Vacation rentals with a pool in Holly Hill

Find and book unique homes with a pool on Airbnb

Top-rated rentals with a pool in Holly Hill

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

%{current} / %{total}1 / 1
Guest favourite
A private tropical pool area is framed by lush greenery and vibrant plants, complemented by a stone water feature. The sparkling water reflects sunlight, creating a serene atmosphere. Loungers are positioned nearby for relaxation, inviting guests to enjoy the tranquil setting.
Guesthouse in Port Orange
4.93 out of 5 average rating, 384 reviews

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.

Guest favourite
A compact kitchen area features modern black cabinetry and a wooden countertop. A stainless steel sink is visible, along with neatly arranged kitchen items. Stairs lead to a private sleeping area, illuminated by warm lighting, and a framed artwork is displayed on the wall.
Boat in Sanford
4.91 out of 5 average rating, 357 reviews

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.

Guest favourite
Condo in Ormond-by-the-Sea
4.97 out of 5 average rating, 135 reviews

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.

Guest favourite
The backyard area features a private pool surrounded by lush greenery and multiple lounge chairs. A contemporary decorative table is positioned between the chairs, while soft evening light enhances the relaxing ambiance of the space.
Home in Holly Hill
4.94 out of 5 average rating, 66 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!

Top guest favourite
Home in Flagler Beach
4.97 out of 5 average rating, 127 reviews

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

Guest favourite
A bright and airy living area features large windows showcasing stunning ocean views. A white leather sofa sits on polished wooden flooring. A round table with chairs is positioned near the window, complemented by a decorative indoor plant adding a touch of greenery to the space.
Condo in Daytona Beach
4.94 out of 5 average rating, 194 reviews

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

Top guest favourite
A bright living area is visible with a light-colored sectional sofa facing a large sliding glass door that opens to a balcony. A blue accent wall features artwork of a heron. A wooden console table holds decor items, and a ceiling fan is present for comfort.
Condo in Ormond-by-the-Sea
5 out of 5 average rating, 150 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
A sunlit outdoor space features a circular pool surrounded by a wooden deck. Two lounge chairs are positioned nearby, accompanied by a small table and chairs. Lush greenery and palm trees create a natural backdrop, enhancing the relaxation area.
Home in Seabreeze Historic District
4.89 out of 5 average rating, 159 reviews

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!

Top guest favourite
A spacious studio room is seen, featuring a queen bed with a patterned coverlet and a twin bed that can be converted to a king. Light filters in through large windows, illuminating the room. There is a plush area rug on the floor, adding comfort.
Condo in Daytona Beach
4.88 out of 5 average rating, 177 reviews

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.

Top guest favourite
Apartment in Daytona Beach
5 out of 5 average rating, 100 reviews

*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!

Guest favourite
The image features an oceanfront view from a balcony. A glistening swimming pool is situated below, surrounded by palm trees and lounge chairs. The sunlight reflects off the calm ocean waters in the background, creating a serene atmosphere.
Condo in Ormond-by-the-Sea
4.86 out of 5 average rating, 164 reviews

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.

Guest favourite
Home in Holly Hill
4.95 out of 5 average rating, 106 reviews

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

When is the best time to visit Holly Hill?

MonthJanFebMarAprMayJunJulAugSepOctNovDec
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. temp15 °C16 °C18 °C21 °C24 °C27 °C28 °C28 °C27 °C24 °C19 °C17 °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

Destinations to explore