2 Bedroom Apartments for Rent in Oakland, FL (47 Rentals)

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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.

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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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The Ultimate Long-Distance Moving Checklist: Tips from a Real Estate Pro

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Discover how your credit score impacts your ability to lease or buy a home. Learn how credit scores are determined, how to check yours, and strategies to improve it for real estate success.

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Park Avenue Villas
2 Bedroom Apartments

Park Avenue Villas

48 S Park AveWinter Garden, FL 34787
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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

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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50 W Story Rd
2 Bedroom Apartments

50 W Story Rd

50 W Story RdWinter Garden, FL 34787
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166 W Morgan St
2 Bedroom Apartments

166 W Morgan St

166 W Morgan StWinter Garden, FL 34787
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410 S Park Ave
2 Bedroom Apartments

410 S Park Ave

410 S Park AveWinter Garden, FL 34787
Showing Results 1-47, Page 1 of 1

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 $3,280. 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$3,280
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 MirellaB21,408 Sq Ft$1,941
Vista at Lost LakeB91,406 Sq Ft$1,983
Addison At WindermereThe Kaiden1,398 Sq Ft$2,370
Windermere at Lakes Edge ApartmentsDuval Key1,397 Sq Ft$1,986
AVENUE ON OAKLANDB2 (Sycamore)1,291 Sq Ft$2,072
Skyline at Westfall StationB51,261 Sq Ft$1,890
Homestead at HamlinLineage1,251 Sq Ft$2,397

Cheapest Available Oakland 2 Bedroom Apartments

As of September 19, 2025 the lowest priced 2 Bedroom apartment unit in Oakland, FL is the Pomelo Model starting from $1,529 at Advenir at Clermont in the Lincoln Park neighborhood. The second most affordable Oakland 2 Bedroom is the Cypress Renovated Model at Advenir at The Oaks starting at $1,529 in the Ashton Park neighborhood. The average price for all 2 Bedroom apartments in Oakland is currently $2,242. Here is today’s list of the cheapest available 2 Bedroom options in Oakland:

Apartment ListingModel NamePriced From
Advenir at ClermontPomelo$1,529
Advenir at The OaksCypress Renovated$1,529
Palm CrossingValencia$1,599
Inland Seas ApartmentsTwo Bed/ Two Bath$1,640
Garden City ApartmentsTwo Bed/1.5 Bath Standard$1,650
Sundance at ClermontSierra Orchid$1,726
WinterwoodsTwo Bedroom Two Bath with Master Bedroom Apartment$1,750
Park Place at Maguire ApartmentsB1$1,773
Arya at Windermere 55+ Active Adult LivingSapphire$1,776
Citrus TowerB1$1,816

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Pet Friendly Lifestyle
Oakland, FL

Ranked #323

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 Clermont listed at $1,529.

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

The average rent for a 2 Bedroom Apartment in Oakland is $2,242.

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 $3,280 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 1,232 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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How to Negotiate Your Apartment Lease and Save Money

Written by: Christine Leonard, Esq.

Everything is a negotiation in real estate! 

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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.

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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.