |
Quick stats about vacation rentals with a pool in Holly Hill

Total vacation rentals
Explore 50 vacation rentals in Holly Hill

Nightly prices starting at
Holly Hill vacation rentals start at $83 CAD per night before taxes and fees

Verified guest reviews
Over 1,660 verified reviews to help you choose

Family-friendly vacation rentals
30 properties offer extra space and kid-friendly amenities

Pet-friendly vacation rentals
Find 10 rentals that welcome pets

Rentals with dedicated workspaces
20 properties have a dedicated workspace

Wifi availability
50 of Holly Hill vacation rentals include wifi access

Popular amenities for guests
Guests love Kitchen, Wifi, and Pool across Holly Hill rentals

4.7 Average rating
Holly Hill stays receive an average rating of 4.7 out of 5 from guests
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- Rentals with pools Volusia County
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- Rentals with pools United States
- Ocean Center
- Daytona Beach Bandshell
- Daytona International Speedway
- Playalinda Beach
- University of Central Florida
- Ocala National Forest
- Daytona Boardwalk Amusements
- St Augustine Amphitheatre
- Wekiwa Springs State Park
- Lightner Museum
- Summer Haven st. Augustine FL
- Daytona Lagoon
- Fountain of Youth Archaeological Park
- Blue Spring State Park
- Saint Augustine Town Plan Historic District
- King's Landing
- Ravine Gardens State Park
- Embry Riddle Aeronautical University
- Historic Downtown Sanford
- St. Augustine Alligator Farm Zoological Park
- Orlando Speed World
- Vilano Beach Fishing Pier
- Addition Financial Arena
- Anastasia State Park




