2 Bedroom Apartments for Rent in Oakland, FL (40 Rentals)

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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.

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

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Park Avenue Villas
2 Bedroom Apartments

Park Avenue Villas

48 S Park AveWinter Garden, FL 34787
  • Utilities Included
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West Pointe Villas
2 Bedroom Apartments

West Pointe Villas

1201 W Pointe Villas BlvdWinter Garden, FL 34787
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Palm Crossing
2 Bedroom Apartments

Palm Crossing

1240 Winter Garden Vineland RdWinter Garden, FL 34787

Orlando's Best Affordable Neighborhoods

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

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410 S Park Ave
2 Bedroom Apartments

410 S Park Ave

410 S Park AveWinter Garden, FL 34787
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Oakland, FL Local Guide

Largest Available Oakland 2 Bedroom Apartments

The largest available 2 Bedroom apartment unit in Oakland, FL is found at The Lodge at Hamlin in the Southbridge Village Townhomes neighborhood and is 1,616 square feet priced from $3,192. The Alibi at Lake Lilly in the Ashton Park neighborhood has the second largest 2 Bedroom, which is sized at 1,575 square feet and currently listed start at $3,070. Here is today’s list of the largest available 2 Bedroom units in Oakland:

Apartment ListingModel NameSquare FootagePriced From
The Lodge at HamlinB51,616 Sq Ft$3,192
The Alibi at Lake LillyEllington B6T1,575 Sq Ft$3,070
The Haven at Lake BrittSanctuary D1 Two-Car Townhome1,553 Sq Ft$3,310
Casa Mirella Apartments2x2 - 2c2 - 1408 sqft1,408 Sq Ft$1,863
Vista at Lost LakeB91,406 Sq Ft$1,931
Windermere at Lakes Edge ApartmentsDuval Key1,397 Sq Ft$1,997
The Vineyards at Hammock RidgeStover1,360 Sq Ft$1,964
Lakewalk at HamlinFischer1,330 Sq Ft$3,315
Addison At WindermereThe Casper1,299 Sq Ft$2,105
AVENUE ON OAKLANDB2 (Sycamore)1,291 Sq Ft$1,984

Cheapest Available Oakland 2 Bedroom Apartments

As of June 29, 2025 the lowest priced 2 Bedroom apartment unit in Oakland, FL is the Cypress Renovated Model starting from $1,544 at Advenir at The Oaks in the Ashton Park neighborhood. The second most affordable Oakland 2 Bedroom is the Two Bed/1.5 Bath Upgraded Model at Garden City Apartments starting at $1,600 in the Courtlea Park neighborhood. The average price for all 2 Bedroom apartments in Oakland is currently $2,270. Here is today’s list of the cheapest available 2 Bedroom options in Oakland:

Apartment ListingModel NamePriced From
Advenir at The OaksCypress Renovated$1,544
Garden City ApartmentsTwo Bed/1.5 Bath Upgraded$1,600
Inland Seas ApartmentsTwo Bed/ Two Bath$1,640
Palm CrossingValencia$1,714
Advenir at ClermontPomelo$1,714
Windermere at Lakes Edge ApartmentsCoral Key$1,737
Citrus TowerB1$1,745
Vista at Lost LakeB1$1,749
Arya at WindermereSapphire$1,776
Sundance at ClermontSierra Orchid$1,793

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.

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Pet Friendly Lifestyle
Oakland, FL

Ranked #187

Among cities in Florida for Apartment listings with Pet Friendly Amenities

Pet Friendliness Lifestyle Score

2.5
Pet Friendly

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Remember the 3 Rules of Real Estate:
Location, Location, Location!

Explore Oakland, FL Rentals by Map

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See the most popular apartments and homes in Oakland, FL

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Getting Around Oakland, FL

Walk Score®

20 / 100

Car-Dependent

Almost all errands require a car

Bike Score®

43 / 100

Somewhat Bikeable

Minimal bike infrastructure

Transit Score®

2 / 100

Minimal Transit

It may be possible to get on a bus

What Are Walk Score®, Transit Score®, and Bike Score® Ratings?

  • Walk Score® measures the walkability of any address.
  • Transit Score® measures access to public transit.
  • Bike Score® measures the bikeability of any address.

Frequently Asked Questions about 2 Bedroom Oakland Apartments

What is the Cheapest apartment in Oakland with 2 Bedroom?

Currently the most affordable 2 Bedroom in Oakland is at Advenir at The Oaks listed at $1,544.

How much is the average rent for a 2 Bedroom Oakland Apartment?

The average rent for a 2 Bedroom Apartment in Oakland is $2,270.

What is the largest available 2 Bedroom Oakland Apartment for rent?

Today's apartment with the most square footage in Oakland is a 1,616 square feet unit starting from $3,192 at The Lodge at Hamlin.

What is the average size for Oakland 2 Bedroom Apartments for rent?

The average size for a 2 Bedroom rental in Oakland is currently 1,273 sq ft.

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.

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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.

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Roommate Matching: Finding the Right Fit and Avoiding Pitfalls

Written by: Cheryl Bowman

A fantastic way to save money and enjoy a built-in community is to share an apartment. However, a bad roommate situation can turn your dream rental into a nightmare.

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

Written by: Marie Brown

You’ve scrolled through countless listings, walked through a blur of rentals, and finally found what feels like the one. The pictures? Fantastic. The neighborhood seems just right.

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Know Your Budget: Calculating What You Can Realistically Afford When Renting

Written by: Lauren Harrington

Renting an apartment or house isn’t just about looking through online ads, choosing a few apartments or homes you want to tour, filling out an application, and putting down a deposit. Those things are all necessary and important.