Discover Your Perfect Cypress Head Vacation Homes

Cypress Head Luxury Rentals

See More Cypress Head Luxury Vacation Rentals
Find More Cypress Head Villas, Resorts, & Rentals on BedroomVillas

Cypress Head Pet Friendly Vacation Rentals

See More Pet-Friendly Vacation Rentals in Cypress Head on PetFriendly.io

Cypress Head Large Vacation Homes

See More Family Vacation Rentals in Cypress Head on FVR

Why Choose Rent By Owner for your Cypress Head Vacation Rental Homes?

What makes our Vacation Rentals special?

image
Verified Listings
Book with confidence knowing every property meets our quality and safety standards.
image
Unbeatable Value
Enjoy competitive pricing with no hidden fees, providing exceptional value for every stay.
image
Diverse Options
From cozy cabins to luxurious villas, find a rental that suits your style and needs.

Popular Areas for Cypress Head Vacation Rentals

Where are the best neighborhoods to stay in Cypress Head?

When considering where to stay in Cypress Head, Port Orange, Florida, you’ll find a peaceful residential neighborhood that offers convenient access to local amenities and the charm of Florida’s Atlantic coast. This area provides a comfortable environment ideal for those seeking a relaxed, yet accessible, setting for their visit. Whether you're exploring nearby attractions or simply enjoying the serene surroundings, choosing a vacation rental in Cypress Head ensures a dependable and enjoyable experience during your stay in Port Orange. Discover the perfect home base in this welcoming community to make your Florida vacation truly memorable.

Waters Edge

Located in the scenic region of Port Orange, Waters Edge offers a tranquil setting for your stay with easy access to local waterways and natural beauty. Here, you can enjoy a peaceful retreat while remaining close to the area's amenities and attractions.

View 42+ Rentals in Waters Edge

Best Times to Visit Cypress Head

When should you plan your Vacation Rentals stay?

Timing your visit to this charming destination can enhance your experience, so consider planning your stay during the seasons when the area’s weather and local events align perfectly with your vacation goals.

Peak Season Highlights

spring
Spring (March to May)

During spring, you can enjoy warm weather and blooming landscapes which make this time ideal for outdoor activities in this region.

Average Temperature Daytime: 75-85°F - Nighttime: 55-65°F
summer
Summer (June to August)

Summertime offers hot temperatures and longer days, perfect for enjoying the beaches and water-based activities that draw visitors here.

Average Temperature Daytime: 85-90°F - Nighttime: 70-75°F

Off-Season Highlights

image
Fall (September to November)

In fall, the area experiences cooler temperatures and fewer tourists, making it a peaceful time to explore with comfortable weather conditions.

Average Temperature Daytime: 70-80°F - Nighttime: 50-60°F
image
Winter (December to February)

Winter months bring milder temperatures and less crowded surroundings, providing a tranquil setting for your stay in the region.

Average Temperature Daytime: 60-70°F - Nighttime: 40-50°F

Weekly Weather Forecast for Cypress Head

How to Book Your Cypress Head Vacation Rental Home

What's our booking process?

Our platform allows you to browse a curated selection of vacation rentals. Once you find the ideal property, you’ll be redirected to a trusted booking partner to complete your reservation securely.

Booking Steps

01

Search Properties

Use our filters to find the right property that fits your needs.
02

Select a Rental

Click on your preferred listing to view details, amenities, and pricing.
03

Book Online

Follow the link to finalize your reservation directly on the partner’s website.

Explore and book the perfect rental in Cypress Head

More Top-Rated Vacation Rentals in Cypress Head Area

Common Vacation Rentals Amenities

What amenities can you expect?

Our Vacation Rentals are designed to offer all the comforts of home, often with added perks to make your stay unforgettable. Here’s some common amenities to look forward to:

Indoor Features

  • Fully-equipped kitchens with modern appliances
  • Comfortable living areas with flat-screen TVs
  • Free Wi-Fi for staying connected
  • Air conditioning and heating for year-round comfort
  • In-unit washers and dryers for convenience
  • Luxurious bedrooms with premium bedding
  • Spa-like bathrooms with soaking tubs or walk-in showers

Outdoor Amenities

  • Enjoy access to a private outdoor swimming pool in your vacation rental, perfect for relaxing and cooling off during warm Florida days.
  • Take advantage of spacious outdoor patios or decks ideal for al fresco dining and entertaining guests.
  • Benefit from well-maintained landscaped gardens that provide a peaceful backdrop to your outdoor experience.
  • Utilize outdoor grills or barbecue facilities to prepare meals while enjoying the pleasant weather here.
  • Make use of a common community area with amenities such as shaded picnic spots or seating areas.
  • Explore nearby walking or biking trails that offer scenic views and promote outdoor activity within the region.
  • Relax in a screened-in lanai or veranda, providing a comfortable outdoor space protected from insects while you unwind.

Top Attractions Around Cypress Head

What attractions are nearby?

Nearby, you can enjoy a variety of outdoor activities, recreational parks, and scenic nature spots that showcase the beauty of this region, making your stay in Cypress Head truly memorable.

image
image

Family Activities

  • Port Orange Beach Adventures: Discover family-friendly beaches just minutes away, perfect for swimming, building sandcastles, and enjoying the sun.
  • Tangerine Farm Nature Walks: Explore scenic trails through local citrus groves where your family can enjoy a peaceful outdoor experience in the region.
  • Heritage Preservation Museum: Engage with interactive exhibits that highlight the area's history, offering an educational outing for all ages.
  • Riverfront Park Activities: Take advantage of playgrounds, picnic areas, and gentle river walks ideal for a relaxing day with your loved ones in this popular destination.
image

Adult Activities

  • Golfing at Cypress Head Golf & Country Club: Enjoy a day on the lush fairways of one of the area's premier golf courses, perfect for both beginners and seasoned players seeking scenic views and challenging play.
  • Fishing at the Halifax River: Cast your line in this popular local spot to experience relaxing freshwater or saltwater fishing with opportunities to catch a variety of species in the region.
  • Exploring Nature Trails: Discover peaceful walking and biking paths nestled within the area, ideal for outdoor enthusiasts looking to immerse themselves in the natural beauty of this destination.
  • Visiting Local Restaurants and Cafés: Savor regional flavors and fresh seafood at charming eateries nearby, offering a taste of the area's vibrant culinary scene and making for memorable dining experiences.

Other Places to Stay in Cypress Head, FL

Golf Club at Cypress Head
Golf Club at Cypress Head Vacation Rentals
More Places to Stay Near Cypress Head

Cypress Head Travel Tips

How Can You Make the Most of Your Stay?

  • Explore Local Cuisine: Savor the authentic flavors of this area by visiting local restaurants and cafes to get a true taste of the regional cuisine during your stay.
  • Plan Outdoor Activities: Make the most of the region’s pleasant weather by engaging in outdoor pursuits like walking or cycling along scenic routes nearby.
  • Discover Nearby Attractions: Use your vacation rental as a base to explore popular local spots, attractions, and natural landscapes that highlight the area's charm.
  • Utilize Concierge Services: Take advantage of personalized recommendations and services available in this destination to enhance your overall experience.

Transportation Options

  • Port Orange Taxi Services: Reliable local taxi services provide convenient transportation options around this area, making it easy to explore nearby attractions and amenities.
  • Public Bus Transportation: The regional bus system offers budget-friendly routes connecting you to key points within this destination and beyond.
  • Car Rental Agencies: Several car rental agencies in the region enable you to have flexible travel plans while enjoying your stay here.
  • Private Shuttle Services: Private shuttles are available for customized trips to popular destinations within Port Orange and surrounding communities, enhancing your overall experience.

Local Customs Options

  • Southern Hospitality: Visitors often notice the warm and friendly greeting traditions that define this area's welcoming atmosphere.
  • Cultural Festivals: The region hosts vibrant local events celebrating its diverse heritage, inviting you to experience authentic community customs.
  • Marine Conservation Practices: Respect for the nearby waterways is evident through community initiatives aimed at preserving the local aquatic environment.
  • Religious Celebrations: Traditional observances and festivities reflect the area’s rich spiritual heritage, offering insight into local customs during your stay.

Frequently Asked Questions About Cypress Head?

1. What are the top vacation rentals in Cypress Head?

There are a lot of options in Cypress Head. If you plan on staying in the Cypress Head area, consider making a reservation for a few nights at one of these properties as these have been rated the Top Vacation Rentals in Cypress Head:

2. How many vacation rentals have private pools in Cypress Head?

There are 13 vacation rentals with private pools near Cypress Head. Top-rated RBO homes that have access to a swimming pool include:

3. Which vacation homes in Cypress Head are best for families?

If you are looking for a family-friendly vacation home in Cypress Head, check out one of the following properties as all are highly-rated places to stay with excellent review for families or groups staying in Cypress Head:

4. How many Rentbyowner vacation rentals are available in Cypress Head?

Currently, the total number of properties listed by Rent By Owner in 2025 is over 82 in the Cypress Head area, and still counting. By aggregating listings from multiple websites, Rent By Owner offers an immense amount of choice of the best RBO properties in Cypress Head. 

5. What is the cancellation policy for vacation rentals in Cypress Head, Port Orange?

The cancellation policy varies by property. To find the specific details, please review the listing carefully or contact the property owner directly before booking.

6. How do I verify the safety and cleanliness standards of a vacation rental in this area?

Safety and cleanliness standards are typically outlined in the property listing. You can also reach out to the host for additional information to ensure the rental meets your expectations.

7. Are there any specific check-in and check-out procedures for vacation rentals here?

Check-in and check-out procedures are specified in each property listing. Contact the owner if you need further clarification or assistance during your arrival or departure.

8. Is Wi-Fi and other essential amenities included with vacation rentals in Port Orange?

Most listings include Wi-Fi and essential amenities; however, it’s best to confirm these details directly on the property page or by contacting the host prior to booking.

9. What should I know about local regulations or restrictions when booking vacation rentals in this region?

Local regulations regarding short-term rentals vary and may impact your stay. Review the property description for any restrictions and consult with the owner if you have concerns about compliance.

Cypress Head Top Rated Vacation Rentals

See More Cypress Head Vacation Rentals