Discover Your Perfect Cypress Island Vacation Homes

Best Vacation Homes in Cypress Island

See More Cypress Island Vacation Rentals

Cypress Island Luxury Rentals

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

Cypress Island Pet Friendly Vacation Rentals

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

Cypress Island Large Vacation Homes

See More Family Vacation Rentals in Cypress Island on FVR

Why Choose Rent By Owner for your Cypress Island 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.

Best Times to Visit Cypress Island

When should you plan your Vacation Rentals stay?

Finding the ideal time to visit this destination ensures you can enjoy its best weather and activities, making your stay in Cypress Island memorable and relaxing.

Peak Season Highlights

winter
Winter (December to February)

During the winter months, you can enjoy pleasant weather with less rainfall, making it an ideal time for outdoor activities and exploring the area.

Average Temperature Daytime: 75°F - Nighttime: 55°F
spring
Spring (March to May)

Spring offers warm temperatures and blooming scenery, creating a lively atmosphere that enhances your stay in this destination.

Average Temperature Daytime: 82°F - Nighttime: 60°F

Off-Season Highlights

image
Summer (June to August)

Summer can be hot and humid, but it’s a quieter time to find more affordable vacation rentals and enjoy the region without the crowds.

Average Temperature Daytime: 88°F - Nighttime: 72°F
image
Fall (September to November)

Autumn features milder weather and fewer visitors, perfect for relaxing and discovering this destination at a more leisurely pace.

Average Temperature Daytime: 83°F - Nighttime: 62°F

Weekly Weather Forecast for Cypress Island

How to Book Your Cypress Island 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 Island

More Top-Rated Vacation Rentals in Cypress Island 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 private outdoor spaces, perfect for relaxing under the sun or having a quiet evening.
  • Take advantage of outdoor dining areas, ideal for savoring meals while experiencing the warm Florida breeze.
  • Make use of community swimming pools to cool off and unwind during your stay here.
  • Benefit from well-maintained walking trails or landscaped gardens that showcase the area's natural beauty.
  • Utilize outdoor grilling stations for hosting barbecues amidst the scenic surroundings.
  • Relax on spacious patios or verandas with comfortable seating, offering great views of the region.
  • Spend time on the nearby lakes or ponds, with some rentals providing direct access for fishing or kayaking.

Top Attractions Around Cypress Island

What attractions are nearby?

Within the area, you can enjoy a variety of outdoor activities such as boating, fishing, and exploring scenic parks that showcase the natural beauty of this destination in Bonita Springs.

image
image

Family Activities

  • Estero Bay Preserve State Park: Explore the scenic trails and observe local wildlife along the protected waters right in the region.
  • Fishing Charters in the Area: Enjoy a family-friendly fishing adventure on the calm waters nearby, known for its abundant marine life.
  • Family Beach Days: Relax and play on the pristine sands of nearby beaches, perfect for building sandcastles and swimming with the kids.
  • Nature Center Visits: Engage your family with educational exhibits and guided nature walks that highlight the area's unique ecosystem.
image

Adult Activities

  • Kayaking and Paddleboarding: Explore the calm waters around Cypress Island by renting a kayak or paddleboard, offering a peaceful way to enjoy the natural beauty of Bonita Springs.
  • Fishing Excursions: Engage in guided fishing trips within this region's abundant waters, perfect for adults looking to unwind and connect with nature.
  • Golfing at Premier Courses: Play a round on nearby golf courses renowned for their lush landscapes and challenging fairways, ideal for sport enthusiasts staying here.
  • Sunset Dolphin Cruises: Experience breathtaking sunsets while onboard a dolphin cruise that showcases the area's vibrant marine life along this coastal destination.

Cypress Island Travel Tips

How Can You Make the Most of Your Stay?

  • Explore Local Nature Trails: Take advantage of the scenic paths nearby to immerse yourself in the area's natural beauty and enjoy peaceful outdoor experiences during your stay.
  • Visit Nearby Beaches: Make time to relax on the pristine shores that offer stunning views and a perfect setting for sunbathing or beachside strolls.
  • Discover Waterfront Dining: Savor fresh local cuisine at restaurants close to your rental, providing an authentic taste of the region's culinary delights.
  • Plan Water-Based Activities: Engage in kayaking, paddleboarding, or fishing in the surrounding waters to fully experience the area's aquatic offerings.

Transportation Options

  • Personal Vehicles: Renting a car provides the flexibility to explore Bonita Springs and its surroundings at your own pace when staying in Cypress Island.
  • Taxis and Rideshare Services: Taxis and rideshare options like Uber or Lyft offer convenient, on-demand transportation around the area without the need for personal vehicle ownership.
  • Public Transit: Local bus services operate within the region, offering an affordable way to reach nearby attractions from your vacation rental here.
  • Bicycle Rentals: Cycling is a popular way to enjoy the scenic views of the area, with bike rentals readily available for exploring the region's picturesque surroundings.

Local Customs Options

  • Southern Hospitality: Locals here are known for their warm and welcoming attitude, making you feel at home during your stay in this area.
  • Respect for Nature: It is customary to show reverence for the region’s natural environment, especially when engaging in outdoor activities near the water or nature preserves.
  • Casual Dress Code: Visitors are often encouraged to dress comfortably and casually, reflecting the relaxed lifestyle prevalent in this destination.
  • Local Dining Etiquette: When enjoying meals at nearby eateries, it’s appreciated to acknowledge regional flavors and partake respectfully in communal dining traditions.

Frequently Asked Questions About Cypress Island?

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

There are a lot of options in Cypress Island. If you plan on staying in the Cypress Island 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 Island:

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

There are 147 vacation rentals with private pools near Cypress Island. Top-rated RBO homes that have access to a swimming pool include:

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

If you are looking for a family-friendly vacation home in Cypress Island, 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 Island:

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

Currently, the total number of properties listed by Rent By Owner in 2025 is over 826 in the Cypress Island 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 Island. 

Cypress Island Top Rated Vacation Rentals

10.0 (40 Reviews)
House
Old Florida Canal Home
  • Air Conditioner
  • Parking
  • Pet Friendly
View Availability
See More Cypress Island Vacation Rentals