Apartments for Rent in the Cypress Fairway Neighborhood of Orlando, FL (104 Rentals) Page 2 of 3

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property at 5152 Conroy Rd

$1,250 - $1,600

1 To 2 Bedroom Rentals

Available Now

5152 Conroy Rd

OrlandoFL32811

Orlando's Best Affordable Neighborhoods

Learn about Orlando and the best places to live with original content written by our Local Expert Darla Ferrara

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property at 5168 Conroy Rd

$1,500 - $1,650

2 Bedroom Rentals

Available Now

5168 Conroy Rd

OrlandoFL32811
property at 5124 Conroy Rd

$1,250 - $1,700

1 To 2 Bedroom Rentals

Available Now

5124 Conroy Rd

OrlandoFL32811

Neighborhood & Market Insights: How to Choose the Right Area to Rent

Master your search for the perfect apartment. Location is everything. Discover how to leverage community insights, public data, and personal visits to make a fully informed decision about where to rent.

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The Art of the Rental Viewing: What to look for during a property tour

Touring a rental? This guide helps you know exactly what to look for, from safety features to hidden flaws, so you can confidently sign your lease or keep searching.

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property at 5144 Conroy Rd

$1,690

Total Monthly Price

Total Monthly Price

Base Rent
$1,690
Total Monthly Price
$1,690

2 Bedroom, 2 Bath Condo for Rent

Available Now

5144 Conroy Rd, Unit 35

5144 Conroy Rd
OrlandoFL32811
property at 5116 Conroy Rd

$1,350

Total Monthly Price

Total Monthly Price

Base Rent
$1,350
Total Monthly Price
$1,350

1 Bedroom, 1 Bath Condo for Rent

Available Now

5116 Conroy Rd, Unit 15

5116 Conroy Rd
OrlandoFL32811
property at 5563 Millennia Park Dr

$1,500

Total Monthly Price

Total Monthly Price

Base Rent
$1,500
Total Monthly Price
$1,500

1 Bedroom, 1 Bath Condo for Rent

Available Now

5563 Millennia Park Dr, Unit 508

5563 Millennia Park Dr
OrlandoFL32811
property at 5579 Millennia Park Dr

$1,495

Total Monthly Price

Total Monthly Price

Base Rent
$1,495
Total Monthly Price
$1,495

1 Bedroom, 1 Bath Condo for Rent

Available Now

5579 Millennia Park Dr, Unit 219

5579 Millennia Park Dr
OrlandoFL32811
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Cypress Fairway
2 Bedroom Apartments

Cypress Fairway

5443 Vineland RdOrlando, FL 32811
  • Smoke Free

Smart Renter's Guide: Calculating Affordable Rent & Housing Costs

Wondering how to determine your rental budget? This comprehensive guide covers everything from the 30% rule to hidden fees and effective budgeting strategies.

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5433 Vineland Rd
1 Bedroom Apartments

5433 Vineland Rd

5433 Vineland RdOrlando, FL 32811
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Sunset Lake Condo
2 to 3 Bedroom Apartments

Sunset Lake Condo

4300-4364 S Kirkman RdOrlando, FL 32811
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Amalfi
1 to 2 Bedroom Apartments

Amalfi

4860 Cypress Woods DrOrlando, FL 32811
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Riva
Studio to 2 Bedroom Apartments

Riva

4771 Walden CirOrlando, FL 32811
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Bella Casa
1 to 2 Bedroom Apartments

Bella Casa

5501 Conroy RdOrlando, FL 32811
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Portofino
1 to 2 Bedroom Apartments

Portofino

5974 Windhover DrOrlando, FL 32819
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Studio Parc
1 Bedroom Apartments

Studio Parc

4601 S Kirkman RdOrlando, FL 32811
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The Grove at Millenia
Studio to 2 Bedroom Apartments

The Grove at Millenia

4701 Walden CirOrlando, FL 32811
  • Utilities Included
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Westbrook
1 to 3 Bedroom Apartments

Westbrook

4932 Eaglesmere DrOrlando, FL 32819
  • Utilities Included
Showing Results 51-100, Page 2 of 3

Frequently Asked Questions about Cypress Fairway

What is the current pricing and availability for apartments for rent in the Cypress Fairway area of Orlando, FL?

As of today, August 26, 2026, there are currently 104 available Cypress Fairway apartments priced from $949 to $3,355, with an average monthly rent of $1,853.

How much are Studio apartments in Cypress Fairway?

There are currently 3 Studio Apartments in Cypress Fairway with rent ranges from $949 to $1,919 with an average price of $1,312.

What is the current price range for One Bedroom Cypress Fairway Apartments for rent?

Today's rental pricing for One Bedroom Apartments in Cypress Fairway ranges from $1,115 to $2,235 with an average monthly rent of $1,476.

What does renting a Two Bedroom Apartment in Cypress Fairway cost?

The monthly rent prices of Two Bedroom Apartments currently available in Cypress Fairway range from $1,129 to $2,970. Today's average rental price for Two Bedrooms here is $1,982.

How expensive are Cypress Fairway Three Bedroom Apartments?

There are currently 19 Three Bedroom Apartments listings available in Cypress Fairway on ApartmentHomeLiving.com. The pricing ranges from $1,449 to $3,355 - averaging $2,395 for the location.

Expert Rental Resources

The rental experts at ApartmentHomeLiving.com provide you with top advice, tools, and tips for understanding the leasing process and finding the perfect rental. Here are a few helpful rental and leasing articles from our experts to guide you on your search.

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Where Orlando Locals Actually Live: A Renter's Guide to the Surrounding Cities

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Unlock Your Orlando Commute: An Expert Guide to Ideal Neighborhoods Near Major Local Employers

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Articles, How-To's, and Tips

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Practical Tips for Renters: How to Identify a Great Rental and Avoid Red Flags

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First Apartment Regrets: Real Renters Share What They'd Do Differently

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Hindsight is 20/20. Live and Learn. With age comes wisdom. We’re familiar with all those expressions, and all of them apply to lessons first-time renters learn.

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Renters Insurance 101: What It Is, What It Covers, and Why You Need It

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Insurance seems to be a part of life. In some states, having insurance is the law, as is the case for automobile insurance. Renters are no exception.

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Apartment Occupancy Rates: Renter Attraction vs Renter Retention

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There’s a tenet in marketing about client or customer attraction and retention. Studies and data have consistently shown it costs less to keep a current customer than to attract a new one.