Short-Term Rentals in Cypress Head, FL: Compare 10+ Sites & Save

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  4.  Florida
  5.  Daytona Beach
  6.  Cypress Head

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382 Best Short-Term Rentals in Cypress Head (Starting from $95)

The Aviators Dream Pool, Spa and Private Runway!
The Aviators Dream Pool, Spa and Private Runway!
House
Port Orange, FL, USA
3.0k from Cypress Head center

Accommodations, Pools, Parking, Villas, Vacation homes, Cottages, Lodgings, Vacation rentals, Beach

3 Bedrooms6 Guests
New to Booking
$1092
Average price / night
Check Availability
Enjoy the Daytona 500 or Bike Week w/ friends at this Port Orange 5 bed home.
Enjoy the Daytona 500 or Bike Week w/ friends at this Port Orange 5 bed home.
House
Port Orange, FL, 32128, United States
2.1k from Cypress Head center

AC, Dryer, Free Parking, Heater, Internet, Kitchen, Laundry, Patio, Pool

5 Bedrooms15 Guests
10.0

Exceptional

2 reviews

$450
Average price / night
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Marvelous Memories
Marvelous Memories
House
Port Orange, FL, USA
3.5k from Cypress Head center

Accommodations, Villas, Vacation homes, Cottages, Lodgings, Places to stay

3 Bedrooms5 Guests
New to Booking
$245
Average price / night
Check Availability
Pool side in Port Orange, Near beach, Gated Community, Bikers Welcome!Golf!
Pool side in Port Orange, Near beach, Gated Community, Bikers Welcome!Golf!
House
Port Orange, FL, 32128, United States
2.2k from Cypress Head center

AC, Barbecue, Dryer, Fireplace, Free Parking, Heater, Internet, Kitchen, Laundry

4 Bedrooms8 Guests
9.2

Superb

43 reviews

$502
Average price / night
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New Smyrna Beach Vacation Rental with Pool Access
New Smyrna Beach Vacation Rental with Pool Access
House
New Smyrna Beach, FL, USA
3.8k from Cypress Head center

Accommodations, Pools, Parking, Villas, Vacation homes, Cottages, Lodgings, Vacation rentals, Places to stay

5 Bedrooms10 Guests
New to Booking
$177
Average price / night
Check Availability
Luxurious 4 Bedroom Home on Taxiway in Spruce Creek Fly-in, 6 miles to beach!
Luxurious 4 Bedroom Home on Taxiway in Spruce Creek Fly-in, 6 miles to beach!
House
Port Orange, FL, 32128, United States
2.3k from Cypress Head center

AC, Arcade, Barbecue, Crib, Dryer, Fireplace, Free Parking, Heater, Hot Tub

4 Bedrooms9 Guests
9.6

Exceptional

5 reviews

$557
Average price / night
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7 Mi to Beach Pet-Friendly Home in Port Orange!
7 Mi to Beach Pet-Friendly Home in Port Orange!
House
Port Orange, FL, USA
4.3k from Cypress Head center

Accommodations, Parking, Villas, Vacation homes, Cottages, Pet-friendly, Lodgings, Vacation rentals, Places to stay

4 Bedrooms8 Guests
New to Booking
$176
Average price / night
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3-bedroom house in Airport Community
3-bedroom house in Airport Community
House
Port Orange, FL, 32128, United States
2.4k from Cypress Head center

AC, Barbecue, Dryer, Free Parking, Heater, Hot Tub, Internet, Laundry, Microwave

3 Bedrooms6 Guests
New to Booking
$358
Average price / night
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Brae Burn by Ocean Properties
Brae Burn by Ocean Properties
House
New Smyrna Beach, FL, USA
4.5k from Cypress Head center

Accommodations, Pools, Parking, Villas, Vacation homes, Cottages, 4-star, Lodgings, Places to stay

2 Bedrooms7 Guests
New to Booking
$126
Average price / night
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Spruce Creek Fly-in Community, 24 hr Security gated Community/ inground pool
Spruce Creek Fly-in Community, 24 hr Security gated Community/ inground pool
House
Port Orange, FL, 32128, United States
2.5k from Cypress Head center

AC, Barbecue, Dryer, Fireplace, Fitness Equipment, Free Parking, Heater, Hot Tub, Internet

3 Bedrooms6 Guests
10.0

Exceptional

22 reviews

$358
Average price / night
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Pool and Hot Tub - Under The Sea
Pool and Hot Tub - Under The Sea
House
Port Orange, FL, USA
4.7k from Cypress Head center

Accommodations, Villas, Vacation homes, Cottages, Pet-friendly, Lodgings, Places to stay, Family

1 Bedroom6 Guests
New to Booking
$393
Average price / night
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Family Pool House • Sleeps 8 • Space to Relax
Family Pool House • Sleeps 8 • Space to Relax
House
Port Orange, FL, 32128, United States
2.7k from Cypress Head center

AC, Dryer, Heater, Internet, Laundry, No Smoking, Washer

4 Bedrooms8 Guests
New to Booking
$466
Average price / night
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Linda’s Lizard Landing
Linda’s Lizard Landing
House
Port Orange, FL, USA
4.8k from Cypress Head center

Cheap, Accommodations, Pools, Villas, Vacation homes, Cottages, Pet-friendly, Lodgings, Places to stay

4 Bedrooms9 Guests
9.6

Exceptional

5 reviews

$233
Average price / night
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Secluded Pondview Fly-In Haven
Secluded Pondview Fly-In Haven
House
Port Orange, FL, 32128, United States
2.8k from Cypress Head center

AC, Dryer, Heater, Hot Tub, Internet, Kitchen, Laundry, Microwave, No Smoking

3 Bedrooms6 Guests
New to Booking
$509
Average price / night
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Gray Sands Retreat
Gray Sands Retreat
House
Port Orange, FL, USA
6.0k from Cypress Head center

Accommodations, Pools, Villas, Vacation homes, Cottages, Pet-friendly, Lodgings, Places to stay, Accessible hotels

2 Bedrooms4 Guests
New to Booking
$220
Average price / night
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Relaxing 4-bedroom Pool Oasis Near Daytona
Relaxing 4-bedroom Pool Oasis Near Daytona
House
Port Orange, FL, 32128, United States
2.8k from Cypress Head center

AC, Barbecue, Fireplace, Free Parking, Heater, Hot Tub, Internet, Laundry, Microwave

4 Bedrooms8 Guests
8.0

Good

1 reviews

$376
Average price / night
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Waterfront home, luxury design, HOT TUB
Waterfront home, luxury design, HOT TUB
House
Port Orange, FL, USA
6.2k from Cypress Head center

Luxury, Accommodations, Parking, Villas, Vacation homes, Cottages, Lodgings, Jacuzzis, Places to stay

3 Bedrooms8 Guests
New to Booking
$794
Average price / night
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Executive 3-Bedroom Hangar Home within Spruce Creek Fly-In, live 24 hr security.
Executive 3-Bedroom Hangar Home within Spruce Creek Fly-In, live 24 hr security.
House
Port Orange, FL, 32128, United States
2.8k from Cypress Head center

AC, Barbecue, Dryer, Fireplace, Free Parking, Heater, Hot Tub, Internet, Kitchen

3 Bedrooms6 Guests
10.0

Exceptional

16 reviews

$459
Average price / night
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Cozy Home Near Ocean and Daytona Intl Speedway
Cozy Home Near Ocean and Daytona Intl Speedway
House
Port Orange, FL, USA
6.2k from Cypress Head center

Cheap, Accommodations, Pools, Parking, Villas, Vacation homes, Cottages, Lodgings, Vacation rentals

3 Bedrooms6 Guests
9.0

Fabulous

2 reviews

$219
Average price / night
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New! The Landing Pad-4 lrg BR-private heated pool-Reno-FlyIn-Golf-near Daytona
New! The Landing Pad-4 lrg BR-private heated pool-Reno-FlyIn-Golf-near Daytona
House
Port Orange, FL, 32128, United States
3.0k from Cypress Head center

AC, Barbecue, Dryer, Fireplace, Fitness Equipment, Free Parking, Heater, Internet, Kitchen

4 Bedrooms8 Guests
New to Booking
$507
Average price / night
Check Availability
Top Elegance and Fun DLuxx Home Windsor Cay 16101
Top Elegance and Fun DLuxx Home Windsor Cay 16101
House
Port Orange, FL, USA
6.3k from Cypress Head center

Accommodations, Pools, Parking, Villas, Vacation homes, Cottages, Lodgings, Places to stay

5 Bedrooms12 Guests
New to Booking
$345
Average price / night
Check Availability
Exclusive Spruce Creek 4BR Home w/ Pool & 24/7 Security
Exclusive Spruce Creek 4BR Home w/ Pool & 24/7 Security
House
Port Orange, FL, 32128, United States
3.0k from Cypress Head center

AC, Barbecue, Dryer, Free Parking, Heater, Internet, Kitchen, Laundry, Living Area

4 Bedrooms8 Guests
10.0

Exceptional

62 reviews

$516
Average price / night
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Cozy one bedroom
Cozy one bedroom
Apartment
Port Orange, FL, USA
6.4k from Cypress Head center

Apartments, Cheap, Accommodations, Pools, Parking, Lodgings, Places to stay, Family, Self-catering

1 Bedroom4 Guests
9.4

Superb

5 reviews

$95
Average price / night
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The Aviator's Dream: Pool, Spa & Private Runway!
The Aviator's Dream: Pool, Spa & Private Runway!
House
Port Orange, FL, 32128-6716, United States
3.0k from Cypress Head center

AC, Arcade, Balcony, Dryer, Extra Bed, Fireplace, Fitness Equipment, Free Parking, Heater

3 Bedrooms6 Guests
9.4

Superb

12 reviews

$585
Average price / night
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Coastal Cottage Near the Ocean
Coastal Cottage Near the Ocean
House
Port Orange, FL, 32127, United States
3.2k from Cypress Head center

AC, Barbecue, Dryer, Fireplace, Free Parking, Heater, Internet, Laundry, Microwave

4 Bedrooms8 Guests
10.0

Exceptional

5 reviews

$472
Average price / night
Check Availability
7 Mi to Beach! Poolside Oasis in Port Orange
7 Mi to Beach! Poolside Oasis in Port Orange
House
Port Orange, FL, 32127, United States
3.2k from Cypress Head center

AC, Crib, Dryer, Fireplace, Free Parking, Heater, Kitchen, Microwave, No Smoking

3 Bedrooms8 Guests
10.0

Exceptional

1 reviews

$273
Average price / night
Check Availability
Beautiful 3 Bedroom Condo w/ Golf in Luxury Community with Amenities
Beautiful 3 Bedroom Condo w/ Golf in Luxury Community with Amenities
Condo
Port Orange, FL, 32128, United States
3.2k from Cypress Head center

AC, Barbecue, Dryer, Fireplace, Free Parking, Heater, Internet, Laundry, Living Area

3 Bedrooms6 Guests
10.0

Exceptional

1 reviews

$220
Average price / night
Check Availability

Pro Tip:
VacationByOwnerRentals aggregates the best inventory from leading travel sites, including Booking.com, Agoda.com, Expedia.com, Vrbo.com, and Airbnb.com. Use our Advanced Filters to compare verified homes, villas, cabins, condos, cottages, vacation rentals, hotels, and eco-friendly stays. Our goal is to help you find the absolute best Short-Term Rentals in Cypress Head.

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Cypress Head Short-Term Rentals on the Map

Frequently Asked Questions

You can explore 382 verified short-term rentals in Cypress Head, including apartments, houses, and furnished stays suitable for both travel and temporary living.

Short-term rental prices in Cypress Head vary depending on location, property size, and travel dates. Rates typically start from around $95 per night, with higher prices for premium properties or peak seasons.

Many short-term rentals in Cypress Head include Wi-Fi, making them suitable for remote work. Some listings also provide dedicated workspaces, but it is recommended to check property details for specific features.

Booking 30 to 45 days in advance is generally recommended for the best availability. For peak travel periods or major events in Cypress Head, booking earlier can help secure better options.

In many cases, utilities such as electricity, water, and internet are included in the rental price. However, this can vary by property, so it is important to review the listing details before booking.

Short-term rentals in Cypress Head often include amenities such as Fireplace/Heating, Pool, and Laundry, providing a comfortable and convenient stay.

Short-term rentals in Cypress Head are often used for flexible stays, including work trips or temporary housing, while vacation rentals are typically geared toward leisure stays in tourist areas. Both offer furnished, home-like accommodations.