5451 Vineland Rd
OrlandoFL32811
Cheap Homes for Rent in Cypress Fairway Neighborhood of Orlando, FL from $1,200 (24 Rentals)
Search the lowest-cost Homes available for rent right now in the Cypress Fairway area of Orlando.
4724 Walden Cir
OrlandoFL32811
4772 Walden Cir
OrlandoFL32811
5128 Conroy Rd
OrlandoFL32811
4736 Walden Cir
OrlandoFL32811
5152 Conroy Rd
OrlandoFL32811
5120 Conroy Rd
OrlandoFL32811
5459 Vineland 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.
4356 S Kirkman Rd
OrlandoFL32811
5471 Vineland Rd
OrlandoFL32811
5160 Conroy Rd
OrlandoFL32811
5129 Eaglesmere Dr
OrlandoFL32819
5164 Conroy Rd
OrlandoFL32811
4716 Walden Cir
OrlandoFL32811
5447 Vineland Rd
OrlandoFL32811
4312 S Kirkman 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.
4744 Walden Cir
OrlandoFL32811
4720 Walden Cir
OrlandoFL32811
5455 Vineland Rd
OrlandoFL32811
4760 Walden Cir
OrlandoFL32811
5156 Conroy Rd
OrlandoFL32811
5409 Pine Creek Dr
OrlandoFL32811
5323 Indian Creek Dr
OrlandoFL32811
5483 Vineland Rd
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.
Showing Results 1-24, Page 1 of 1
Cypress Fairway, Orlando, FL Local Guide
How much does it cost to rent a home in Cypress Fairway?
| Bedroom | Average Rent | Cheapest Rent | Highest Rent |
|---|---|---|---|
| Cypress Fairway 2 Bedroom Homes for Rent | $1,957 | $1,395 | $3,200 |
| Cypress Fairway 3 Bedroom Homes for Rent | $2,158 | $1,750 | $2,950 |
| Cypress Fairway 4 Bedroom Homes for Rent | $3,336 | $3,049 | $3,995 |
Browse Homes for Rent in this Neighborhood
There are currently 24 rentals with your search options within a 1 mile radius of the Cypress Fairway Neighborhood of Orlando, FL.
Explore Orlando
Let everyone know!
Do you know the Cypress Fairway area?
If you’re an expert on all things Cypress Fairway, tell us what you love (and don't) by rating it and writing a review.
Write a Review
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 The Villages on Millenia Apartments priced from $1,068. Riva has the second lowest priced unit, which is a Studio apartment currently listed from $1,099. Here are the most affordable Cypress Fairway apartments for rent in Orlando, FL:
| Apartment Listing | Model Name | Bed/Bath | Priced From |
|---|---|---|---|
| The Villages on Millenia Apartments | One Bedroom One Bath | 1BR,1BA | $1,068 |
| Riva | Catamaran | Studio,1BA | $1,099 |
| Coconut Palms | Estereo Bay | Studio,1BA | $1,099 |
| West Winds Apartments | City Breeze | 1BR,1BA | $1,215 |
| Walden Palms | A1-1 Bedroom, 1 Bathroom | 1BR,1BA | $1,250 |
Best Value Apartments for Rent in Cypress Fairway, FL
As of February 02, 2026 the best value apartment in the Cypress Fairway area is the $1.51 price per square foot Tartuca Model at Palio in the in the Millenia neighborhood starting from $1,899. The second greatest value Cypress Fairway apartment is the Three Bedroom Two Bath (b) Model at Fountains at Millenia Apartments starting at $1,299 with a $1.07 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 Listing | Model Name | Bed/Bath | Price Per Sq.Ft. |
|---|---|---|---|
| Palio | Tartuca | 3BR,2BA | $1.51 |
| Fountains at Millenia Apartments | Three Bedroom Two Bath (b) | 3BR,2BA | $1.07 |
| Bella Capri | Monte Capello | 3BR,2BA | $1.63 |
| Amalfi | Captiva | 2BR,2BA | $1.64 |
| Positano | The Moscato | 2BR,2BA | $1.69 |
| Bella Casa | Millenia | 2BR,1.5BA | $1.56 |
| The Fitzgerald | B1 | 2BR,1BA | $1.75 |
| The Grove at Millenia | B1 Standard | 2BR,1BA | $1.74 |
| The Villages on Millenia Apartments | One Bedroom One Bath | 1BR,1BA | $1.31 |
| Bella Vita | Castillo | 1BR,1BA | $1.90 |
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 $1,068 to $3,820. There are also 78 Single Family Homes for rent, Condos, and Townhome rentals currently available in Cypress Fairway ranging from $1,245 to $3,995.
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 $1,245 to $3,995 with an average monthly rent of $2,209.
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 $1,750 to $2,950. Four Bedroom Single-Family rentals are also available starting from $3,049 and Four Bedroom Apartments start at $1,665.
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
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.
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.
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.
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.
Articles, How-To's, and Tips
18 Must-Ask Rental Tour Questions That Reveal the Truth about a Property
Written by: Lauren Harrington
Renting your next home can feel thrilling and overwhelming at the same time.
A Renters Guide for Tips on Writing Your Notice for Not Renewing Your Apartment
Written by: Bob Mallory
Packing up everything you own to move is so stressful for many that ending your apartment lease can feel like a small or unimportant task. Ending your lease involves more than simply turning over your keys on the last day.
Renting with Roommates: Realistic Expectations for Shared Lease
Written by: Christine Leonard, Esq.
Given the high costs for housing, I have found that many people are looking for a roommate to share expenses. These arrangements can increase opportunities for more desirable and larger spaces.
Apartment Common Area Rules: What Renters Need to Know
Written by: Christine Leonard, Esq.
Back in the day when I rented one of my first apartments, the property didn’t even have laundry in the building. Now, rental properties are often competing against each other to provide the best amenities.