
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.

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 😎🌴

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. Walking distance to shopping and restaurants. House guests must have only registered guests on property, any violation causes removal and no refund. Only 2 miles to beachside. Our home away from home resort is the perfect place to find peace, tranquility and a short stay getaway.

INSTA-WORTHY Beach House! 📸 Pool 200ft from Beach!
Costal beach home 200ft. from pristine no-drive beach.. close to grocery, restaurants and entertainment. Large pool deck with new pavers. 2 sun loungers have been added along with fresh landscaping. Large swimming pool. Located on a quiet street, this 2BR/2 BA home is the perfect location to relax & live like a local. Perfect for families & friends, this place is fully stocked and ready for your arrival, just bring your swimsuit, flops & sunglasses.

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.

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

Waterfront Oasis w/ Private Pool – Relax & Unwind

Walk to Beach | Pool, Spa & Private Dock

Private Pool & Hot Tub - Walk to Flagler Ave

Heated Pool house 4 miles away from the beach

Patio Oasis! Heated Pool/Spa 2 acres-Top 1%Airbnb

COZY 2 BEDROOM HOME

Gorgeous Pool Home near Beaches-Pets OK

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

Luxury Beachfront Condo

Updated Oceanfront Condo! Come Relax by the Sea!

Beachfront Luxury with Spectacular Ocean Views!

Victory Lane Ocean front Daytona Beach

Its a Vibe Beachfront Condo in Daytona Beach

Escape 2 The Beach Daytona Beach FL 2BR 2B

Sea Woods Condo Near Pool and Beach | Bottom floor

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

SeaTurtle at Sea Fern - oceanfront!

Oceanfront Studio Oasis

Resort Studio w/ Beach Access & Ocean Views!

Scenic beachfront condo

*Oceanfront Penthouse Suite w/ Iconic Views

"Ocean Overload" w/huge private balcony POOL OPEN

Fantastic Ocean Front Condo with Amazing Views!

Waterfront Beach Family Home Heated Pool Game Room
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 | $250 CAD | $239 CAD | $239 CAD | $239 CAD | $239 CAD | $237 CAD | $219 CAD | $213 CAD | $178 CAD | $183 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
- Crescent Beach
- 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
- Saint Augustine Town Plan Historic District
- King's Landing
- Fountain of Youth Archaeological Park
- Blue Spring State Park
- Ravine Gardens State Park
- Embry Riddle Aeronautical University
- Orlando Speed World
- Historic Downtown Sanford
- Addition Financial Arena
- St. Augustine Alligator Farm Zoological Park
- Vilano Beach Fishing Pier




