Cheap Homes for Rent in Cypress Fairway Neighborhood of Orlando, FL from $900 (23 Rentals)

How Many Bedrooms?Done
Select your price rangeDone
By AmenitiesDone
By Community TypeDone
Features and AvailabilityDone
Done

Search the lowest-cost Homes available for rent right now in the Cypress Fairway area of Orlando.

property at 5140 Conroy Rd

5140 Conroy Rd

OrlandoFL32811

Don't Settle: How to Negotiate Your Apartment Lease and Save Money

Discover the insider tips from an attorney and real estate agent on how to negotiate your next apartment lease. Find out what's on the table and what's not, so you can save money and get the best terms possible.

Read Article
property at 5160 Conroy Rd

5160 Conroy Rd

OrlandoFL32811
property at 5483 Vineland Rd

5483 Vineland Rd

OrlandoFL32811
property at 5120 Conroy Rd

5120 Conroy Rd

OrlandoFL32811

Your Guide to Co-Signers: The Risks, Rewards, and Everything in Between

Thinking about getting a co-signer for your rental application? We break down what a co-signer is, the potential benefits, and the serious risks for both parties. Find out if it's the right choice for you.

Read Article
property at 5152 Conroy Rd

5152 Conroy Rd

OrlandoFL32811

Roommate Matching: Finding the Right Fit and Avoiding Pitfalls

When searching for a roommate, follow this list of essential steps and set clear expectations to create a solid foundation for a harmonious living situation.

Read Article
Showing Results 1-23, Page 1 of 1

Cypress Fairway, Orlando, FL Local Guide

Cheapest Available Cypress Fairway Apartments for Rent

 

The cheapest available apartment rental in the Cypress Fairway area of Orlando, FL is a 1 Bed unit found at West Winds Apartments priced from $1,215. Walden Palms has the second lowest priced unit, which is a 1 Bed apartment currently listed from $1,250. Here are the most affordable Cypress Fairway apartments for rent in Orlando, FL:

Apartment ListingModel NameBed/BathPriced From
West Winds ApartmentsCity Breeze1BR,1BA$1,215
Walden PalmsA1-1 Bedroom, 1 Bathroom1BR,1BA$1,250
Twelve Oaks at WindermereA1 | Standard1BR,1BA$1,290
Fountains at Millenia ApartmentsThree Bedroom Two Bath (c)3BR,2BA$1,299
Coconut PalmsAvalon1BR,1BA$1,299

Best Value Apartments for Rent in Cypress Fairway, FL

As of October 15, 2025 the best value apartment in the Cypress Fairway area is the $1.63 price per square foot Three Bedroom Two Bath Model at Fountains at Millenia Apartments in the in the Millenia neighborhood starting from $1,979. The second greatest value Cypress Fairway apartment is the Dorado Model at Bella Vita starting at $1,549 with a $1.45 price per square foot in the Millenia neighborhood. Here is today’s list of the best values for Cypress Fairway apartments based on price per square foot:

Apartment ListingModel NameBed/BathPrice Per Sq.Ft.
Fountains at Millenia ApartmentsThree Bedroom Two Bath3BR,2BA$1.63
Bella VitaDorado3BR,2BA$1.45
The FitzgeraldB12BR,1BA$1.89
Aria at Millenia ApartmentsA21BR,1BA$2.06
The Villages on Millenia ApartmentsOne Bedroom One Bath1BR,1BA$1.79
The Place on MilleniaSolano1BR,1BA$2.08
Regatta at UniversalA1B1BR,1BA$2.04
PalioOnda1BR,1BA$1.92
Century MilleniaThe Athens1BR,1BA$2.04
Millenium CoveA11BR,1BA$2.17

Quick Rent Budget Calculator

How much rent can you afford?

The common "Rule of Thumb" is that rent should be no more than 30% of your income. How much is that? Enter your monthly income and click "Calculate My Budget" to find out.

decorative image of people with a giant lease agreement

Pet Friendly Lifestyle
Cypress Fairway, Orlando, FL

Ranked #254

Among cities in Florida for Apartment listings with Pet Friendly Amenities.

Pet Friendliness Lifestyle Score

2.5
Pet Friendly

decorative image of woman handing cat to small boy

Frequently Asked Questions about Cypress Fairway

What type of rentals are currently available in Cypress Fairway?

There are currently 36 Apartments for Rent in Cypress Fairway, FL with pricing that ranges from $1,020 to $3,820. There are also 79 Single Family Homes for rent, Condos, and Townhome rentals currently available in Cypress Fairway ranging from $900 to $4,400.

What is the current price range for Rental Homes in Cypress Fairway?

Today's rental pricing for Homes for Rent, Condos and Townhomes in Cypress Fairway ranges from $900 to $4,400 with an average monthly rent of $2,450.

How much are larger Three and Four Bedroom Rentals in Cypress Fairway?

For those who are looking for larger living arrangements, Three Bedroom Apartments in Cypress Fairway range from $1,299 to $3,820, while Three Bedroom Homes, Condos, and Townhomes for rent range from $1,595 to $3,200. Four Bedroom Single-Family rentals are also available starting from $4,400 and Four Bedroom Apartments start at $1,899.

Expert Rental Resources

Helpful Apartment Articles, How-To's and Tips

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.

decorative image for An Orlando Local Expert’s Guide To 10 Budget-Friendly Neighborhoods to Rent article

An Orlando Local Expert’s Guide To 10 Budget-Friendly Neighborhoods to Rent

Written by: Darla Ferrara

For many, Orlando is the place where you vacation, not live. However, this city, located in the central region of Florida, offers a vibrant tech community, plenty of outdoor activities, and some of the best schools in the country.

decorative image for How to Negotiate Your Apartment Lease and Save Money article

How to Negotiate Your Apartment Lease and Save Money

Written by: Christine Leonard, Esq.

Everything is a negotiation in real estate! 

decorative image for The Rental Move-In Inspection Checklist: A Guide for Renters article

The Rental Move-In Inspection Checklist: A Guide for Renters

Written by: Trey Huguley

The move-in inspection checklist is a crucial tool for both tenants and landlords. This checklist, provided by the team at ApartmentHomeLiving.com, helps document the condition of an apartment at the time of move-in.

decorative image for Your Guide to Co-Signers: The Risks, Rewards, and Everything in Between article

Your Guide to Co-Signers: The Risks, Rewards, and Everything in Between

Written by: Christine Leonard, Esq.

For many people, obstacles can arise during the rental application process for a variety of issues.