
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.

Top Rated Best Views Oceanfront 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.

The Rider House Daytona | Pool |7 min to Beach
Stylish industrial 3BR/2BA private Florida home just 7 min from Daytona Beach. Private pool, fire pit, coastal-style bar, BBQ, gazebo, pool table, record player, Smart TV, high-speed WiFi, washer/dryer, full kitchen & keyless check-in. King, Queen & bunk beds. Located in a quiet neighborhood near the Speedway, outlets & dining. This isn’t a hotel stay, it’s a private space created for connection, downtime, and unforgettable Daytona moments. Book your stay and make it your next favorite memory

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

"Southern Comfort" Pool - Daytona & Ormond Beach
Nestled between the beaches of Daytona and Ormond, our vacation home has so much to offer! "Southern Comfort" is the prime location for some R&R or family adventure! Enjoy a BBQ by the POOL followed by a game of cornhole or spend the day walking the BEACH. Take in some excitement at DAYTONA INTERNATIONAL SPEEDWAY or sharpen your pickleball skills at PICTONA! Shop the TANGER OUTLETS or enjoy a dinner cruise on the HALIFAX RIVER! There's so much to do, you're just a short drive/walk to it all!

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.

Victory Lane Ocean front Daytona Beach
We are one of the closest airbnb to the boardwalk, OnThe Worlds Most Famous Beach with an open Pool 65inch Tv Come enjoy our Newly Furnished Studio with Amazing Top Floor Beach Views. We are the Closest AIRBNB on the Beach to the Daytona International Speedway With king bed and Queen sleeper sofa. Centrally located in the Heart of Daytona Beach. walking distance to the Pier Boardwalk, Restaraunts, and Main Street We have FREE parking for 1 vehicle and provide Coffee,Cream,Sugar,bch chairs.

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!

Large lighted Pool, 8 min to beach, huge backyard
Welcome to your tropical getaway in the heart of Daytona Beach! Located 3 miles from the beaches & 12 minutes from Nascar Speedway. This home includes a large swimming pool surrounded by a HUGE private yard, ping pong table, BBQ grill, 3 bedrooms, 4 beds, 2 bathrooms, & 1 premium queen airbed. Every room has Smart TVs & fast Wi-Fi (500 Mbps). Our fully stocked kitchen includes an air fryer, rice cooker, blender & more! Lastly, our quiet & safe neighborhood will ensure a peaceful stay 😎🌴

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.

Daytona’s paradise/bonfire/BBQ/3Bed/2Baths
Welcome to your perfect getaway! This beautiful, family-friendly home is nestled just minutes from the river, offering stunning views and a serene escape from the everyday. With a private pool, spacious layout, and plenty of amenities, this is the ideal spot for families and groups looking to relax and unwind. 1320 Daytona Avenue is situated in a prime location offers residents and visitors a variety of attractions and amenities within a short distance. 

Daytona Escape
Wonderful direct oceanfront condo steps from the beach. Sit on your own private balcony listening to the waves while enjoying your favorite beverage. We offer a new queen sized pillow top mattress ,rollaway bed and recliner sofa. We also have a new Samsung 55"smart TV with full cable lineup and 100 mps WIFI. The kitchen is fully equipped ,but if you prefer not to cook Adams Egg restaurant is located right on the property

Pool Party in Daytona! Sleeps 8
Enjoy the best of Daytona Beach in this spacious, modern pool home! It sleeps 8 comfortably and is just minutes from beaches, dining, top attractions, and local parks. Unwind in your own private backyard oasis featuring a sparkling pool and serene park views. Perfect for families or groups, this home offers the ideal blend of relaxation, privacy, and fun—no crowds, no stress, just your own slice of paradise.
Popular amenities for Holly Hill rentals with a pool
House rentals with a pool

Daytona Beach area, Port Orange pool home

Walk to Beach | Pool, Spa & Private Dock

Private Pool & Hot Tub - Walk to Flagler Ave

Heated Pool house 4 miles away from the beach

The Lemon Cottage -NO EXTRA FEES

Fun Beachside Home with Heated Pool & Golf Cart

COZY 2 BEDROOM HOME

Ocean to the front, River in the Back
Condo rentals with a pool

Luxury Beachfront Condo

Beachfront Luxury with Spectacular Ocean Views!

The Dancing Dolphin, a direct ocean front condo.

Perfect View Studio on Daytona Beach

Its a Vibe Beachfront Condo in Daytona Beach

Escape 2 The Beach Daytona Beach FL 2BR 2B

Coastal bliss.

Sea Woods Condo Near Pool and Beach | Bottom floor
Other vacation rentals with a pool

You deserve the Penthouse, treat yourself!

Oceanfront Studio Oasis

Resort Studio w/ Beach Access & Ocean Views!

Cloud Nine by the Sea ~Limited Amenities Open

Featured on TV “Making Waves” Oceanfront Penthouse

*Oceanfront Penthouse Suite w/ Iconic Views

Private Pool Oasis w/ Game Room & Outdoor Kitchen

Sophisticated Oceanfront Luxury Condo
When is the best time to visit Holly Hill?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $215 CAD | $238 CAD | $251 CAD | $240 CAD | $240 CAD | $240 CAD | $240 CAD | $237 CAD | $219 CAD | $214 CAD | $178 CAD | $184 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 $96 CAD per night before taxes and fees

Verified guest reviews
Over 1,770 verified reviews to help you choose

Family-friendly vacation rentals
20 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
40 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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- 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
- King's Landing
- Saint Augustine Town Plan Historic District
- Blue Spring State Park
- Ravine Gardens State Park
- Embry Riddle Aeronautical University
- Historic Downtown Sanford
- Orlando Speed World
- St. Augustine Alligator Farm Zoological Park
- Addition Financial Arena
- Vilano Beach Fishing Pier
- San Sebastian Winery




