Location: Oldsmar
Do Not Show Listings
111 E CYPRESS CT #111, OLDSMAR, FL 34677
$1,90088 Days on yellowkey MLS ID: TB8499374
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1054 Built: 1980Community: East Lake Woodlands Cypress EstatesCondo
Market Analysis: For SaleFor RentSoldRented
Nearby Properties: For SaleFor RentSoldRented
Taxes:
Elementary School: None
High School: None
Tax Year:
Middle School: None
Remarks: Off Season Condo Available May 1st through December 30th. Cypress Estates of East Lake Woodlands Country Club Community This two-bedroom, two-bathroom condo on the first floor has eat-in kitchen, screen enclosed patio and split bedroom plan. Livingroom/dining room combination with leather furniture, dining table close to open kitchen and enclosed patio where washer and dryer are located in closet. Queen bed in primary and bedroom shower in primary bathroom. Twin beds in quest bedroom with tub in guest bathroom. Rent includes water, sewer, trash, basic cable, local phone service and up to $100 per month of electric. Rates are subject to 13% sales/tourist tax. Please call for availability.
Listing is courtesy of: PREFERRED REALTY GROUP, LLC (727-418-1020)
Listing Agent: Sandy Harris (727-365-3930)
107 WINDWARD PL #107, OLDSMAR, FL 34677
$2,00060 Days on yellowkey MLS ID: TB8508465
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 879 Built: 1984Community: Meadows Condo At East Lake WoodlandsCondo
Elementary School: Cypress Woods Elementary-PN
High School: East Lake High-PN
Middle School: Carwise Middle-PN
Remarks: Available June 1 though October 31. Rest and relaxation are the 'key' to this beautifully decorated first floor condo in The Meadows of gated East Lake Woodlands Country Club community. Tile flooring thru out the living area with comfortable setting to watch your flat screen tv or out to the glass enclosed lanai to enjoy your new book! Dining area to set up a more formal table or grab a bite in the eat in kitchen area. Kitchen has stainless appliances, breakfast bar overlooking the dining/living area. Split bedroom plan. Primary bedroom with queen size bed, tv, walk in closet and sliders out to the lanai (where the washer and dryer are located in the utility closet). Primary ensuite bath with tiled walk in shower and linen closet. Guest bedroom with twin beds, tv and guest bath with tub/shower combination. This is a non-smoking/vaping residence, and all short term rentals are subject to a 13% sales/tourist tax. Water, sewer, trash, basic cable, internet and up to $100 in electric included in the rent. Please call for availability.
270 WOODLAKE WYNDE #270, OLDSMAR, FL 34677
$1,625151 Days on yellowkey MLS ID: TB8476906
0 Days Off yellowkey (back on 6/9/2026)
Bed: 1 Bath: 1.0 Liv Area Sq Ft: 674 Built: 1985Community: East Lake Woodlands Woodlake RunCondo
Remarks: AVAILABLE MARCH 1st - FULLY FURNISHED, second floor condo with vaulted ceilings in the Woodlake Run area of gated East Lake Woodlands Country Club community. Private foyer tiled entrance takes you to the dining/living area with vaulted ceilings and clear view windows to keep it light and bright. Efficient kitchen with window has built in microwave, wall pantry and pass thru window into the living area. Sliders from the living area and the bedroom out to the screen enclosed wrap around lanai has storage closet, ceiling fan, and utility closet where the washer and dryer are located. Bedroom with king size bed, ceiling fan, walk in closet and large linen closet. Bathroom offers large vanity area and shower/tub combination. Flat screen tv's in living area and bedroom. The community offers two heated pools and private membership to the golfing Country Club. This is a nonsmoking/vaping residence with water, sewer, trash, basic cable and internet included in the rent. No pets please.
112 CYPRESS CT #112, OLDSMAR, FL 34677
$1,75051 Days on yellowkey MLS ID: TB8506877
REDUCED by $50 (2.8%) on 05/30/2026
Remarks: Located at 112 Cypress Ln, Oldsmar, FL 34677, this charming 2-bedroom, 2-bath condo in the desirable East Lake Woodlands / Cypress Estates community offers comfortable, Florida living in a peaceful, gated setting with community pool access and well-maintained grounds. The home features a split floor plan, in-unit laundry, and a private screened patio — perfect for morning coffee or relaxing evenings. Residents enjoy the convenience of a secure neighborhood while being just minutes from shopping, dining, entertainment, and major roadways connecting you to Clearwater, Tampa, St. Petersburg, and beautiful Gulf Coast beaches. Oldsmar itself is a vibrant Pinellas County city with great schools, parks, and community events, providing both convenience and lifestyle appeal for full-time residents or seasonal guests alike. Move in requires first month, last month and $2000 deposit. Total amount required to move in for qualified tenants is $5500. No Application Fees! Drive by and Call us for Approval!
Listing is courtesy of: EXP REALTY LLC (888-883-8509)
Listing Agent: Wil Sanders (813-380-6048)
47 EMERALD BAY DR, OLDSMAR, FL 34677
$1,75077 Days on yellowkey MLS ID: TB8492525
REDUCED by $50 (2.8%) on 05/26/2026
Bed: 2 Bath: 1.5 Liv Area Sq Ft: 1100 Built: 1990Community: Emerald BayTownhouse
Remarks: Emerald Bay Townhome in Oldsmar just off Tampa Road. Great room floor plan on the first floor with sliders out to screen enclosed lanai off living area. Kitchen with pantry and breakfast bar overlooking the living area and separate dining nook. Two bedrooms and bathroom on second floor along with washer and dryer in utility closet. Large outside storage closet, covered parking and community pool nearby. Rent includes trash and lawn service. All Century21 Integra residents are enrolled in the Resident Benefits Package (RBP) for $50.00/month which includes liability insurance, credit building to help boost the resident’s credit score with timely rent payments, up to $1M Identity Theft Protection, HVAC air filter delivery (for applicable properties), move-in concierge service making utility connection and home service setup a breeze during your move-in, our best-in-class resident rewards program, and much more! More details upon application.
Listing is courtesy of: CENTURY 21 INTEGRA (800-593-7653)
Listing Agent: Becki Server (727-835-9696)
161 LAKESIDE DR, OLDSMAR, FL 34677
$2,00056 Days on yellowkey MLS ID: TB8511614
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1094 Built: 1981Community: East Lake Woodlands CondoSpa: NoCondo
Elementary School: Forest Lakes Elementary-PN
Remarks: Call Fonda Dillard 813-514-5222 to Discover your perfect getaway! This inviting, fully furnished 2-bedroom, 2-bath condo awaits your arrival. Simply bring your essentials to enjoy a comfortable, updated living space, complete with in-unit washer and dryer. 2 bedrooms and they are seperated by closet space and bathrooms for privacy. Embrace tranquility on the back patio, offering serene lake views and glimpses of local wildlife. Located in a golf community for that well maintained and clean looks, you're moments away from shopping, dining, and entertainment. Available for a 3-month minimum stay from June 1 to October 31. Please note, pets are not permitted. Make this your home away from home; call now to secure your retreat!
Listing is courtesy of: BHHS FLORIDA PROPERTIES GROUP (727-847-4444)
Listing Agent: Fonda Dillard (813-514-5222)
135 W CYPRESS CT, OLDSMAR, FL 34677
$2,100136 Days on yellowkey MLS ID: TB8471216
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1054 Built: 1980Community: East Lake Woodlands Cypress EstatesSpa: NoCondo
Remarks: Call to see this East Lake Woodlands Finest 2 Bedroom 2 Bath cute downstairs corner condo with almost everything new. Including most of the windows. Treat yourself to elegance in this remodeled Kitchen with LOTS of cupboard space and Quartz counters. New cabinets and lighting. Walk in to see the beautiful flooring throughout the condo. The large Master Bedroom has 3 closets and room for a King size bed. The guest room is separated by the closets and both baths. A small Pet is welcome under 20 lbs. Reserved space right in front of the building. Close to all kinds of shopping in the Eastlake corridor. Great Schools and gated community. Usually commute 25 minutes to airport or 20 to the beach.
86 PELICAN DR N, OLDSMAR, FL 34677
$1,45068 Days on yellowkey MLS ID: TB8506405
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 864 Built: 1984Community: Gull-Aire VillageManufactured Home
Elementary School: Oldsmar Elementary-PN
Remarks: 2/2 home in Gull-Aire available for rent immediately. Gull-Aire is a 55+ ONLY socially active community with a clubhouse, library, pool table, shuffleboard, Bocce ball court and heated pool and spa. The clubhouse has planned events every month. There is always somewhere to practice Yoga, do pool exercises, play Bingo, cards, and go line dancing. The community is golf cart friendly. One pet. retail plaza just across the street from the community. Close proximity to Mease Countryside Hospital. 10 miles from Honeymoon Island/Caladesi. Walking trail along the canal includes 2 access points from within the community. Room sizes are approximate and to be verified by the tenant/tenant's agent.
Listing is courtesy of: LIPPLY REAL ESTATE (727-314-1000)
Listing Agent: Adnian Rakanovic (727-858-7882)
112 LINDSAY LN, OLDSMAR, FL 34677
$2,50083 Days on yellowkey MLS ID: TB8501797
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1626 Built: 1985Community: St Andrews CondoSpa: NoTownhouse
Remarks: Call me today to book your short-term rental! in East Lake Woodlands. Thinking of moving to Florida? NOT AVAILABLE FEB TO APRIL 2027 Try before you buy with a short-term stay in beautiful East Lake Woodlands! This fully furnished 2-bedroom, 2-bath upstairs condo, complete with a loft that includes a trundle bed and/or space for a home office. Whether you're staying for a month or up to three months, this is the perfect opportunity to explore the area and figure out where you want to live long-term. Just bring your clothes and groceries—everything else is here! Located in the highly desirable, gated East Lake Woodlands community, you'll enjoy a serene golf course setting with every comfort of home. Step out onto your extra-large screened lanai and watch the golfers pass by, or enjoy your front screened balcony overlooking peaceful surroundings. Reserved covered parking and guest spots are available for your convenience. Included in your stay: All utilities (electricity covered up to $100/month), Water, sewer, trash, High-speed internet and cable TVs in both the living room and primary bedroom In-unit washer and dryer. Both the primary bedroom and the living room offer gorgeous views of the East Lake Woodlands golf course, adding to the relaxing atmosphere of this lovely condo. Located just minutes from shopping, restaurants, a local theater, and with easy access to Tampa International Airport and Florida’s world-famous beaches, this is the ideal spot for a temporary stay that feels like a vacation. Ready to experience the East Lake Woodlands lifestyle? Call me today to book your short-term rental!
109 PINE CT, OLDSMAR, FL 34677
$2,300114 Days on yellowkey MLS ID: TB8490609
REDUCED by $200 (8.0%) on 04/08/2026
Remarks: OFFERING FIRST MONTH FREE WITH A ONE YEAR LEASE! Welcome to this beautifully maintained 2-bedroom, 2-bathroom condo located in East Lake Woodlands, a sought-after gated and guarded golf community in Oldsmar. This inviting home features an open floor plan that seamlessly connects the living, dining, and kitchen areas—perfect for both relaxing and entertaining. The spacious primary bedroom offers a walk-in closet and a cozy alcove ideal for a home office or reading nook. Both bedrooms feature brand new vinyl flooring, adding a fresh, modern touch along with durability and easy maintenance. A second bedroom and full bathroom provide comfort and flexibility for guests or additional living space. Step out back to enjoy your private screened-in patio, perfect for morning coffee or unwinding in the evenings while taking in the peaceful surroundings. Enjoy the security, serenity, and lifestyle that come with living in a well-maintained golf community—conveniently located near shopping, dining, and beautiful Gulf Coast beaches. Schedule your showing today!
Listing is courtesy of: COLDWELL BANKER REALTY (813-977-3500)
Listing Agent: Scott Corr (631-992-1927)
3063 ST CLAIR AVE, OLDSMAR, FL 34677
$1,500113 Days on yellowkey MLS ID: TB8491085
REDUCED by $150 (9.1%) on 04/07/2026
Bed: 2 Bath: 1.0 Gar: 1 Liv Area Sq Ft: 700 Built: 2006Community: West Oldsmar Sec 1Apartment
Remarks: Charming apartment in desirable Oldsmar featuring two spacious bedrooms and one full bathroom. Enjoy the convenience of an oversized one-car garage, a large inviting deck, and a fully equipped galley kitchen. INCLUDES ALL UTILITIES!!!—yes, even internet and electricity—making for truly hassle-free living. Ideally located just minutes from Tampa International Airport and within easy reach of Pinellas County’s beautiful parks and beaches.”
Listing is courtesy of: TOM TUCKER REALTY (727-692-3997)
Listing Agent: Tom Tucker (727-692-3997)
284 WOODLAKE WYNDE, OLDSMAR, FL 34677
$2,000102 Days on yellowkey MLS ID: TB8494637
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 924 Built: 1985Community: East Lake Woodlands Woodlake RunSpa: NoCondo
Remarks: Call to see this stunning East Lake Woodlands furnished short-term rental! This updated 2-bedroom, 2-bathroom upstairs unit boasts vaulted ceilings and two relaxing balconies. Enjoy the serene view of the large pond from one balcony and watch the lively activity at the pool from the other. Simply bring your clothes, food, and a great attitude. Everything else is provided. The bedrooms are split for added privacy, and reserved parking is conveniently located right up front. A washer and dryer are also included, and all utilities, internet, and cable are covered. This beautiful property is close to shopping, theaters, and numerous restaurants on Tampa Road and East Lake Business. Plus, it's just a short drive to the airport and the beaches. We will consider a small pet. Available now through December 2026 only. Don't miss out on this fantastic opportunity!
106 MEADOW LN, OLDSMAR, FL 34677
$1,695180 Days on yellowkey MLS ID: TB8465265
0 Days Off yellowkey (back on 3/25/2026)
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 879 Built: 1985Community: East Lake WoodlandsCondo
Remarks: Welcome home to this updated unfurnished second-floor condo located in the desirable Gated community of East Lake Woodlands. This two bedroom, two bath condo features an open floor plan with a split bedroom layout, offering privacy and flexibility. The condo has a nice eat in Kitchen with pantry. The Kitchen overlooks the bright living and dining areas. Sliders flow seamlessly out to a screened lanai overlooking a green belt, perfect for relaxing or enjoying your morning coffee. A laundry closet including a washer/dryer for use is located on the lanai & adds every day convenience. Both bedrooms are well sized and the updated interiors provide a clean modern feel throughout. You will find the primary bedroom has a walk-in closet and two additional closets. Also an ensuite bath featuring a walk-in shower. The guest bath has a tub/shower & is steps away from guest room. Water, sewer, trash, basic cable, and Internet are included in the rental rate! This adds Great value! The community pool is a short walk away. Newer Hurricane rated Windows & and Doors adds thermal & sound barrier protection. East Lake Woodlands is conveniently located near Shopping, Dining, Medical, Entertainment, Parks, Beautiful Beaches and easy access to Clearwater, Tampa, St Pete Airports.
Listing is courtesy of: TAMPA BAY SIGNATURE PROPERTIES, LLC (727-692-2847)
Listing Agent: Christi Watson (727-692-2847)
20 EMERALD BAY DR, OLDSMAR, FL 34677
$1,995193 Days on yellowkey MLS ID: TB8460835
0 Days Off yellowkey (back on 3/9/2026)
Bed: 3 Bath: 2.0 Liv Area Sq Ft: 1264 Built: 1996Community: Emerald BayTownhouse
Remarks: Updated, 3/2 Townhouse in Oldsmar available for now! Master bedroom downstairs, 2 bedrooms upstairs. 2 parking spaces under carport come with the unit. Located on a pond, with dock in back. Newly painted, dark wood like ceramic tile flooring downstairs. New carpet on stairs and entire 2nd floor. Beautiful water view from master bedroom.Washer and dryer included.Small pets (under 20 lbs) allowed at owners discretion only. Won't last long!
Listing is courtesy of: LISA HALL REALTY, INC (727-742-5830)
Listing Agent: Jeffrey Hall (727-744-3610)
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