
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.

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.

Oceanfront Guest Favorite Balcony Pool Best View
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

"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.

This began as our paradise-Now it could be yours
Sleeps up to 5 very bright, open concept, ground floor, front unit, steps away from pool, kitchen fully stocked with ; dishes, glasses, flatware, pots, pans, new Keurig coffee maker, new blender, toaster, china cabinet in dining area kitchen cabinets, updated bathrooms bathroom towels provided, bedding for king size bed in master and 2 twin beds in 2nd bedroom, washer/dryer in condo.Walk in Shower , FRESHLY PAINTED, 2 rolls tolet paper 1 roll paper towel,(Remember this not a hotel )

STUNNING OCEANVIEW, Beachfront, internet 70" TV
Welcome to Daytona Beach Resort, where the majestic Atlantic Ocean steals the show. Immerse yourself in the gentle waves and warm Florida sun for an unforgettable getaway. Our stunning condo offers an extraordinary beachfront retreat with beach-style decor and breathtaking ocean views. Unwind in comfort with our fully furnished space and indulge in a cinematic experience with our 70" screen. But the real gem is the pristine beach just steps away from your doorstep.

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. 

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.

Ocean side condo Daytona beach, with sunset view.
Charming studio, King size bed. Equipped kitchen . Spacious bathroom w/ towels. The Daytona Beach Resort is on Daytona beach, close to Ormond Beach, Fabulous shopping, dining, & entertainment near by. The Studio faces the city of Daytona for spectacular sunsets. The indoor & outdoor north pools are open. The sauna and gym are also open. Please message with questions. parking is on the south side in the lot next door.
Popular amenities for Holly Hill rentals with a pool
House rentals with a pool

Ormond By TheSea Pool Retreat

Coastal Luxe Retreat | Team Joseph Ellen

Large lighted Pool, 8 min to beach, huge backyard

Heated Pool house 4 miles away from the beach

Endless Summer Oasis with a Pool

The Lemon Cottage -NO EXTRA FEES

Charming Coastal Retreat

COZY 2 BEDROOM HOME
Condo rentals with a pool

Beachfront Luxury with Spectacular Ocean Views!

Cozy condo on the beach

Daytona Escape

Victory Lane Ocean front Daytona Beach

Its a Vibe Beachfront Condo in Daytona Beach

Beautiful Ormond Beach Ocean Front Condo

Stunning Studio with Breathtaking Ocean Views

Glorious Oceanfront Escape: 1BR Private Balcony
Other vacation rentals with a pool

Daytona Beach Penthouse. Oceanfront Balcony + Pool

DB Stay ON THE BEACH + At Very Prime Fun Location

Luxury, Direct Oceanfront Condo

Ocean Front Extended Balcony Daytona Beach

Friendly Neighbor Suite

Amazing Oceanfront Condo On The Beach

Daytona Oceanside Inn Condo

*Oceanfront Penthouse Suite w/ Iconic Views
When is the best time to visit Holly Hill?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $219 CAD | $242 CAD | $255 CAD | $244 CAD | $244 CAD | $244 CAD | $244 CAD | $241 CAD | $223 CAD | $217 CAD | $181 CAD | $187 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 $84 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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- Ocean Center
- Daytona Beach Bandshell
- Daytona International Speedway
- Playalinda Beach
- University of Central Florida
- Ocala National Forest
- Daytona Boardwalk Amusements
- St Augustine Amphitheatre
- Summer Haven st. Augustine FL
- Wekiwa Springs State Park
- Lightner Museum
- 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
- Anastasia State Park
- Addition Financial Arena




