Apartments for Rent in the Cypress Fairway Neighborhood of Orlando, FL (103 Rentals)

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The Place on Millenia
Rent Specials
$1,356 - $4,531
Total Monthly Price

Total Monthly Price

Base Rent
$1,356 - $4,531
Total Monthly Price
$1,356 - $4,531
1 to 3 Bedroom Apartments Available Now

The Place on Millenia

5215 Millenia BlvdOrlando, FL 32839
Affordability
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  • Customer Reviewed
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The Fitzgerald
$1,327 - $2,090
Total Monthly Price

Total Monthly Price

Base Rent
$1,327 - $2,090
Total Monthly Price
$1,327 - $2,090
1 to 3 Bedroom Apartments Available Now

The Fitzgerald

4581 S Kirkman RdOrlando, FL 32811
Affordability
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  • Utilities Included

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

Why fight Orlando's tourist traffic when you don't have to? Explore the best cities surrounding Orlando for renters, with expert tips on commuting, lifestyle, hidden costs, and where to find the most value.

Read Article
property at 5429 Vineland Rd

$1,950

Total Monthly Price

Total Monthly Price

Base Rent
$1,950
Total Monthly Price
$1,950

2 Bedroom, 2 Bath Condo for Rent

Available Now

5429 Vineland Rd, Unit 00

5429 Vineland Rd
OrlandoFL32811
property at 5415 Vineland Rd

$3,000

Total Monthly Price

Total Monthly Price

Base Rent
$3,000
Total Monthly Price
$3,000

2 Bedroom, 2.5 Bath Townhome for Rent

Available Now

5415 Vineland Rd

OrlandoFL32811

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

From theft to fire to water damage, the unexpected can happen to any renter. Discover why renters insurance is one of the smartest and most affordable investments you can make as a tenant.

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property at 4740 Walden Cir

$1,050

Total Monthly Price

Total Monthly Price

Base Rent
$1,050
Total Monthly Price
$1,050

1 Bedroom, 1 Bath Condo for Rent

Available Now

4740 Walden Cir, Unit Walden

4740 Walden Cir
OrlandoFL32811
property at 5120 Conroy Rd

$1,650

Total Monthly Price

Total Monthly Price

Base Rent
$1,650
Total Monthly Price
$1,650

2 Bedroom, 2 Bath Condo for Rent

Available Now

5120 Conroy Rd, Unit 27

5120 Conroy Rd
OrlandoFL32811
property at 4711 Capri Plz

$1,600

Total Monthly Price

Total Monthly Price

Base Rent
$1,600
Total Monthly Price
$1,600

2 Bedroom, 2 Bath Condo for Rent

Available Now

4711 Capri Plz, Unit 188

4711 Capri Plz
OrlandoFL32811

The Soul of the City Beautiful: What Life in Orlando Is Really Like

Orlando is much more than theme parks. Uncover the city's rich history, diverse neighborhoods like Winter Park and Downtown, and its bustling cultural and culinary life.

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property at 5467 Vineland Rd

$1,380 - $1,750

1 To 2 Bedroom Rentals

Available Now

5467 Vineland Rd

OrlandoFL32811

Top Neighborhoods Near Orlando Major Employers

Learn about the best places to live near major employers in Orlando with original content written by our Local Expert Darla Ferrara

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property at 5483 Vineland Rd

$1,750 - $2,300

2 To 3 Bedroom Rentals

Available Now

5483 Vineland Rd

OrlandoFL32811

How I Find the Perfect Rental for My Clients: A Real Estate Pro's Guide

Finding the right apartment starts with three things: location, cost, and amenities. Get the insider perspective from a real estate professional on how to nail all three.

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Showing Results 1-50, Page 1 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 103 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.

Helpful Local Expert Guides

decorative image for Where Orlando Locals Actually Live: A Renter's Guide to the Surrounding Cities article

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

Written by: Darla Ferrara

When people think of Orlando, FL, the iconic theme parks and buzz of downtown tend to steal the spotlight.

decorative image for The Soul of the City Beautiful: What Life in Orlando Is Really Like article

The Soul of the City Beautiful: What Life in Orlando Is Really Like

Written by: Darla Ferrara

When people think of Orlando, Florida, they dream of theme parks and sunny weather, and rightfully so. It’s that energy that keeps this city a mainstay in the global tourist industry.

decorative image for Unlock Your Orlando Commute: An Expert Guide to Ideal Neighborhoods Near Major Local Employers article

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

Written by: Darla Ferrara

When I first moved to Orlando, Florida, in the 1990s, one of the things that drew me here was the remarkably low unemployment rates. There was a job for everyone. Two decades later, that fundamental appeal remains.

decorative image for Your Guide to the Perfect Orlando Neighborhood for Student Renters article

Your Guide to the Perfect Orlando Neighborhood for Student Renters

Written by: Darla Ferrara

There is never a dull moment in Orlando, Florida. Along with top-tier universities, technical schools, and local colleges, there are world-class entertainment venues, the ocean within driving distance, and lots of sunshine.

Articles, How-To's, and Tips

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

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

Written by: Robin Stewart

Renters want to find a great apartment, the right place for them, one that checks all the boxes of location, rental cost, amenities, safety, and more.

decorative image for First Apartment Regrets: Real Renters Share What They'd Do Differently article

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

Written by: Robin Stewart

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.

decorative image for Renters Insurance 101: What It Is, What It Covers, and Why You Need It article

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

Written by: Robin Stewart

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.

decorative image for Apartment Occupancy Rates: Renter Attraction vs Renter Retention article

Apartment Occupancy Rates: Renter Attraction vs Renter Retention

Written by: Robin Stewart

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.